Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer)

27 Apr 2025 · 1 h 32 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Podcast Summary: Lenny's Podcast - Inside monday.com’s Transformation with Daniel Lereya

Episode Overview In this episode of Lenny's Podcast, Daniel Lereya, Chief Product and Technology Officer at monday.com, shares insights on the company's transformation into a $1 billion ARR powerhouse. The discussion encompasses their strategic pivots, team culture, and innovative practices that propelled their growth.

Key Learnings

  1. Radical Transparency:
  2. Sharing metrics openly fosters a culture of accountability and engagement among employees.
  3. Transparency helps unify and align the team around common goals.
  1. Ambitious Goal-Setting:
  2. Setting seemingly impossible targets can unlock innovative thinking and drive extraordinary results.
  3. Example: The team aimed to develop 25 new features in a month, resulting in the rapid deployment of new columns.
  1. Impact Over Output:
  2. Focusing on the impact of features rather than simply shipping them has transformed the company's culture.
  3. It's essential to understand how new developments affect users and measure success based on real-world impact.
  1. Time-Boxing and Focus:
  2. Implementing "traps" or deadlines pushes teams to prioritize and maintain focus, minimizing scope creep.
  3. Time-limited projects encourage quick iterations and feedback.
  1. Embracing User Feedback:
  2. Engaging user feedback is critical in product development to ensure real-world applicability and relevance.

Pivotal Moments

  • Competitor Awareness: Daniel discusses the moment they realized competitors were shipping faster and how it catalyzed a transformation in their internal operations.
  • Crisis Management: Lereya shares stories of performance issues that forced the team to rethink their infrastructure, leading to significant long-term improvements.

Detailed Discussions

Transformation Due to Competition

  • Daniel recounts the moment of realization when competitors launched numerous new features, leading to an internal reassessment of their pace and strategies.
  • The company adopted ambitious goals, pushing the team to think differently and innovate rapidly.

Culture of Accountability

  • Transparency in sharing company metrics, even during interviews, creates a sense of partnership among employees.
  • Daniel emphasizes that radical transparency equips employees to tackle challenges collectively.

Navigating Growth Challenges

  • Discusses the importance of adapting leadership styles and recognizing when personal strengths may become weaknesses as the company scales.
  • Emphasizes the importance of maintaining a focus on impact to drive product development.

The Power of AI

  • Daniel highlights the use of AI tools in day-to-day operations, such as leveraging AI for competitive analysis and decision-making.
  • He shares personal anecdotes about the benefits of AI in understanding complex information quickly.

Conclusion Daniel Lereya emphasizes the importance of a strong culture, bold decision-making, and a relentless focus on impact to drive successful product development and company growth. He encourages leaders to embrace radical transparency, set ambitious goals, and remain open to feedback to cultivate an environment that thrives on innovation.

Recommended Actions for Listeners

  • Foster a culture of transparency in your organization.
  • Set ambitious goals to inspire innovative thinking.
  • Focus on user impact rather than just feature output.
  • Embrace feedback loops to continually refine and improve products.

Where to Find Daniel Lereya

  • [LinkedIn](https://www.linkedin.com/in/daniel-lereya-aa487646/)

Additional Resources

  • Podcast Episodes: Listeners can find more insightful conversations on product management and growth strategies on Lenny's Podcast.
  • Lenny's Newsletter: Subscribe for actionable insights and advice on product and growth.

Join the conversation on [Lenny's Podcast](https://www.lennysnewsletter.com?utm_medium=podcast)!

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00A great plan, basically for me, is someone that is relentless until he gets this impact, until he validates that this impact is in place. In some cases, doing the biggest impact is not developing another feature. It's about making the current value more accessible. Even at this for eight years, you said there's 250 ,000 customers at this point. What would you say is the most counterintuitive thing you've learned through this journey of building Monday? We really have a bit in the porch of very radical transparency about everything. Before we went public, we actually shared every bit of information with our employees.

0:36Instead of demoralizing people, I think that this is something that gives them a sense of deep partnership. We really want everyone's brains in the challenge and not just one centralized brain in a lot of walking hands. You basically realized that your competitors were shipping a lot faster than you were. that made you shift the way you think about product and the way you operate. Some of our competitors did something that we can only imagine we said, okay, we need to treat it differently. We received a gift from our competitors. They showed us that it's possible. Use your competition, know it and take it and set ambitious goals and believe in yourself and you can do amazing things.

1:14Today my guest is Daniel Aureia, Daniel's currently Chief Product and Technology Officer at Monday .com. He joined when they were just around 40 employees, and a few years in, Daniel and the executive realized that their competitors were able to move a lot faster than they were and ship a lot more often than they were. And that spurred a transformation in how they build and operate their teams. Very few companies are able to transform like this, and even fewer recognize that something is wrong. In our conversation, Daniel shares a bunch of very specific insights and suggestions into to how to go about making change or even recognizing that something is wrong.

1:50Daniel shares moments when it felt like everything was going to crumble. Why it's important to know that the skills that got you to where you are today aren't the skills that are going to take you to the next level. Why it's so important to orient all your teams around impact and so much more. Vindray this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of paid accounts at superhuman, linear, notion, granola, and perplexity pro. Check it out at Lenny's newsletter .com and click bundle.

2:21With that, I bring you Daniel Aureia. This episode is brought to you by Interpret. Interpret unifies all your customer interactions, from gong calls to zen des tickets to Twitter threads to apps to reviews, and makes it available for analysis. It's trusted by leading product orgs like Canva, Notion, Lume, Linear, Monday .com and to bring the voice of the customer into the product development process, helping you build best -in -class products faster. What makes Interpret special is its ability to build and update customer specific AI models that provide the most granular and accurate insights into your business, connect customer insights to revenue and operational data in your CRM or Gata Warehouse to map the business impact of each customer need and prioritize confidently, and empower your entire team to easily take action on use cases like wind loss analysis, critical bug detection and identifying drivers of churn with interprets AI system wisdom.

3:15Looking to automate your feedback loops and prioritize your roadmap with confidence like notion, canva, and linear, visit ENTER, P -R -E -T, dot com slash Lenny to connect with the team and to get two free months when you sign up for an annual plan. This is a limited time offer that's interpret dot com slash Lenny. This episode is brought to you by air -table Product Central, the unified system that brings your entire product org together in one place. No more scatter tools, no more misaligned teams. If you're like most product leaders, you're tired of constant context switching between tools.

3:50That's why AirTable built Product Central after decades of working with world -class product companies. Think of it as mission control for your entire product organization. Unlike rigid point solutions, product central powers everything, from resourcing to voice of customer through road mapping to launch execution. And because it's built on AirTables no code platform, you can customize every workload to match exactly how your team works. No limitations, no compromises. Ready to see it in action? Head to airtable .com slash Lenny to book a demo. That's airtable .com slash Lenny.

4:28Daniel, thank you so much for being here and welcome to the podcast. Thank you so much for having me. We're gonna get into the story of Monday. We're gonna talk about your journey over the last eight years, building and scaling this company, and all things you've learned along the way. But I wanna start with a very specific moment that you shared with me, where you basically realized that your competitors were shipping a lot faster than you were able to get stuff out a lot more quickly and more often than you guys. And that made you shift the way you think about product and the way you operate.

5:01Can you talk about that moment and that lesson and what she took away from that? Yeah, well, you take me a while back, you know, I think it was when we were relatively a small team. I think we were something around like 30 people and you know, including engineers and products and everyone. It's actually that back in the days, we did so many things and actually, we had an amazing, amazing execution where they, you know, weekly update, we would share everything that we did with the company. I mean, it was always, always, you know, super long and super like with so many different things. And we really felt good about ourselves at that point, to be honest, about the execution.

5:49And then I remember one day, you know, coming to the office and just looking on one of our competitors. And with Monday we have like one of the main things that we have in the product is our boards. It's like the heart and soul of the product and it's you can think about it as a table and it has different column types, data types that you can capture within the board and work with. And you know back then we had five of these and I was is actually coding the sixth one to be honest. And each and every one of these took us four months to develop together with defining the products and everything.

