20VC: Why Hiring in Tech is Broken and Founders Need to be as Good at Firing as they are Hiring, Why Product Differentiation is Unsustainable & Why the Current Generation of Tech Employees are Entitled and What Needs to Change with Jean-Denis Greze @ Plai

21 Jul 2023 · 50 min

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In short

Podcast Summary: The Twenty Minute VC (20VC) Episode with Jean-Denis Greze

Episode Overview

  • Title: 20VC: Why Hiring in Tech is Broken and Founders Need to be as Good at Firing as they are Hiring, Why Product Differentiation is Unsustainable & Why the Current Generation of Tech Employees are Entitled and What Needs to Change with Jean-Denis Greze @ Plai
  • Guest: Jean-Denis Greze, Chief Technology Officer at Plaid and former Director of Engineering at Dropbox.
  • Host: Harry Stebbings
  • Key Topics: Hiring practices in tech, product differentiation, remote work culture, and the evolving mindset of tech employees.

Key Discussions

  1. The Journey to One of the Most Powerful CTOs
  2. Career Path: Jean-Denis shares his journey starting from Dropbox, which he considers his major career break, leading to his role at Plaid.
  3. Analyzing Talent: He discusses how he evaluates LinkedIn profiles, emphasizing the importance of stability and project engagement over job-hopping.
  1. Hiring the Best: 101
  2. Lessons on Hiring:
  3. Importance of defining the job role clearly to avoid mismatches.
  4. Reflection on hiring mistakes, including the need for alignment in interview panels.
  5. Firing as a Skill:
  6. Jean-Denis stresses that founders need to be adept at letting go of talent that does not fit the evolving company needs.
  7. The discussion highlights the pitfalls of retaining underperformers too long.
  1. Product Differentiation is Not Sustainable
  2. Critique of Product Differentiation:
  3. Jean-Denis argues that product differentiation, especially through user experience (UX), is becoming less sustainable as it can be easily copied.
  4. He cites Salesforce and Snowflake as examples of companies that might not maintain their market positions due to shifting market dynamics.
  5. Mistakes in Product Market Fit:
  6. Founders often misjudge the stages of product market fit, leading to miscalculations in market expectations and growth strategies.
  1. Remote Work, Titles, and Employee Mindset
  2. Work Culture:
  3. Jean-Denis suggests that tech employees often view their employers similarly to how citizens view their governments, indicating a sense of entitlement.
  4. He reflects on how remote work affects productivity and company culture, noting that while remote work may benefit some, it can hinder collaboration and creativity.
  5. Title Importance:
  6. He believes that while titles may not matter in small teams, they become significant as organizations grow, especially for recruiting talent from larger companies.

Key Takeaways

  • Firing is Essential: Founders must recognize when to fire employees to maintain a healthy business.
  • Realistic Hiring: Hiring should focus on immediate needs rather than long-term scalability, especially in the early stages of a startup.
  • Market Dynamics: Current economic conditions may reshape how tech companies view product value and market fit.
  • Evolving Employee Expectations: The mindset of tech employees is changing, with a focus on work-life balance but potentially at the expense of high performance and dedication.

Conclusion Jean-Denis Greze offers a candid examination of the challenges facing tech leaders today, from hiring and firing practices to the sustainability of product differentiation. His insights reflect a deep understanding of the shifting landscape of the tech industry, emphasizing the importance of adaptability and honest communication within organizations.

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Additional Resources

  • For more information on this episode and additional resources, visit [20VC Website](https://www.20vc.com).

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Transcript

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0:00I feel that the relationship of many tech employees with a tech employer is the same as like a French citizen to the French government. Somewhere between 15 and 30 people, things will break on the management side. First time founders they don't realise they have to be greed at firing. I mean, wow, this is one broad ranging discussion. Welcome back to 20VC with me Harry Stabbing's and say we're joined by one of the best CTOs in the business, Jean -Denny, CTO at Plad. Prior to joining Plad, Jean -Denny was director of engineering at Dropbox and he's also a prolific angel investor. than the incredible portfolio including the lights of Nax Health, Merge and Ruper Health to name a few.

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3:15I'm so excited for this, I have many good things before we started the conversation, so thank you so much for joining me stay first. Thank you, Eric, I'm super excited to be here, I feel like I'm getting the benefit of being on here more than you're getting the benefit of having me on the show, but I'm excited to do my best to impress. Well, I'm about to extract a decade of knowledge, so I think I'm the one winning, but I want to start with your career. And I think careers are often made actually with more singular moments. So when you reflect what you say was the single biggest break in your career, and how did it impact your trajectory?