6:30And at this morning, we actually saw that one of our main competitors back then has actually launched 30 new columns. 30. Yeah. And we said, OK. At first we didn't really know what to do and we thought about it and I remembered that even we said okay we are going to take even some time out of the office so back then Oyan and Ran which are the founders and also together with me and Tal which is one of the main techlets in Monday for a long time and few others we went outside the office and we said, listen, we need to do things differently. Something doesn't make sense. And remember back then that for me, this realization of a understanding that we are doing so much, but suddenly, some of our competitors did something that we can only imagine and actually transform the product because it's a different type of platform if you think about it.

7:40It was really hard, personally. First of all admitting that although you walked like crazy, you didn't do something that really transformed the product because I remember back then when we did a conversation, we said, okay, we're doing so much. What is the most meaningful thing that we did over the last three months? And suddenly the answer was, there's so many things, but it wasn't something specific. And after like, you know, acknowledging that and, you know, it's a very hard thing personally, especially when you work so hard and you put your entire heart in what you do, we said, okay, now we need to treat it differently.

8:26We received a gift for more competitors. They showed us that it's possible. Now we need to think how. And in order to do that, we need to think differently because remember, like we said, okay, if we're going to add 25 more multiplied by four months, we're a small team. We lost, okay, we can't make it. So we said, okay, we need to take upon ourselves an ambitious goal, like 25 columns in one month. And this is the goal that we took upon ourselves. And you know, I think that the fact that our competitors did it, didn't give us the excuse of saying it's not possible. So in a way, it was the biggest favor that we can ask for.

9:13And you know, long story short, month and a half afterwards, we had 30 columns in Monday. And we did it by thinking totally different. And by the way, afterwards, we did it over and over again. So if you think about Monday, it's basically a platform for work and you have different building blocks Columns is one of them, but we did the same drill exactly with Dashboards and widgets and then with automations and so on. So I think this was so transformative because Hey, we understood that you need to constantly think especially at these phases How we how would you transform completely the product in the next three months?

9:54And if you can't answer that and you say listen I'm doing so much thing but you can't point this thing You have a focused problem in my eyes and second that is that you know Put ambitious goals It will make you think differently and you know really love now to do it even with when we don't know it's possible And it actually like works for us time of the time and Let's think about it. You know the team that was there suddenly became invincible because you know it's such an amazing amazing experience that you have a goal that you don't know how you're going to do it and you succeed and then it makes you feel that everything is possible.

10:40There's so much here and I have so many threads I want to follow in. One is just there's the kind of things there's as a metaphor of the four minute mile where no one thought it was possible and then someone did it and then everyone started beating that record. So I like that this is highlighting there's just so much power and seeing somebody else accomplish something you thought was impossible and then locks the way you think and I love that you saw as a gift a lot of people a lot of companies do this they're in this place and they're like no way it's like when the iPhone launch like no no one no one needs that that's not there's no keyboard and a lot of people like are like deny that it's a thing they should be paying attention to I love that you saw it is like okay we need to we need to move the things have changed we're not doing things We're not going to be competitive long term.

11:23I think it's also very much about focus. And I think that, you know, it's very hard to get to a very good execution, but it doesn't guarantee that you are working in the right way. And many times in my eyes, you know, simple questions can provide the most and the deepest insights about your work. And I think that for us, the fact that we managed to leverage it, as you said, and see it as a gift is one of the most important things. use your competition, know it, use it to your advantage and you know take it and set ambitious goals and believe in yourself and you can do amazing things. Another right I think peace a lot of people probably resonating with here is starting a company that's small growing things are going great and then all of a sudden things start to slow down and in some cases you don't realize that they've slowed down and that's what happened in your case sounds like in a lot of cases what founders like, what the hell's going on?

12:18Why is it taking three to four weeks to ship one type of cotton you call them? And so is there anything? By the way, what was the scale of the company at this point? Well, it's a good question. If I'm not mistaken, it was around 2018 back then how it's safe to assume like 150 to 100 people in the company, but we were relatively small. I recently had Brian Singer on the podcast who created the shape up method from base camp and that's kind of his piece of advice to you is around like 50 to 100 people. Things start to really change and slow down and that's where a lot of companies start to go sideways.

12:56So that resonates. That's really interesting. And by the way, these columns you're describing just to make it clear, this is like a new type of like data, like new format of column. Like it's a new data format that you're building. It's not like just add another column to some database. Yeah. So actually, like, exactly. It's a new type of column, but it's a whole product around it. If you think about it, for instance, you have a column that captures dates, so it's pretty straightforward, but you can also have like formula column, which is like more complicated and has like more complex product around it.

13:28I think one of the best benefits for us as platform is that suddenly when we will like, when we set the goal of adding so many different columns, we actually stopped for the first time and say what is a column like and we also like organized all the product architecture around it and you know these kind of things like sounds really trivial in retrospect but you know we really define okay each column need to have like specific capabilities it should be able to export it to Excel it should be able to be filtered and sorted and so many different other things but basically we defined what is it and then create an infrastructure for all these shared things, making the work of adding a new column, just thinking about the specific product that you want to provide with each one of these columns.

14:19And the story about it is actually even more interesting, the way we actually achieved it is that we said, okay, in two weeks we're going to have an Akaton in which each one of our developers is going to take one column and implement it in one day. And you know, if you think about it from four months to one day, it's like mind -blowing and back then I remember people said how can it be but then tell that I told you about build an infrastructure, it sent it to me, I did a column at night, you know just to see how it works and on the day that we did the columns like everyone knew what they are going to do, what they are trying to solve and we just did it and two weeks afterwards it was in production, which was amazing.

15:11Well, we want to do here is help people avoid these moments where they're almost like too late and realizing the things have slowed down. So I think a really another important lesson here is the power of ambition and thinking crazy, a big a lot of people think that when you ask your team, we need to build 25 columns in a month or whatever it was. People would be like, I burned out or feeling super depressed, but really people get excited. There's all this opportunity to think really differently. It reminds me of our B &B Brian Chesky was very famous for you. Give him a goal. Here's our goal for the year.

15:42And he's like, what would it take to 10x this goal? Just like, what would it take to do that? And he's always pushing you to think a lot bigger when you're like, because your first reaction's like, what? No, no. Why? Which, sleep was alone. But then you realize if you really think big, it changes everything about how you approach the problem as you describe where it's like instead of like in a date. What would it take to build this in a date? Yeah, and I think by the way, this is something which is really important about setting the vicious girls If you'll set them it like a different girl. I want to reduce it from four months to three months So many times this translates in people heads to I want you to walk harder I want you to walk longer hours and this is not a message here It's about working smarter and I think that many times when we talk about speed of execution There's fake speed, which means trying to do the same work by skipping stages or not doing the high quality that you want.

16:39But there's the real speed and speedy, like organizations and speedy of execution. Many times it's about doing things right, it's about understanding, what is going to move the needle and work only on death, not working on a lot of things that you tend to invent when you're trying to solve a problem and being is like you know about like thinking as you said like thinking differently and I think that for the girls this is why we really wanted the girl that you really understand from the first minute that if you look the same way you cannot achieve it even if you will slip in the office so you need to change dramatically how you think and And you know, the advanced phase of it is that today, we're doing it on things that we didn't see others doing.

17:33And you know, we have the confidence because we have the experience of like trusting ourselves that this is an exercise for us that will make us actually think about different solutions. I know another element of this that is really important to you that you have shifted the way you operate is focusing on impact. There's a lot of focus on just building a lot of stuff and you realize there's a lot of power and thinking from perspective, how do we have the most impact? Talk about that. This is the core and the main thing that we also measure like our teams. And this is how I see a great PM. So a great PM basically for me is someone that is relentless until he gets this impact and until he validates that this impact is in place.

18:18And you know, for us, it really change how we think about things, it really changed how we set goals for our teams. So in many ways, PM in Monday, first and foremost is responsible for creating the shared understanding on what would be impactful for our customers. Okay, it's not about the solution and what we are going to build. It's about what's the problem, what's the opportunity, and second, how we will know that we've moved the Nailer. And without these two things, you can build so many different things and And it's like songs for the draw. Like I built such huge part of what I built was never used by users the way I thought it was going to use.

19:02So I think that for me having this understanding of what we want to change for our customers and also how we know we did it is a huge huge part of the IPM all. And for us, it means that we pay a lot of time in setting goals, in making sure that we really understand both, again, the opportunity, but not only that, but how we'll see, and we'll know for sure that we move the needle in many ways. It changes the conversation. So PMs and their teams, many times like are spending a lot of time at the problem area, Before they think about the solution, the solution is not the case anymore. It's not like there are so many different solutions and Once you do that and you have these goals suddenly it produces also a lot of the discussions that you have about the different solutions Because everyone knows that everything is going to be tested on real life.

20:01So they make Make it everyone pre -definitely and also in that way, you know it makes you think much more holistically, which I also think is something that is very special at Monday is that we give our teams like real -life goals as much as we can. And then you know in some cases doing the biggest impact is not developing another feature. It's about making the current value more accessible. It's about connecting better to the go -to -market motion that you have. It's about understanding how your customers are going to learn what you built and use it. And you know, this realization is something that we try very hard to stay on it.

20:49And it's hard because like people tend to build things like we all love to build things. Right? And when you start to build things, you get excited and suddenly you lose track of why? Why are you doing it and why do you need to change? And I think that in that sense, this is the most important part about like this point of impact. And you know, this is also how we measure ourselves. So we can work extremely hard. It doesn't mean that we are successful. It doesn't mean that we are doing our work right. Okay. And it's not only for the PMs. It's for the entire team. So the entire team succeeds or fail together based on the value that we bring to our customers.

21:30and we have a lot of different ways in order to make sure that we stay honest to this principle. There's a lot of people listening to this that work at say modern tech companies, very high growth tech companies that are just like duh this is how you should work. A lot of people hearing this are like I don't really understand like how like what am I doing wrong? What am I missing maybe? What's a sign that you're not oriented around impact? I think the most obvious sign for me is that you are building something without the aim or without the initial aim of what it changed for your users and how you are going to measure it.

22:12So in my eyes, it's many times the fact that you don't have a goal. Or the goal is like many times, you know, for me, a smell for that is that I hear people use the word we're going to enhance. We're going to augment. We're going to extend value and distance and it's not enough. What is it going to change for users and how you are going to see it? That it actually happened. And then you start asking yourself all the questions, right? because once you have a girl that you are committed to, suddenly you think about the target audience because you need enough like big enough target audience for instance in order to get to your goals.

22:53You need to make sure that what you build actually going to touch all of these people. And I can share just a recent example. And you know, these things sound trivial and maybe an example would help resonate with that because I know many people are thinking like that. And we have a very interesting offering that we're just introduced with AI. It's called AI blocks. And basically, it means that with no code, you can integrate blocks, which contain AI actions within your existing workflows. And you know, 70 % of Monday's customers are non -tech. And for them, this makes AI accessible for them and has a huge, huge value.

23:37And we started building these blocks and we released it to customers and we measured, you know, discoverability and adoption and retention and so on. And something that we do in order to stay connected to the numbers. So each team at Monday has like what we call the daily numbers update. So we have a think about it like a message that the team is building with all the numbers that they care about because we really want people to live this number. So for AI, for instance, for AI blocks, it was AI actions. So we had AI actions, how many accounts, like I were using these AI actions and so on and so on.

24:19And you know, we got amazing responses from our customers. We see great success of them getting value from AI actions. But you know one day like in this like it's a we use a select channel in which And one of our internal systems big brain is sending us this message as every day and then we have conversations about it Okay, and you know one day we saw We noticed that the amount of accounts that are using AI is super super low comparing to the entire population that we have And you know, we have 250 ,000 paying companies that use Monday and we saw only like few thousands there. And you know, until this point, everyone will like in a very good feeling that we are making an amazing product, we get really good feedback, we are building great value, we are adding value.

25:14But we sit down and say, okay, why it's only like this and this, then someone say, yeah, you know since AI is new, we need to do change of the terms of service for customers before we are opening it to them. And this is planned, you know, for like in the next quarter or something like that and said what? No, we need to do it now. You know, we need to now open it for everyone because this is actually what would be the most impactful thing to do. And then like you know the team went and set with legal and sent with everyone and with two weeks time it was open to 98 % of Monday customers you know.

25:59And I think in that sense you know this is a very good example because we could have continued building value and it's great but the impact wouldn't be the impact that we were aiming for. And this is a very important point. And you know we I think in that sense staying really connected to your teams to your number. So this is something that I really feel strongly about. I feel that you need to get your numbers in push. You need to live by them. And you know, for me, it's like so exciting to see a conversation that says, oh wow, today There were a lot of new accounts that are using what I'm building.

26:39Let's see what it happens And you know, this kind of things that I see the conversation about It's amazing and also you know for in this case seeing the i actions go It's like you want to dive it and push it forward and in many ways they feel that This is a very good example on where you can actually build a lot of value. You can walk really fast. You can deliver a lot of features, but the problem lays in other place in order to get the impact that you want. Yeah, there's so much joy in watching her number go up. So just to close the loop here, to help people see if their impact driven, working from a perspective of how do we drive the most impact, is one simple way of thinking about it is you're working backwards from a goal that is going to drive business growth and revenue basically in the end.

27:28If you're working backwards from a number and a metric and a goal and then thinking through what are the levers that will most move this metric that's assigned your thinking impact through by impact versus let's just keep shipping features that the sales team wants. Yeah and I think another thing for me like it's an exercise that I really you know I really encourage everyone to do for me it was like after the columns hackathon and everything that we talked about I said okay each quarter and this is when we were much smaller but it can be each month it can be each two weeks but how do I imagine the company and the product is going to be different and better for customers in a quarter from now and from that you know work it backwards but if you are just saying we'll have better security, we'll have better performance, we'll have less bugs, we'll have more enhancements to the, I don't know, this and this feature, it's not enough.

28:29You need to constantly build value, which is pivotal to your customers. And if you don't do it, and if it's helpful you to answer about this question, it's a very good sign that you are not impot -driven. And you know, I love to do it. Also with Tim's and individuals, you are like, what are the things that you are most proud of that you did in the last three months? And if it's like takes you a lot of time to think, you're not very focused and you're definitely not maximizing the impact that you want due to that in my eyes. I like that exercise as kind of a like versus waiting for your competitors to do something and then realizing that it would be way behind it's forcing yourself every quarter to think about this.

29:09So do you do this as like a meeting or or some in your calendar or how do you had he actually operationalizes. So it's actually, you know, today we are like under the Builders organization, which is the engineering product management product design was 700 people. So we have a lot of different, like, ways and methodologies to do it in different levels. But I'll give you an example from the company level and from the team level, maybe, because these are the most interesting ones. So So we just recently had an early kickoff, each and every year we do an early kickoff for our company. And one of the most exciting sessions obviously is what we are going to do with our product, as a product company.

Read the full transcript

29:52And I really like to have a slide in which I like write and I just share it when I'm going to stand here in the ear form now. What is going to be different for our customers? And you know, this is on the company level and I have one slide and it talks about like our offering and it talks about the value that they are getting in a way that next year, I want to, you know, it's here to start my presentation with the slide from last year and see where we are. And you know, in this level, it can be something like our CLM continues with a very strong momentum and becomes a product suite when we give much more robust value to our customers.

30:36This can be an example with an additional product of CRM marketing. I would just say. On a team level, what we did, and maybe I'll take an example from the early days, we really loved to do each and every two weeks. I told you we would write like an update for the entire company about what we did. And the way we did it is that each and every one of our team members actually for right what is highlights. And then we would share it with the company. And this exercise really made us sit every two weeks and think on an individual level, but also on a team level. And you know, every one of our team members used to write to read these updates and say then we had a good two weeks or we had a bad two weeks we did a lot of impact or we did not not enough impact.

31:35So I really encourage to create these points in time when you sit down and you force yourself to understand whether what you did is what you thought you're going to achieve or not. That's great. I really like the slide idea. It's basically there's all this power and just working backwards from something in the future. However, you come up with it. So it's just like in a year we're going to have this just like working backwards from a goal, working backwards from a big vision. I think those are such good exercises, you know, obviously Amazon's famous working backwards is all book called working back from their PR approach.

32:08Okay, I want to go in a slightly different direction. I want to zoom out a little bit. So even at this for eight years building Monday, You said there's 250 ,000 customers at this point. What's like the revenue scale? Give people a couple stats to give them a sense of just how large this company's gotten. We recently announced that we cost the one billion dollar in ARR. And we're serving, as I said, 250 ,000 customers across the globe from virtually any industry that you can think about, like more than 200 different business verticals. It could be both tech and non -techs, every customers. The vast majority of our customers are non -tech.