3:45It's a good question. The answer would have to be joining Plaid as to lead engineering. I joined when the company had 40 -ish people and less than 10 million in ARR. We've had crazy trajectory. And it means in terms of my career and my ability to be successful long -term, I have a lot of options now that I'd never would have had if I hadn't joined Plaid. Joining Plaid is not what I consider the lucky break that I had. That would be joining Dropbox, which is my first job, like Troulee and Silicon Valley. So before Dropbox, I kind of had a weird career. I worked in tech for a bit. Then I'd been a lawyer for a bit.

4:19Then I'd helped a friend kind of grow a company, like a FinTech company in New York, but more on the hedge front side of things. And I hadn't had like what you would call like a AAA employer on my resume. I was smart, but weird outsider with a little bit of an attitude. I realized at some point that if you want to be an engineer and you want to do great engineering work, at the time at least I felt like you had to move to Silicon Valley. And I was in my early 30s, you know, I don't think I'd had a great success and I knew a friend a draw box and so he got me in the pipeline to apply. And you know, I applied there, I know because they told me after the fact I actually didn't do that well in the interviews.

4:53I did well on half of the interviews and I didn't do well on the other half of the interviews, especially on some of the like the people skills and I think I came across as it'll too smug and sure of myself. And there's two people at Dropbox that saw something in me during the interview process. And they were like, look, no list. I was like, we should hire this guy. He's got some spikes, like he's weird, but that's what we need at the company. Dropbox is very good, not just at getting the standard talent, but at looking at people that weren't quite conventional that they thought could really accelerate the business.

5:21People don't realize now maybe that Dropbox, like 2010 to 2017 on your resume, that really just opened all the doors. or a JD, you were a talent, but your CV did not show it at the time. My question to you is, when you look at LinkedIn profiles today, what makes you excited? So for me, duration makes me excited. I hate bounces, this is what I call it, where they've done a year, a year, a year, 12 months, 18 months, 12 months. I like 10 years, duration. What makes you think high quality when you see a CV or a career? It's a really tough question, and I think already in an interview process, you're trying to recap someone's talent in four to five hours.

5:59For me, there's a ton of red flags staying too long in level, like not having a good trajectory. Jumping around from company to company, you can jump around once or twice. If you do it over and over again and you never find a place where you're able to like, really hit that velocity, that really bothers me. I look at online things that you've built. So frankly, like your GitHub, the projects that you've shipped, maybe even your blog, I think that stuff can get me excited. But what I want quickly is interaction with, you know, the interviewing team. What I want is like time in a room with you. The resume screen for me is fairly limited.

6:32You have to always ask the question with talent. Are they the right person for my business? Not are they a great person, right? And I think there's a big delta here. Like I always give this advice to startups. They all, you know, startups, they're like, oh, I want the best engineers. And I'm like, you're building a crud app. What is the best engineer for a crud app? The best engineer might be the person who's like graded react or graded rails or whatever. They don't have to know distributed systems, they don't have to like know all that called test technology. So let's look for someone who's got an amazing track record of like the kind of front end work that you have or the kind of full stack work that you have.

7:08And when you do that, it's no longer like a grade resume. It's like your things you're looking for and you ask yourself does the experience on this resume seem to match what I'm looking for. And I think that's how you find quote unquote great for your business. How do you advise founders in terms of hiring ahead of time? You spoke about the best engineer that for your business. Often VCs are claimed to be able to show the problems before they become problems and help you hire ahead of time. Do you think founders should hire ahead of time or aren't you it's hiring for the here and now? I think I've changed my mind on that.

7:39I think for ICs, very early on, like first like 15 people, you want to hire for the here and then now you want people who are hungry who can solve the problems you have right right now because you're trying to get and expand the amount of product market said that you have in the amount of product momentum. At most companies, the advice that I gave is somewhere between 15 and 30 people, things will break on the management side and the problems that you encounter are not cutting cutter. You can't ask someone who's grown a company to 200 and ask him give you a roadmap of the changes they had to make and be like, those are the changes I'm going to have to make.

8:11No, because every business pretty quickly ends up looking different. So at that point, what I generally say is like, Okay, you need to hire your first few managers and your fur head of. Like the first person who's gonna grow your product team or grow your engineering team. And I think there, your two choices you can make. One, you can hire what I call the four year candidate, the person who's run like a 75 to 100 person team. So they're gonna come in at 20 and you're gonna be as a founder, you're gonna be like, well, this person is gonna be able to grow us for a while. They're smart, they're problem solver, they'll get in front of it.

8:38Or you can hire what I call the two year candidate, maybe your person that's managed a 35 to 40 person team, much easier hire, but that person, at least you know, like, hey, listen, like they're going to be able to get the next year to have two years. They're going to be great. And then I'll have to reevaluate. So I used to be in the four year camp, but it's just such a hard hire. And there's actually this thing that happened where the person who's really a really large team may once upon a time have been good at running a small team, but they may not be anymore. I don't think I would be a good manager for a 20 person team anymore.

9:05I was when I joined plaid. That was six and a half years ago. Like I've lost all those muscles. And so if you go too long term, if you don't hire for the here now, sometimes you get someone who's not that excited about the here and now, not willing to roll their sleeves back, maybe even their technology understanding is behind where it needs to be. Things are changing on the ground, so I think it's always easier, faster to make the shorter term higher, get the impact, as long as you're honest with yourself when they stop scaling. Right? And so you, the recognizer, still scaling, I'm going to support to mentor them, get them to the next stage, or you're like, hey, maybe it's not quite working out, I need to think about every two to three years upgrading my exact bench.

9:41We always say about stop scaling and it's like romcoms, it ends there. What happens when they stop scaling? Do they move on? Do they remain in the organ we layer them? How do you think about efficient handling of that? With those categorized characters? Yeah, I mean, how unfrenched can I be on the podcast? Look, it's capitalism and your responsibility is to share holders, right? You can do right by people and the transitions, but you know, sometimes you get someone who realizes that they need a better leader that they're gonna learn from a better leader above them and they're ready for it. And sometimes for everybody, it makes sense for them to just go find another gig with, they've grown at your company and they can now do another stage, it's not the stage that you have.

10:21And it's okay. I think as adults, you can have these conversations. I think where you get in rough waters is when you don't give the person a chance. I call that like putting the person in a box where you have this image of them from when they joined and the company hit some kind of rough patch and you don't give them some chance. I'd like seeing if they can go out of it. I think the human thing to do is to give him the chance, but you're a founder and you've hired all these other people and if Wonder if function leads isn't scaling yeah, you might give them three months, but pretty quickly you got to realize Hey, it's not working because next thing you know you might have you know if you wait like a 12 months and then you make a new hire and that person on ramps Next thing you know you've wasted 18 months of potential momentum at your company and that's dangerous And I think this is like not a super podcast like happy happy makes me look great kind of statement and but there's great hiring and there's great firing.

11:06One of the things you realize about founders is, first time founders, they don't realize they have to be great at firing, they just think they have to be great at hiring, but you have to be great at realizing when your talent's not working out and identifying that and working with them and moving on. And initially founders don't do it early enough and then they learn their lesson a few times and then get really good at it. By the way, it's really interesting that people think about, like, oh, it doesn't sound good on a podcast. What founders love the most and what makes them like people the most is actually the honesty.

11:33The naught BS, selling your company, you know, it's all about mission and vision. That doesn't sell. I made people dislike you. What does being good at firing mean? And how can I get good at it? It's like having a breakup. I don't think you truly get good at it. And I don't think you ever have a playbook where both sides come out of it, like super happy humans. That's the reality. So the first thing you got to realize that. What I say good at, I actually don't mean the conversation with the other person. I mean, identifying at the right point in your company, that the odds of success of that individual and the role is no longer right for the business.

12:05If you can look at someone in the eye and you're convinced yourself that it just doesn't make sense for the business, you've given a shot for them to improve and prove themselves and they haven't, you're just doing what's right for the business and they will understand that and they will respect you for it even if they don't like you in the moment and they don't feel like it's fair. I just think that's how you have to treat it, right? There's a human level, you know, how you deliver it, how open you're in communication that those things matter, but at the end of the day, it's about what's doing right for the business.