32:49And you know, from like a customer that is building airplanes and cruise ships all the way to real estate, construction, finance, tech, and everything, you can basically think of. And if I like just for reference and single golf pay, so when I joined Monday, eight and a half years ago, And we, back then we were called the pulse. We had around 4 million in ERL and we, you know, we scaled from there to 1 billion. And from like around 30, 40 people to the company to 2500 right now. Awesome. When you talk about the product you're building, it's a lot of people it's like, oh, it's like project management stuff.

33:34All this like column, like what's the big deal? But I drew a house that on the podcast and you made this really interesting point. when he talks to people working at SpaceX who are like launching rockets to Mars, and he talked about people building ships. Like, if you really boil down what are they doing day to day, they're sitting in tools like Monday, putting together tasks and doing to -do's and sharing documents. Like, this is kind of what the world runs on. So it's important to have that perspective with that, putting that aside for a second. I think very few people have seen what you've seen.

34:04It's having a, seeing a company skill this way. Also, the transformation you just shared of just like almost shipping too much and being slow to like, okay, let's rework things to shipping 25 columns in a month and all these things. Like, very few people I've seen this. So there's a lot to learn from this journey that you've been on. So I have a bunch of questions and a different, a bunch of different ways of approaching some of your biggest lessons from this journey. The first is, let me just ask you this question. What would you say is the most counterintuitive thing you've learned about building product and leading teams through this journey of building Monday.

34:39Maybe first of all is about something that we really care about which is transparency. I'm like let me tell you a story. I sat down for dinner at my family and many, many different members of my family are like entrepreneurs, so like working as an executive in tech companies and so on. And you know, back in the days, we as Monday, before we went public, we actually shared every bit of information with my employees. You would get into our office and you would see a dashboard with how many paying accounts you have, how many people have chained today, how many signups do we have and so many different things.

35:24Even if you came for an interview, you would see these numbers. And I remember sitting in this dinner and everyone would tell me, listen, you are making a mistake. How can you do it? When thing goes south, you know, you'll demoralize the team and people like, you know, we'll get upset about it. And I think this is, you know, for me, one of the most important things, when you hire and you have such a talented a team, you want to share them, we want to share with them everything. And the reason for that is that then you are working on every challenge together. And instead of demoralizing people, I think that for the right people and the people that like you know, are working at Monday, this is something that gives them so like you know, a sense of deep partnership.

36:16And as a leader, you know, there will many situations in my professional life that I knew some bit of information and I felt you know all the way on my shoulders and I love to call it the dark side of the moon or they're alone, right? Like you're coming to the office there's nothing you know like more demoralizing as or like depressing as a leader that you feel awful because something that you know and you're coming to the office and everything is great and everyone are like happy and I think in Monday we really wanted to do a different plan. We really have a little approach of like very radical transparency about everything and this actually makes everyone part of what we are doing and in a way we like to say we really want everyone's brains in the challenge and not just one centralized brain in the network working hands and I can share examples you know when for instance suddenly people would come up to the office we have dashboards across everyone in the office like each team has its own dashboards we have our company dashboards with format or x and so on and I remember cases in which someone said listen what happened to the conversion and you know think how powerful it is when you have everyone at the company looking at these things and many of the things that we discovered many of the things that we the size, challenges and problems is things that people saw due to distance transparency.

37:48So I think that maybe the, you know, counter -intuitive part is that don't be afraid to share the information. It's exactly the other way around. And I can probably share that, you know, even today's public company. We really share everything that we can, you know, and also like if you are product manager at Monday, you are signing like a 10 -by -5 program for selling your stocks, meaning that we found a way to make everyone still see the data because we think this is the most important part. And I think this is one thing that I really believe in and really changed how we work and also how people are feeling about being partners in building Monday and not just walking at a company.

38:36Is that thing they sign that's just like auto cell stocks so they're not selling based on information based on announcements that's coming. Okay, God, it's every PM basically has to automatically. I can't like decide I'm going to sell my stock tomorrow because of this numbers thinking. Yeah, so you know, like we want to give people the choice but like usually we really feel that in most cases you really need to know this information in order to do your walk. And so interesting. And I think people even prefer just like dollar cost average. So you know, it's like, it's like easier not having to try to time all these things.

39:11I definitely think so. Yeah. That's really interesting. And that's just product managers or how far does that all go? No. So basically when we became public, you know, I remember still like one of the conversations that we had with like the bankers and the lawyers about like listen guys things would need to change. You cannot have a dashboard with only your financials at the entrance of the building. It doesn't make sense as a public company and we understood it but we didn't want to let go of what we cared about because we really believe this is one of the main drivers to the business having these to expensive and having these like shared brains you know and mode so we tried to think about ways in order to do it so now if I like fast forward you know we're almost four years public and we have an internal app called Monday morning and in Monday morning you have two parts parts A and part B part A is for the every company employee contains a lot about engagement and a lot of data that can be shared with everyone.

40:24And part B is confidential and it's by role. Okay, so it's their company management, but I think the important point is that we see product management as something that got to have these numbers. So we thought about it really hard and you know, it's a lot of logistics to do like so many plans, then be five plans, but I think it's worth it. Yeah. This is so interesting. Like a lot of companies talking about transparency. And you guys are, I think radical transparency is a good way to describe this, because I've never heard of a company doing this. They didn't care about it as well, apparently. And yeah, it took time to, you know, to get to these solutions.

41:04That's so funny. So for people that are listening to this, like, maybe we should explore this. what's like one thing you'd suggest they could do to start moving down this road. And the benefit again is you, I guess maybe again remind people of the benefits of doing this because it sounds like a lot of work and risk. So I think that as a young startup, it's actually not such a hard work. When we were very small, you know, back in the days, we had like the daily numbers concept that we now have for the teams. We had the daily numbers for the company, how much paying accounts, how many upgraded, downgrade, and so on daily.

41:39And you saw people reacting to it on a daily basis. So this is something that you can do in virtually one hour. And it changes how people see, they're all within the company. It focuses everyone to the company's KPIs, because everyone understands what you care about and so on. So this is one thing that you can do extremely fast. And I don't see any disadvantage.

42:05And I can share it. Like, it's so much like it's even like a big relief that you don't need to think, can I share it? Can I, can I, can I, can I, like, you just let it go and everything would be okay. And I can share from my experience that we shared everything. And the second thing which is really practical, you know, it's the office dashboards. We really believe in it. So you know you buy a TV you put it on your wall You start a conversation to do it. What do we want to show on this TV? And you know when we was like a smaller startup and we set all in one office space we had our company goals Dashboard and it also had like We we programmed it to have sounds on meaningful events So when you add the like for instance new paying account you had the almost Simpson saying like the same with the one million dollar I'll become a millionaire or something like that For you know a new sign up you add the tick and so on so Suddenly everyone are leaving it, you know it becomes part of the cadence of the company So these are just two ideas to make it super easy and The change happens immediately and love how that connects back to the whole point about impact people all whining around here is what we're trying to drive.

43:22Like if the Simpson sound is going off, that's a sign that this matters and that something we should be driving up. And it creates such a partnership, you know, I remember like reaching to the first time where we had one million dollar collection in one month, breaking the record of like new paying accounts for one day, everyone are living, what in many companies, you know, only the management or the founders are like filling and I think that in that sense, you already feel that you have a great power because everyone around is the same things and it makes conversations different because everyone understands what matters to you at this point.

43:57This is awesome. Really cool counterintuitive lesson. I feel like a whole podcast could be done on how to do this effectively. I want to move on, but I guess if people want to start implementing this at the company, let's just say they should co -doc to you and you could give them a bunch of advice. I would love to. This episode is brought to you by Vanta, and I am very excited to have Christina Casiopo, CEO and co -founder Vanta, joining me for this very short conversation. Great to be here, Big fan of the podcast and the newsletter. Vanta is a long time sponsor of the show, but for some of our newer listeners, what is Vanta do and who is it for?

44:30Sure. So we started Vanta in 2018, focused on founders, helping them start to build out their security programs and get credit for all of that hard security work with compliance certifications like Sock2 or ISO2701. Today, we currently help over 9 ,000 companies, including some startup household names like Atlassian, Ramp and Langechain, start and scale their security programs and ultimately build trust by automating compliance, centralizing GRC and accelerating security reviews. That is awesome. I never experienced that these things take a lot of time and a lot of resources and nobody wants to spend time doing this.