12:32Probably the biggest mistake is not giving feedback. Oh, that is no, no, no, I disagree with you. Don't give feedback. That's a terrible thing, JD, because that always all give you with your feedback. I mean, before, it shouldn't come out of left field. The person should know that their performance is not quite meeting the bar that you have anymore, a couple of months before. Saying your head, you're just like, ah, it's not working out, it's not working out, it's not working out, and then you show up in one -on -ones and you're like, hi -five, let's go watch, like a soccer game, you the best. You know, then when you deliver the news, that's just not that's not going to feel good.

13:02Yeah, in the moment, no, you've made the decision. There's no argument, right? If you've made the decision, you know, they try to argue with you, like, look, listen, like, I'm doing what I think is right for the business. This is my role to do what's right for the business I've thought about it. This is this is what we're doing. I'd like to work with you on like a transition plan that works when when you reflect on hiring, what's been your biggest mistakes? The first one's not being crisp about what we need in the role. You know, it's the difference between I need someone to run data science are major data science initiatives around risk and fraud.

13:31I'm really going to value somebody who's done that in industry for a bit, but I want an out -of -the -box thinker because at plaid we're not doing fraud and risk like every other bank. That second thesis like calls the space significantly. It's like okay they've got to have work at a traditional institution but then I've got to have seen them work in a really creative environment. It's fraud at risk so I'm not going to hire a data science person who's not had any of that experience. You really got to get the requirements really Chris first. Second is your interview panel needs to be aligned on what you're looking for.

14:03I've seen too often especially with senior hires. All the interviewers are like you know heads of things and they're all asking the generic question like oh tell me a great success in your career. Tell me about a time you failed. You don't get real signal from that like you need to be like hey head of age are I need you to talk about how they can have the work teams through difficult execution challenges. Hey like GTM person like I really care about can they work with PMMs on pulling out data requirements for data products. Like make it, make the interviews really specific. And then number three, you have to have interviewed enough people that you know what grade looks like.

14:35If you have the perfect candidate be your first hire, like the first person you interview, it's really hard to pull the trigger. People don't have any comparison points. But if people have, if that panel has seen seven or eight candidates before and they'll have a feel for what good is and what grade is. And so this sounds unfair again, but you kind of need to put the interview process through rounds. And so what you do is if you have your first grade candidate and they come really early, at that point in time you got to interview three or four other people. You got to find three other four people to interview because you want your panel to feel confidence that someone truly is great, otherwise it's hard to pull the trigger.

15:09And then everything else is on the recognizing if they're successful, setting them up to succeed. Having an objective data point pretty early on, you've got to have like a reminder in your count or three months and four months and five months and whatever, that were you objectively sit down and you're like, ask them to do these things, are these things done? I thought this would change the trajectory of this function, is the trajectory changed? And if you can't answer yes to the questions, then we may be into the conversation you're not just finished having. I love doing one idea because I just write these casuals and the fuck, Ram, I'm so enjoying this.

15:38As I have two questions I thought on the negotiation pre -joining side, one of my biggest lessons is when people are really difficult on the title. I want chief of staff not EA. I want head of engineering not VP of engineering or whatever that is. It's never a good hire. Do you agree? And have you felt the same or aren't she in my wrong? Certainly the most of the environment environments I've worked in, we try to be kind of low ego low title. We want the best ideas to win not just the most seniority. So even at Plaid amongst ICs for example, there are no titles even in managers outside of the person who leads like a giant area, we don't have directors and things like that.

16:18So I've been very much in need, like it's not a red flag, but it's a little bit of yellow flag when people really care about those things. The flip side of it, which I think is it matters in the industry and you can never fully divorce yourself from the industry, especially when you get to a certain size. When you get to like a thousand people, two thousand people, you're going to recruit people who have titles, you're going to recruit people from whom titles matter. So like a like a thing for you is there's bias and unfairness in the industry. And so there's some underrepresented groups for which being a staff engineer on LinkedIn is truly meaningful career wise.

16:52It's not about ego, right? It's about this feeling that the industry hasn't done right by you and when you achieve this thing that is truly meaningful, you want to celebrate it. So I think at scale at our size right now, like we're a thousand people total, I think you want to go with the grain of the industry, not against it because it's just too much fighting to go against it in some places. You have to be picky around where going against the grain really accelerates the business versus the places where you should just be more default. I think when you're very small, it is a red flag. People should care about impact.

17:22Everything's going to be fluid. What is going against the grain to accelerate the business? Very rarely. My overarching thesis is that a lot of people things. How you level, how you title, how you comp, How you organize your org, like your manager to IC ratio, remote hybrid, pick a thing, pick one of the three options on the menu for each of those. And just like move forward with your life, I just don't think it's the difference to you know, good and a great business. Bad strategy, bad product plan, going through wrong market, the efficiency gain or loss is like 100 % or 0%. You know, you build the wrong product, you're slightly better at leveling people like, I just don't think that fundamentally matters.

18:03How much does speed of execution matter? That's the most important thing. It's shots on goal, right? You execute faster, you get more shots on goal, it gets your competition. You want to be the fastest person. You mentioned some crucial, crucial topics there. One of them which I'm actually very passionate about and not in a friendly way either. But it's the in -person versus remote versus hybrid. Talk to me about how you think about this and do we have an opinion here? One opinion I have is we've talked too much about it. When I say it doesn't matter, I think they're probably really successful companies before the pandemic that were really going hard after fully remote first.

18:39It worked for them because they had the people who went to work there were people who want remote first. What happened in the pandemic as we forced people into working models that maybe they didn't like? So on my team, I have people who like remote first and I have people who want to be in the office because I didn't pre -stallact in my hiring criteria like a specific persona. Now, you can't make a decision. I don't think it doesn't matter, but again, I don't think it's the difference between success and failure. You make a decision, you make sure you're hiring and your culture matches the decisions.

19:05There's a few areas where I think you should be careful. So I'll give you an example. Highly creative, fast -moving work where you're not sure what their requirements are, and where your customers are local, meaning where you can go and talk to your customers by like walking over to their office. I think in person is better, because I think you collaborate more effectively. It's easier to get everyone on the same page. you can go talk to customers by like, you know, taking a car, walking over. And so if you have a lot of work like that at your company or you have teams that look like that, I think getting those teams to operate in person is beneficial.

19:37However, at scale, incremental improvements to existing products, where you care about efficiency of the team and you have clarity of roadmap, personally, I think almost in remote were more effective. I think the only thing in remote that's hurting me is Paul Skore in terms of belonging and how much fun people are having on the work, like I think that has gone down from before, but I think it's in terms of the quality of the work and the productivity it's the same. I totally disagree. They do not work as hard and they do not work as well, and they do not feel the same culture togetherness. The idea sharing is totally different.

20:11Whether you're in marketing, whether you're in sales and the camaraderie, your attention is slammed. Do you have a bad day? You go down to your other half and they say, oh darling, well what about those LinkedIn recruiters who are offering you jobs at the same pay? Versus when we're in the office together and you and me go out for a drink at the end of the day And you say dude, I love working with you and I go, ah, you know what? JD's good and plads a good place to be and so I think it fundamentally changes the creativity and retention Fabric of a company and I think we're gonna see a load of sorry I'm on my high horse we see a load of VNCs who made a load of investments without ever meeting the company And they are unraveling faster than ever now and that is in large part because they didn't spend the time in person I think I agree with you on the culture side, there's hybrid models where you come in like two to three days a week and you make the office awesome for those days where you can get a lot of the benefits that you're talking about.

21:00I disagree on the productivity front. We've had a lot of success there, but you look at all the early stage company like a lot of them are going back to in person. It is happening right now. There's an exodus from New York to SF. That's happening and from, I'm not saying Miami, but from other places where people went and it's around AI because the zeitgeist is here. All the AI folks are getting together in the evenings are going to the same place. Like all the Gen AI stuff, it's sucking a lot of people back to... You have to be in the valley to be doing AI startups today. So I was in Europe for a trip like a few months ago, and I think what was really fascinating to me is how much of the culture of how you build the company and scale a company is now internationalized.

21:39Ten years ago, there was this knowledge about like, what does your first PMM do? And like, what's growth hacking or PLG? And how does it... Now, kind of everyone knows that stuff, it's pretty impressive. I think there's still more people who've seen through it here, who've done it like four times, but there are a lot of other places in the world that have proven that they can export the company, the startup building, and the culture of Silicon Valley. The air stuff you can feel right now that the side gassed is NSF, but I think it's still an advantage to be here. I do wanna see it. A lot of people who love remote and hybrid, I think love it because there's a lot of life balance that it brings.

22:15You've said before what life balance is good for people who do not care about what life balance. Can you help me understand this JD? You mentioned earlier that you've made a lot of investments in France, right? I'm gonna say some things that people are gonna like probably on the podcast, but maybe my team won't like it at all. I don't think my team is this way. But France is interesting, right? Because as a country, there's kind of this ethos. It's not cool to talk about work and you don't want to work too hard. You work to live. That's like the Frenchness. And the result of that is if you are a person willing to work 80 hours a week in France.