45:08That is a very much our experience but before the company and some extent during it but the The idea is with automation with AI with software, we are helping customers build trust with prospects and customers in an efficient way. And you know our joke, we started this compliance company so you don't have to. We appreciate you for doing that and you have a special discount for listeners. They can get a thousand dollars off Vanta. Advanta .com slash Lenny. That's V -A -N -T -A .com slash Lenny for one thousand dollars off Vanta. Thanks for that Christina. Thank you. Any other big countertune of lessons from the journey that you think would be fun to share?

45:45One thing I really love about what we do in Monday is that we really love to take risks, not for the sake of it, but we are not afraid to do bold moves. And many times when you want to do bold moves, you have a lot of concerns, especially when you start to be successful because you are afraid that you are going to break everything that you built till now. And for me, you know, One of the most pivotal moments in the company life is when we decided that, you know, back in the days, as you said, we were a platform, but we had to go to market of project management tool. And we said, listen, people are doing so many different things on top of Monday, they're building a CLM with Monday and they are building a software for managing their death cycles and they are building so many different things.

46:32and we took a strategic decision to become like a multi -product company which is built on top of this platform. And we actually did something which is really counterintuitive. The first thought that comes to mind, at least for me, is why maybe not just launch a new product, do it relatively on the side, gradually understand if it's successful. and if it would be successful, double click on it. But we actually did it in a very different way. We actually announced five different new products, simultaneously, on the same time. And you know, we had so many, like, I can't stress enough how hard it is to think about it, because like I remember when we talked about and doing it, people say, what?

47:24but we are going to confuse our quanta users and it's going to have conversion and how are we going to do the marketing now when we have so many different go -to markets and the sales they don't know how to navigate people to different and what about pricing so many different consents and but we decided to do it because we really want to create a pivot a lip and I think that in that sense you know fast forward to this day like part of these products were really successful. For instance, Monday, sales CRM is like going faster than Monday, back in the days, like, you know, and it's amazing to see it.

48:03And some of them we understood that they don't need to be separate products and we collapse them back to the main product. But the point is, is that we managed to learn and to change both internally the company, how the perception of everyone around what we are building but also externally. Like this move changed dramatically the competitive landscape that we live in. And you know I think there was a lot of friction, many people at the company were like having a lot of friction with it, it was really really hard. But looking back, it's such I'm so happy with this move and the fact that we did it like that because just imagine what would happen if we would choose one of them and it wasn't the successful products.

48:48And our conclusion can be that multiportal work for us. We really manage to transform the company in a very short amount of time and also to create new reality. You know, and I think that people need to remember that and I'm constantly reminding it to myself. And I think this is something that we are constantly working, you know, with each other in order to make sure that we remember it that not taking bold risks, not making bold moves, it's a risk for itself. And many times, people want the inertia and people want just the incremental value. But if you want to do lips, many times you need to let go of things that were successful for you at the past.

49:32And this is very counterintuitive. And we did a lot of mental models to help us cope with it. So I remember that when we were small and we had for instance like 20 ,000 paying customers. So he said, listen, but most of Monday's customers are not customers of Monday yet. So we need to think about them as well. You know, and this is something that really helps you because many times you need to do things that affect like the current success that you have. But I think it's this is another very, very important thing that I'm constantly reminding to myself. There's kind of this other recurring theme that I'm noticing of just like thinking big and taking leaps and I love this point you made of Not doing that is actually a big risk not taking risk is a big risk That's a really powerful point and it's innately scary to do something risky And so I love the push here of just like Take more risks because it's so easy and this comes back again to the beginning of the conversation where you We're just like building things the way they've always been built and looking back and like what have we even done And what have we done over the year of hard work and tons of features?

50:39Think a lot of companies get in that place where they're just like, what do we like at our bean beer? I had this exact Brian's constant like, what are we even shipping? All these billions of experiments that are moving the numbers. Like what are we even doing? Like I don't know anything that we ship. That's really exciting. And so I think those are really getting rendered pushed to just like think bigger and take and you need to take big leaps. So love that. Is there any other big countertutive lessons before moving in a different direction. I really believe that many time, like spending more time on walking on something will not yield to better results or to better products.

51:15And you know, I think that many times like we as people that are building products for others, get to a point where the feedback that we want to get in the bottom of our heart, you know, is like, wow, what an amazing product you have built. And I think this is a very bad feedback to get for initial things that you are doing. Because it means that, you know, I feel that in many ways, the point in which you make real people use your product is really scary because you suddenly, you know, put your work out there and then in order to like actually, and you are afraid that they will say, listen, it's a lousy product, it's not a good product, but actually we really encourage people to get really fast production to put reps for themselves that is called by time and not by effort and you know many times I saw that more time creates more questions it creates more complications it creates more assumptions that we put for ourselves in thinking what our users need and win van things.

52:28You know, and we do it all from good reasons. We want people to like what we build. We want them to get value. But for me, like this is a very important point that many times, many times using like the setting traps mechanism of saying listen, we have three weeks. Let's think about it and scope it by time. It makes you extremely focused. And this is very important because we really want to get feedback from customers that say, yeah, listen, this is on the direction, I'm still missing this and this and this. And also we really love the fact of this is not a good product. And I can give you a recent example.

53:12You know, even when now we, you know, we work with big customers and of course, like there are different ways to implement what I said. then you are a small starter, but we are building like a new offering of enterprise work management. Think about it like a way of managing projects that you would use scale, you know, thousands of projects, like tens of thousands of employees and so on. So I really love using the deadline prep and it makes you focused, it makes you sharper and thinking and we just had a recent example with the offering I was telling you about of like enterprise work management, managing projects at scale.

53:46And you know, this is an enterprise product. So you have all the reasons in the world to say, no, I can't really sit yet. I need more time. I need to do more things. They won't use it. They need this and this and this. And I think that we actually released the first like alpha version to them. And we got a feedback of listen guys, this is premature. We need more like more comprehensive value. But we got exactly the feedback of what. And this is priceless. and my response to the team is well done. I think you did an amazing job in like releasing it and making sure, because many times being so afraid of releasing it and thinking, if I just have one, two, three more weeks, I will bid about the product.

54:32I think it's not, it's not true. This is such good advice. It resonates so much with recent other conversations I've had. So just to clarify what you're saying, basically you have a time box. When you say traps, it's basically a set amount of time. We're going to spend three weeks on this feature. And if it doesn't, if we don't hit the three weeks, we just cut scope essentially. Is that the idea? I think it's like, this is the basic version of it. But now for us, we really want and we really love doing it as an exercise for ourselves. For instance, let's say now as a public company, we say, listen, we're working on something.

55:05We want to announce it on the next turning. And put it trap for ourselves. Why? Because again, it makes you sharp. It makes you super focused about things. And, you know, I think that in many ways, this results in a much better product, because you are not building things that you invented. You are staying really to what your users needs, the real core of the value. And it's really funny to see the dynamics of teams, you know. when they are planning from the bottom up, so it starts with something that, like let's say you've done everything great, okay, you have the opportunity, you understand, you have the KPIs, everything is in place, but now they're starting to plan it.

55:49And suddenly people are raising concerns and issues and becomes a sport to say what can go wrong? And like being free -driven and then you tend to protect yourself and adding more content and more content. And then when you see what happens, it's actually like it's going to be shipped in two years. And then we say, okay, no, okay, we have earnings in two months. What can we ship to these earnings? And let's put a tab and then you suddenly see the conversation changes. First of all, it makes everyone really focused on what's the core of the value. And it removes all the theoretical discussions that people have and things like that.

56:31And you know the results are amazing and you need to remember when you do it you need to continue afterwards If you like according to feedbacks and and not let it go just but what you did in the first version But in many ways a really loved the fact that you know the first version get a feedback Which is not everything is perfect because if this is the feedback it means that we build Too much and probably it's not focused product enough and when you build a lot of features this can be like, you know, a death by a thousand cuts because in each corner of the product, you add more than you need. Yeah, there's so much here that connects the other conversation.

57:10We just had we had a car of misruff and he's CEO of captions and he made this point that if people aren't complaining about your product, like you want to see people complaining because I mean, they care. Like there's something there that they care about. If they're not here, any complaints, they could care less about what you're building and that's not that's a bad sign. I really loved it. Yeah, their company actually goes to the extreme which are describing every engineer ships a feature a marketable feature every week That's their pace I really connected to it and by the way about user feedback.