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22:50If you try to work for a big company, you get hammered down. They like, you don't let you work that hard. Like, you know, people like you're making us look bad. Like, they like, won't let you use your workstation off hours. Like, it'll be weird. But if you're a startup or if you're doing something new or you're like an independent, you have your own little company like a law firm or a small investment bank, you can crush it because your competition's working 40 hours a week and they're going on vacation all of August. And so if you're the law firm who's willing to be available from July 15th to September 15th, like, welcome.

23:20People will go and work with you. The way I would talk about tech is, you know, tech 20 years ago, it really truly was tech -broy in the sense like everyone was in the early 20s. Everyone was working all the time. There was no work -life balance. And as tech grew and had a lot of success, there was this movement around like, hey, if people with kids want to be successful here, people from different walks of life, like we want to create an environment where you know you can work 40 hours and still do great work and have a great room in relation. And that's what's happened, right? Like people have fought these battles and the culture has changed.

23:50But the culture has changed so much that now I have people who want to work hard, who are like the French person at the big company. They're like it's hard to work hard and I feel guilty doing it and all these things. And what I always tell them is like you're thinking about it wrong. It is much easier for you to get a promo. It is much easier for you to look good if you're willing to do those things because the average now is truly going into this like you know 40 hour week kind of thing. And I feel that the relationship of many tech employees to their tech employer is the same as like a French citizen to the French government.

24:19The employer shall provide all the big problems in life or the fault of the employer like kind of this weird like lack of ownership mentality. It has the entitlement in it for sure. Overall and why I think innovators and small companies will continue to have advantage is because I do think if you care more and you're more focused and you're willing to go the extra mile, you will build better things. And can't ask everyone to do that. So I like the fact that we have work -life balance. But I think for the people who really like want to push, they'll have more career success. And one of the situations that I find always interesting are new grad hires across the industry.

24:52Really, these brilliant, brilliant people, right? And who join the tech companies. And the first time in their life when there's not equal treatment is the first promo cycle at their company. When some people get promo to the next level after 12 months, some it's 18 months, some it's 24 months, some it's 30 months, and it happens and they're like, but I'm as smart as the other people. And then suddenly it's like, no one cares that you're a smart, but people care about is, are you a top producer? And there's different ways you can be a top producer, but when everyone's as smart as you are, what's going to differentiate your success?

25:23And I think hard work will matter now. You can't be surprised when someone outperforms. Do you know what separates the one that does get the promo than the one that doesn't most often and this is not me being an old man boomer It's one who's in the office more as well So you are you're back to it. I totally agree. I do want to ask one final one on people And it's just a question around do you believe that you can be truly great and have work life balance? And when I say truly great let me put a placement around it build a ten -billion dollar plus company So I know a few truly great people who have the right view point and are really good at motivating and delegating.

26:01They create the structure for success like the North Star, the product roadmap. They're able to motivate other people to go in that direction. That person can do it and that person could be a great CEO. It's possible. But as a whole, no, you need to do great things. There's a great sacrifice. You'll find exceptions like one -offs, but I think on average it doesn't play out. And the analogy that I would say is to like a professional athlete, a LeBron James or what not. There's plenty of people who are professional athletes who from a pure physical understanding of the game they're there and who just don't put in the work and there's people who put in the work.

26:35With athletes, we're totally okay to make fun of the ones that don't put in the work. The sports writers like make fun of them all the time. They're like, ah, it's a 15 year career. You get one shot of this, like you get your big payday and then you stop trying his hard. But like what's the difference? You know, we're like, oh the athletes career so short They should work as hard as they can for that period man life is short life is short for all of us You think you know your professional career of 40 years is like much longer than the professional basketball players 15 years It's not that much longer due to our life is short our time on earth is short So you choose how you want to spend the time on earth and if what you care about the most is like having a great life The work is not what gives you fulfillment and not the thing that you care the most about I think tech is awesome because we allow you to do that and still degree work and be creative and work with awesome people But I think if you really really want to have like the outsize impact I do think the incremental our works the incremental focus the caring more the thinking about it in the shower at night before you go to sleep Writing the extra email talking to an extra founder caring about the market a little bit more it all matters I do want to go a lay a deep beneath people though, and I want to discuss something that you said which I thought was fast and he said product differentiation is not a sustainable differentiation.