57:40I think you know It's really it's really nice because like many times you know people associates like They only measure themselves by use of feedback and a specific point and I think this is also maybe We are something that is counting intuitive. Not every customer feedback is the feedback that will drive you to the end result of the best product out there. There are many aspects to it. I can share just one example about us. We as in the beginning of the company, we for instance, didn't want to have a free trial and part of it is that we really wanted to hear feedback about a product only from people that the product means something to them.

58:29The best proxy for that is that they are paying because it means to get real value and in that sense it helps us. It helped us at the beginning to stay super focused about separating the wheat from the shaft in there with the customer's feedback. So I think it's a super important point and we need to take Customer feedback in context The other really interesting point here that you're making is this idea of we had I think I mentioned this already Ryan singers the creative the Smith that shape up Which is very centered around appetites over deadlines. There's so much like so many everyone listening to this has probably gone through an exercise We're like let's redo our landing page and it's like yeah, it'll probably have some impact Let's spend some time on this and ends up taking like six months and everyone's like Why did we spend six months redoing this friggin' landing page?

59:18Like, look, I would have given it three weeks and then moved on. And the only way to do that is you just commit upfront. We will spend three weeks on this. Well, do it as much done as we can in three weeks and then we'll move on. People talk about this very hard to actually do, so I love that's how you actually approach some of these bigger features you work on. Do you guys practice shape up by name chance? Or is this just like a thing you do? And no, actually, I wasn't okay. I know if it, but I definitely going to check it out. Okay, cool. Yeah, it's a whole method. And I think the episode right before this is actually that episode.

59:47Okay, let me go in a different direction and kind of keeps striking lessons from this journey because that was a really fruitful place to go. So let me ask you this question. What's one thing that you wish you'd known before stepping into the role you're in today? This is an interesting question. I think there are many aspects to it. And maybe if I'll take the personal aspect, so I've been in charge of the important and technology from like Sensei joined the company. But with that, my role has changed, I think like dozens of times. Like I feel I'm very fortunate to work in one company, but actually working dozens of different companies think about the scale that we talked about.

1:00:29Like each point is a different, it's actually a different company and a different role and different challenge. And I think that, you know, something that maybe is kind And the intuitive personally for me was that in many of the phases that we undergold with, I felt that what got me to this phase is not necessarily what's going to make me successful in the next phase. And if I want to be even more blunt, you know, there will like, personally, times when suddenly I saw how my biggest, you know, strength, for instance, like mastering all the details and having everything in my head knowing exactly what's happening on every corner of what we do.

1:01:15This was probably something that gave a lot of value when we were small. But as we got bigger, I think like it suddenly created, you know, even the damage, you know, continue to do the same thing. And in many ways, it takes time to do this realization and I think that a good advice that I would love to have is that don't be afraid again to let go or things that you think are superpowers many times you're superpowers that bought you to this point and made you successful many times you think that if you let it go you won't be successful and it's frightening but really feel that you need to constantly evaluate what your to control is actually what is the role and what is needed in order to be successful in it and not continue with the notion and this is something that I wish someone had done media.

1:02:16It took me time in many cases, you know, many cases that did it too late. Is there anything that helped you realize this or get good at this? Is it like coaching? Is it just doing it and surviving and failing and really, oh, I see. I think all of the above, I think that one sign for that for me was that in many cases I felt I'm doing a very good job, but then people like it can be like I'll give you an example, okay, like for instance doing a company like leadership QBRs, okay, quarterly business reviews. So when we just started it with it very early, you know, I would actually tell about everything.

1:03:03And you know, I remember one meeting that I went out of the meeting and I say, wow, I really managed to, you know, convey everything and explain everything and very like in a very articulated way. And like one of my colleagues in the college leadership team said, I didn't understand anything. What is the bottom line of all of this? And it was like, you suddenly realized that what you thought is good is not necessarily what other people needs from you at this point. And after understanding that, I went and asked, what would be beneficial for you? We said, listen, I want to keep in my head like the freeing in most meaningful things that you are currently in facing with.

1:03:53I don't want to hear everything and you know like it's hard but this was the point for me that I realized that I need to change and I need to change something and the requirements are different and like at the beginning you know I tried to say it but listen it's important that you know like you you're sticking to it, but we need to let it go sometimes and think from the beginning. There's this phrase that someone shared on this podcast once, where as you rise in your career, you often go from the person that is pitching leaders on something to the person being pitched, and that's a really weird place to move from, having to learn how to give great feedback, delegate, let go of things, and I love that this is a good example of that.

1:04:43But since we're getting a little vulnerable and open about stuff, I want to try this question. You've done a lot of podcasts and don't have interviews. You've been all over the place. Is there anything you haven't shared anywhere else that might be helpful to share here about the journey you've been on? Yeah, so maybe continuing with the same point, you know, like it's crazy, Johnny. And it's crazy personal, Johnny. If you think about it, like I remember, the way you once said, if someone would have interviewed me to a public company who I would say it has been in dollars in market cap and managing 2500 employees.

1:05:23I'm not sure that I would interview myself and get myself to the job. For me, there were a lot of moments and it's constantly happening. When things are going sideways and things don't work and you see so many things are breaking down and You know, you can be on the same day super happy and suddenly on the lowest point there is and I can show you know many times I have a I vest myself like whether I'm the right person to lead it whether we need like someone that is coming with all the experience to this phase And I remember like I talked to the air there with a run it tell me it told me something listen.

1:06:08First of all as the one who built it no one would be able to do it like you. And I think it's an important you know thing to remember when times are tough. I really believe that you know if you have the passion and if you have the will and if If you are willing to do the hard work in order to constantly adjust and evolve and to be vulnerable and also to say about yourself, I didn't understand something now, I need to learn it and I need to do things differently. It's a very important point if you want to do this kind of journey and it's hard. Something I can share, I can reassure everyone that are listening to us.

1:06:55you know, if you're feeling it, you're not the only one. Everyone are feeling it from once in a while. Be confident about yourself. Be vulnerable in order to learn and to evolve. And I really love to do like a mental, you know, mental exercise of like saying, like we said about the product. So let's say I'm, I'm a Daniel of like next six months. How do I want to look back on these six months? And what do I want to say about myself that I learned that I evolved? And this helped you get out from the state of like everything is okay. I'm good and it makes you like want to learn and want to evolve.

1:07:38And also like staying doing mode. Like I don't believe in like I think the one thing that really characterized me is that I can be very difficult and challenging time. But on the next day, I'm already bouncing back with energy and to come and do things and win it. And there are a lot of things that we as leaders need to do in order to help ourselves to keep this mental state. So I like to run. I like to do things that are unrelated to work in order to get back to my center, but then quickly bounce back and to really believe in myself in the team around me. So this is yeah, this is something maybe very personal, but I'm pretty sure I'm not the only one, you know, feeling it.

1:08:36I appreciate you sharing that. There's a post that I did a long time ago with a coach and she, it was a bad imposter syndrome and she made this really powerful point that like you are actually an imposter in the role you're in. You've never done this before. Like most people are imposter in the role. They've never been a cheap product officer in a lot of cases. They've never led teams this large. And first of all, I just realized that you actually are. And second of all, that's okay. And most people are like you sit. And then third of all, this advice you shared about it can work through that.

1:09:11It's really powerful. Just like, no money people feel this way. Work hard because a really important part of this, just like, no, there's another day and that you can bounce back. Remember that everyone, our people, no one is born to be like in the world that is currently at. And you know, another thing that, you know, in Monday, we are skating so fast. So even people that are coming with experience and I had, you know, the chance to see it over and over again. Because we're going so fast, each one of us will get to a point which is the first time he's doing it sooner or later. So experience matters and we have like a lot of people that are coming and bringing experience from from the outside but also remember that and remember that everyone of people and like no one was born in a position.

1:10:01Yeah, and the company's like yours. It's, I've, people have described it as like every six months, you have a new job. Exactly. Exactly. We had Cheryl Sandberg once did a talk that I was at where people are complaining. We're, we're just like so much just changing. We're growing every the culture is not as strong as it was. And there's just like things not working or processes or no, it was hiring is hard. And she's just like, this is the problems you want because you're growing very fast. And that's very good. Versus if you were not growing it'd be much more painful and hard. So be thankful to see the problems you're facing.