27:44Rav from a product person in the CTO, so help me understand this one. Great products have won for the last 15 years. We see that in consumer for sure, but we see that in B2Bs ass. Companies of the 90s and 2000s like PeopleSoft and Oracle, the UX is not good. But it solves business problems. Cooper or Bill .com. Suck. Yes, good point. Workday also sucks, right? But Workday is much better than PeopleSoft. It's just night and day and actually bill .com versus like a non internet billing system is incredible It is like earth shattering. Here's a couple of thought experiments. Imagine pre -stripe to stride you want to process credit cards It's like a hundred thousand dollar down payment.

28:24It's gonna take you six months to do through the contractual You're gonna get this shitty form compared that to stripe stripe. It's like you sign up on the website You can use the epi immediately once you have this amount of traffic they do a little more KYB on you, blah, blah, blah, you scale. The delta in that in value is like going from one value to 90 units of value out of 100. If you go to the Stripe website now and you look at what they've launched on the developer experience, it's awesome, but it's the difference between like 90 and 93. I think over the last decade on a lot of product experience, there's been a lot of competition on UX.

28:58But I think, given the current technology trends, a lot of competition has happened in UX and I'm not seeing UX ideas that are 10x to where we are today. Number one, and number two, you can copy UX. And this is really important. And there's a couple companies that are doing this right now. I think the most famous would be Ripling. We're like Ripling's building like the next workday. They've taken like, oh, this company does Adria Analytics. We'll like copy 90 % of their good features and we'll make an integrated version that works with your employee directory. You want to do like global billing?

29:27Like, we'll do a 90 % as good version of global billing. but we'll make it even easier because we'll deal with all the intercountry thing on our own. They do that and they're building a suite that basically takes all the vertical products that have one for verticals, integrate them into a combined experience and they don't have to innovate on pure UX for any vertical, then just copy the best. They're sounding sweet, right? And that's where the value will come from. I think the value won't come from out of this world UX. I think it will come from a suite of things that is cheaper, works better together, than the highly verticalized products that we've done today.

30:01Can I make a case, an alternative case, which is UX isn't innovated on now as it was before because of the maturation of platform life cycles, like we are at far into the PC, far into the mobile. My question is, do enabling technologies like Apple Vision and AI allow us new dimensions of UX that will recreate product differentiation as a sustainable? I think for the existing startups, what you've got to look at is it probably isn't going to be UX and there's probably going to be consolidation because we've oververticalized things by going after every like Bit of the software with a slightly bit better UX here there and I think the value now is going to be from tying it all together And there's a few companies that are doing that and I think those are going to be the big winners What do you mean tying it all together?

30:52Like there's the compound startup like Rip playing that. Yeah What do you mean by tying it all together being where the value is? That's a perfect example. I think you have to ask yourself like who lives in in Salesforce versus lives in like GONG in a handful of other tools. I think security tooling is the same way. A long or short Salesforce. Sales force to me feels like it's increasingly a database, a store, and not where the UX happens. But because everyone still has to store the data in Salesforce, it's still like the base thing that everyone buys. But like people are going after them. There's going to figure them out.

31:27I would say I am bearish on Salesforce ability to stay number one over the next decade. What it takes to win, if it's not around products, it doesn't focus on setting the right north star or understanding where to focus. How do you think about how to set the right core metric and what effective north star identification is? I think now compared to five years ago I'm more wary of like the one metric to rule them all. I've seen what I was saying, the difficult part of product not be solved by setting the right metric. It certainly helps, but it doesn't answer all the questions. So we have a metric around conversion.

32:02And it's the metric that matters the most or customers, meaning when someone tries to connect their bank account, are they able to connect the right bank account for that use case? And we do a ton to track conversion. But if you think about the work that we do on conversion, let's say you're trying to go from Paris to Milan. One way to go from one to the other is to walk. So you say your metric is like amount traveled like percentage of distance between Paris and Milan traveled So you go walking so that one's awesome because every day it goes down and you can predict very clearly when the person will get to Milan And then there's another person that the size take a train So what that person looks like is walking kind of in the right direction because the way train stations work in Europe They're journaling the right direction where the destination is they go slowly and then they stop there and then they go really fast And then you have another person that's taking the airport.