1:10:39I couldn't the game. You talked about things breaking along the way and things you have to deal with. Is there an example of something? I love these stories of just like maybe a moment of crisis along the journey where you thought like, okay, things are gonna fall apart. This is over. See you Yeah, to be honest, we have so many and like But again, this is the problems that you are lucky to have. But yeah, maybe I'll give you an example. Like, you know, I remember this day that someone from our customer success team is approaching me and say, listen, Daniel, we have a spike in performance issues in the board.

1:11:17And, you know, again, like our board is this table of like think about it like of data and on each time we add new functionality and we make the platform more mature people are taking it to the extreme. So if you look back eight years ago, so this kind of tables usually had like let's say five columns and 100 rows. And if you look about it today, it's like hundreds of columns, you know, tens of thousands and so flows and like, so performance was always a challenge and struggle like and making sure that everything works smoothly and this is also a value to us. We really believe that performance is the number one feature that makes people use your system.

1:12:01So you know, we came to me and I remember that like suddenly seen the spike in the tickets You know, it's super hard, right? Like you say, wow, it's something super hard. You don't necessarily have a magic wand of fixing it immediately. And what we did, we actually, again, connected everyone to it. The first thing I did was like taking this golf to everyone in the team, and showing and thinking together what we can do. And we did a lot of things and we walked really hard and we managed to make this situation better. And you know, and then time passed by and you were continuing and then it happened again.

1:12:45And I can share that on the first time, I said, okay, we're done. Like, we need to think totally different in a different way. And back in the days, this is where I think like many of our core, like long term projects have gone. The signature one would be Monday DB. It's like a name we use for like an underlying data infrastructure that we've been building in the last three years or so. So think about a very small team and a very small startup. I remember the day that we said listen. We need few of our most talented people. They are now not going to contribute features anymore. We are putting them on like a separate like place and let's think and solve this problem While thinking about 100x and you know we really like in many ways so different from what we talked about in so many other of the examples right and I think Now we said listen Instead of being like fixing an issue we want this to be our competitive edge.

1:14:01We have a very unique product architecture where everyone can build their own schemas of the table and you know, it's like a crazy thing in terms of technology behind it. We want to do something that will not only solve the problem, but also will serve us as a competitive edge. And we took a huge risk because you know, we took a lot of people and put them aside for that. Or like not a lot of people, but them very talented people. And I think in retrospect, by the way, we released Monday the day, I think, One and a half years ago, the first version, it did a huge change of customers. And in many ways, this is what actually makes us today a platform which is enterprise grade.

1:14:45So my lesson from that is that if you feel about something, it is strategic. You need to not only solve problems, but be super proactive. And also again, like this contradicts the fact of like, What are the goals? What are we going to achieve because you need to lean on something which is strategic. So with everything that we said at the beginning of the conversation, there is also things that you need to do because this is the company you want to build. This is the product that you want to build. And you don't necessarily get the look -sus of getting convictions from things that happen in the past or from data.

1:15:27You need to just go with your intuition and take this risk. And I'm super happy that we did it. Yeah. But this is an example where things really broke, you know, and what we did with it. There's a couple other stories of crisis I'm thinking back to and they're all seem to be a database started reaching capacity and we're about to fall apart because their growth was too fast. So it's an interesting lesson for people to hear just like try to anticipate this a little more. And it sounds like that's what you realize is like let's think 100x from now, not not just like a couple years from now. There's, it reminds me of, so Brian Johnson, he's this dude that's trying to live forever as long as he can.

1:16:07And he makes this really interesting point that I promise connects to what you're talking about, which is he's like, okay, what is your goal? He asked everyone, what's your life goal? And so they're like, oh, I want to do this and this and that. Okay. To accomplish that, the base goal you're not even thinking about is you need to not die. And that's actually the number one goal everyone should have. don't die. And I feel like that's infrastructure that companies is like, you have all these metrics and goals, but really the goal that underneath that as your infrastructure needs to scale. So it makes sense why this is outside of like, okay, we all these metrics and goals.

1:16:38Like not necessarily splitting it as a tax or as a risk, but rather like, you know, for our offering, like as a platform, this is like actually now one of our call advantages. So it's super important, as well that value to customers comes in different ways, shapes and forms and you need to to think about the experience and not only about like, you know, and many times the general experience start with things that are reliable, performance that you can count on them and suddenly you even use them differently because they are fast. So I think this is another important like aspect to it. That's such a good point.

1:17:17When you have a problem, some that's slowing you down or might crumble the company, just not flipping it from. How do we just put the bandaid here? It's how do we turn this into a strategic advantage if we really invest the time? I like that a lot. Okay. To start to close out our conversation, I'm going to take us to AI corner, which is a recurring segment I tried to get to is more and more with this podcast. And the question is, what's an example of using AI tools in your day to day work? To do better work, to do faster work that you think might be helpful to other folks? Maybe I start with a personal one, you know?

1:17:52Like, it's not about work, but I think it really shows that for me it was like a moment of like really saying this has so much potential in it. So I actually prepared myself for a marathon and unfortunately I got injured in my knee. So yeah, so I went to do an MRI scan and I finished the scan and they gave me this disc which the results and then they said listen You need to schedule a doctor appointment. It's five days from now Okay, I said I took it put it in charge of it in ask for like the results and Explanation of flying by line. What what does it mean? And then I of course went to the doctor and said this are the results, but I think like for me, you know this is something that I was really happy about using it.

1:18:48And it also opens my mind a lot because I think that if you think about it from the product perspective and this is how we think about AI in Monday, the technology is amazing. You can just so much with it, but there's still the part of like productizing it because every person that I talked with him about this example like with enthusiasm, he said, How did you think about putting your MRI? And I said, I don't know, like I just did, but this is all like creating products that actually allow people to leverage this technology. And more on the work side, you know, I use it a lot. I think like for me, like one recent example, I would say is like we really worked hard towards like determining the pricing for AI offering and that I was mentioning earlier.

1:19:41And just in like two hours, I managed to get a full perspective on what everyone else are doing. You know, and we have analysts and we have product managers, but the fact that I was independent and managed to get like, you know, the initial thoughts and like all the information in just a bit, it was mind blowing. So I use it a lot in order to understand Things that are like very extensive like what the competitors are doing What is the history of this and that and I think it helped me a lot in that sense These are awesome examples and is this all chat GPT? Is that the tool choice and You know, it's hard.

1:20:23We I have like my own periods right now. It's changing from one week to another This do actually with chat GPT. Yeah Very cool. The first example of my wife does all the time, my mother -in -law was in hospital and we're waiting for the doctor to show up and she just put the chart in chat GBT and it's like what's with the problem and it's exactly what he told us. And it feels like like it feels like we're in a world now we're an engineer without say cursor or one of these tools is just not like that's not that's not possible anymore. And it feels like now we're going to doctors is like if you don't do this and see what it says like you're missing out on a big gap.

1:21:01There's this New York time story, I don't know if you've seen where they actually compared a doctor's analysis versus a doctor plus JGPT, plus just JGPT. And guess what was the best, most accurate diagnosis? Yeah, I want to say JGPT, you know, but then... That's exactly who it was, not even a doctor with JGPT. You know, I tell you, I tell you story about it. And so in the MRI, I did it because I wanted to go skiing and I didn't know if I can do it or not. So I had shared GPD and he said like all the recommendations and what I need to do and so on. And then when I was at the doctor, I said, I asked him the same question.

1:21:43Can I do ski? He said, I don't know, I never ski. You know, so it's not only about like getting the information straight away and getting accuracy. It's the fact that you can continue deep dive with it. And this is something that also like when I was in the pricing, you know, it's not only the bit of information, but the fact that you can continue and continue and continue and continue. It's like it's definitely super super impressive. And it doesn't get annoyed. It doesn't get bored. It's in its very supportive. Always with good intent or not. But yeah. So kind, amazing. Okay, well Daniel, we've covered a lot of ground.

1:22:17This was extremely fun. Before we get to our very exciting lighting round, is there anything else that you wanted to share or any other nuggets of wisdom you want to leave listeners with? I think that in many ways, like the things that we manage to achieve in Monday is due to the great people and culture that we have. And you know, on early days, we used to take it for granted in a way that not the people but the culture, the fact that everyone understands it, the fact that everyone are practicing it and then you say, okay, culture is like something that you can put your fingers on. But now as we scale, like, I really see how this is what actually drives everything forward.

1:22:59So maybe just to say like on a personal note that a huge part of how I see my role is about like the people and also about how we walk together and what kind of an environment we want to build to ourselves. And we talked a lot about it during the episode, but you know, I really feel that I can't underestimate on how meaningful it is and how like grateful I am that I'm working with such talented people and doing what I love. That's awesome. I bet we could do a whole other episode on just culture and what you've learned. Building a culture with the culture is like at Monday, but we got to get to our very exciting lightning round.

1:23:40Daniel, are you ready? I'm ready. All right. So I've got five questions for you. First question is, what are two or three books that you find yourself recommending most to other people? The first one I would say is like, is there no wools or a book by Netflix? back in the days we used even the slides, but I think we took a lot of inspiration out of it and I think that although we have different cultures many of the things around like, you know execution and like excellent people and so on things that like I can really resonate with and this is something that we really like to give people away after talking about our culture and so on to get inspiration also from other cultures and And another, maybe on a different way, you know, aspect is about that actually Roy, our course he always giving to me, its name is nonviolet communication.

1:24:42And it's about effective ways of communication and understanding the people and their needs and how to communicate in a way that actually promotes an effective communication. And what I liked about this book is, you know, mainly we love to talk a lot. And like, after we both read the book, like, our way of talking like changed, so it's very practical. So I also like to give it a way to our leadership and people within the team because I think it has like little value in it. I'm trying to remember the framework of non -violent communication is like I observed you that speaking too much in this meeting and that made me feel like I wasn't listened to something like that right?

1:25:27I forget. You shouldn't be judgmental. You just need to say facts and talk about how you feel like in that. Yeah. And I know I'm kind of joking about it, but it's actually really powerful. And we had Carol Robin on the podcast who created this program at Stanford called Tachy which is similar to this whole process, this whole approach to talking. And by the way, I love the combination of Israeli directness and nonviolent communication. I want to see that in action. Yeah, definitely. Okay, next question. Do you have a favorite recent movie or TV show that you really enjoyed? So to be honest, I don't watch TV so much.

1:26:06Like I get bored really fast and going back to other things. but when I do watch TV, so many times it's like in order to clear my head, so it's not that kind of exciting things. Maybe a different thing that I'm doing is playing on the PlayStation with my son, you know, FIFA, just to vent out. And in terms of serious, maybe like one thing that pops up is like the formula. I really liked it. Formula one. In Flair. Drive to survive. Drive to survive. Exactly. I really love seeing the dynamics and everything behind you know, it looks like something simple of like driving cars, but you see that there's so much into it.

1:26:52And so it's also something that like really interesting and like opens your mind to watch. Yeah, I haven't started the new season yet. I wonder if it's great. Yeah, likewise. Okay, next question. Give a favorite product you recently discovered that you really love. So, you know, I don't want to like to fall into the all the eye -trap, you know, in terms of products. So maybe I'll say something which is not so recent, but the product that I love. And I really like to take pictures. And one product that I really love is Google Photos. I think that, you know, they manage to create something which takes like the technology edge, but to a place where myself as a human like really can connect to it and get a lot of value for it.

1:27:43So I'm like a really heavy user of that. Yeah, that is a magical product that I think people under, under appreciate. Yeah. Next question, Diva, favorite life motto that you often come back to find useful and work your own life. Stay positive. Like I think being positive, saying, saying like the good things is the huge huge power and it's a huge driver and it allows you to to give energy to the people around you and it contagious. So I really love, you know, staying positive, making sure that we keep being optimistic and it doesn't mean that you need to let go of the problems and don't see the problems but also think about always look forward and always think how you can take the current situation and make it better and I learned with the way that it's really more fun and actually brings better results this way.

1:28:44And 1 ,000 % aligned with that. Final question, I know you were in the army at one point in your life. Is there anything that you learned from that experience that helps you build better products? The funny thing is that I think that like many things that I did in the army, I was actually commanding of like a very big group of people in the army. And I think it's not about building products, but more about building teams and building like this sense of purpose, sense of shared, like belonging. And I think that in that way many things are quite similar to be, it might be like counter -intuitive, but many things are quite similar.

1:29:31And from that many of the things of being together, although it's like an hierarchical environment, it's something that I take with me, and a lot of like practical ways to lead the bigger organization, I would say. Daniel, this was awesome. You're awesome. So much stuff that we went through so many golden nuggets. I think they were going to help a lot of people with building products, building teams, scaling, surviving all these scaling challenges that keep coming up in these conversations. Two final questions. Working folks find you online if they want to reach out, maybe talk about being more transparent.

1:30:05And then how can listeners be useful to you? So online, I think that too many ways is like bilingual. I would say, and second is podcasts. And I'm guessing in a lot of podcasts, and I think that this is a cool way to share things. For stories and for practical examples. And in terms of listeners being useful to me, So first of all that they in many ways they are already Are useful to me. I really love your podcast and like I'm ganging a lot of you know insights from others and this is something I really love. So many of the people that probably listening will also contributing to that so thank you for that.

1:30:50And I really hope with that that this episode would also be meaningful to people and that they will take value out of it. And if they are it would be amazing to hear about it. like I remember, you know, someone that sent me a picture of his new dashboard in the office and what he did with that and had like additional ideas of what you can do that we actually took also here in Monday. So if you do something even if it's small, let me know. It's super fun to hear and also interest things. All right, there's the call to action. If you implement some a Danil's advice, especially put up new dashboards or monitors in your office, please send photos of her LinkedIn.

1:31:32It sounds like it's the best medium. Danil, thank you so much for being here. Thank you very much, Danil. It was a pleasure. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or a leaving review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny'sPotcast .com. See you in the next episode.

From the publisher

Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide.

What you’ll learn:

1. How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their team

2. How sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignment

3. How focusing on impact, rather than just shipping features, has transformed the company’s culture

4. The story behind monday.com’s decision to launch five new products simultaneously and how it redefined their market positioning

5. How they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver faster

6. Daniel’s personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective

—

Brought to you by:

• Enterpret—Transform customer feedback into product growth

• Airtable ProductCentral—Launch to new heights with a unified system for product development

• Vanta—Automate compliance. Simplify security

—

Where to find Daniel Lereya:

• LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/

—

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

—

In this episode, we cover:

(00:00) Introduction to Daniel and monday.com

(04:20) The pivotal moment: competitors shipping faster

(08:50) Setting ambitious goals

(17:44) Focusing on impact rather than features

(27:07) Transforming your product quarterly

(32:07) Scaling monday.com: challenges and strategies

(39:14) How monday.com maintains transparency as a public company

(45:40) The importance of taking risks

(51:02) Counterintuitive lessons in product development

(54:33) The value of timeboxing and deadlines

(57:28) Embracing user feedback

(59:54) Adapting leadership styles

(01:04:43) Personal reflections on leadership

(01:10:41) Handling crises and strategic planning

(01:17:28) The role of AI in work and personal life

(01:22:13) Final thoughts and lightning round

—

Referenced:

• Monday.com: https://monday.com/

• The basics of a monday.com board: https://support.monday.com/hc/en-us/articles/115005317249-The-basics-of-a-board

• Eran Zinman on LinkedIn: https://www.linkedin.com/in/eranzinman/

• Roy Mann on LinkedIn: https://www.linkedin.com/in/manroy/

• Tal Harari on LinkedIn: https://www.linkedin.com/in/tal-harari-a2515215/

• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile

• A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals): https://www.lennysnewsletter.com/p/shape-up-ryan-singer

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• AI blocks: https://support.monday.com/hc/en-us/articles/18433811274386-AI-Automation-blocks

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox

• SpaceX: https://www.spacex.com/

• Why and how to lead with transparency: https://monday.com/blog/monday-insights/may-30th/

• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra

• This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your data scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/

• ChatGPT: https://chatgpt.com/

• Cursor: https://www.cursor.com/

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• FIFA 22: https://store.playstation.com/en-us/concept/10002538/

• Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890

• Google Photos: https://photos.google.com/

—

Recommended books:

• Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp.com/shapeup

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860

• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X/

—

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

—

Lenny may be an investor in the companies discussed.



This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

More from Lenny's Podcast: Product | Career | Growth

All 287 episodes
Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARRLenny's Podcast: Product | Career | Growth · 1 h 32 min
Listen in VO