32:49So they're like going in the wrong direction, then they stop for a whole while, and you don't understand what's going on. And suddenly, they zoom over to Milan. That clearly the best mode of transportation, the fastest mode of transfer shift consistently is the airplane. And we know the airplane is better because we've done the work, and I know they exist, and they go. But a lot of product work, actually, at most companies on a metric, will incentivize the walking kind of behavior. Because it's measurable, it's clear that it's going to get you in the right direction in every day you see progress.

33:17The best work is the work where you're building an airport and inventing airplanes, and then a few years later, you can hop over from one place to another, not in 27 hours, but in one hour. So whatever metric you set, and you should have a metric and counter metrics to make sure people don't abuse it and don't gain the system and should draw that correctly, I think the really hard decision always is like, hey, do you do incremental work that has more guaranteed payoff? And how much are we willing to invest in things that could be real multipliers to the a product goal, but like you're not going to know for a bit if it's successful.

33:46And sometimes you won't know for a while and it's going to feel like it's failing. And what happens is your PM is at the airport and he's been waiting for his flight that's delayed. And suddenly he gets his text message from the boss and the boss says, okay, just take the train and that's stupid because he goes and take the train and then the airport, the airplane's ready to go and you miss the airplane. And that's what happens, right? You like start the project, it's ambitious. You work on it for nine months. The metrics aren't moving. You have revenue pressure and you're like, ah, we're not going to do it.

34:11I think the metrics are amazing. You need some way to judge whether you're making progress. You need leading indicators. You need North Star, then you need leading indicators of North Star, but you need judgment and gut. You can't abdicate the judgment and the gut to a metric. You need someone to go on limb and say, I believe that this will work. I'll put my promotion and my career on the boat. Like we're gonna have five people work on this thing. I think that's the part of product that's really hard. Do you do increment what today at Plankton? Yes, for sure. Yeah, and this year we have a conversion goal and we hit our annual goal on conversion in six months And we did it mostly through incremental work because people were smarter about looking for opportunities And it's a huge win for the business But we still have a home run on that and the home run matters more over any time that's conversion That's very difficult for competitors to get if you achieved it in six months Would you not say that as an effective goal setting?

35:04I had so far off you capped or could be done significantly If I knew the future, I would bet everything on the moon shots. I really fundamentally think that's the hard part of the job. The thing for me that's always clarifying, and I'm not nearly as good a product leader on this as I wish I were. We're building businesses. Long term, what matters is competitive advantage. It's a thing that you can do that is hard for someone to copy or expensive or someone to copy or who led last a certain amount of time. When you're completely like plied, where you already are better across the board than most of your competitors, I think the one rule for us is, what can we do to extend the window of our competitive advantage, even if we're giving up short -term opportunities to short -term increase the competitive advantage.

35:47It's hard to say no to the obvious short -term wins, and I wish I were able to do it more and to convince more people that we needed to look more at the things that over two to three years really win, because we have that luxury. We're ahead enough that we can invest in the two to three year thing. I'm one of your angel investments. How should I think about competition? I don't think I'm a very good angel investor because I like the founders and the ideas more than I do it for, you know, like financial optimization of the game in the early phases that I think if you're too focused on competition initially, you usually just don't build the right thing or you don't figure out the wedge that gets you to win and go to market.

36:22At any scale, like at Plaid scale, when you get to 50, 100 million in ARR, you're living in a world of competition. If you're making a lot of money at high margins, like people will come after you, then I think it starts to become important to have things that are difficult for others to do. So, you know, we were talking about product and product differentiation. The saying is always like distribution is your product. Your ability to get new customers and to sell more to existing customers. I think often a certain scale is what ends up allowing a lot of companies to grow more and more and more.

36:52Like, that's a high confidence way to grow. Reputation, network effects. If you can have brand, or much better network effects, those are incredible, but those are rare. There are a lot of successful companies that don't have huge network effects. So, you know, there's a hierarchy to competitive advantage and ideally you start to develop it But like at an angel with someone who has like a million in ARR, I don't know if you disagree tell me I just haven't focused on it because then I think very few companies would pass the filter like I would make like three Investments a year and not 20 I totally agree I'm just intrigued by something you said before those me which is your startup is a zombie and life is too short to keep trying You know, we always hear never give up and I'm always an advocate for never give up As your VC, well, I mean, I, VCs say, I mean, a lot of VCs are saying, give me the money back.

37:37I'll take 60 cents on a dollar. I don't think the most of the VCs care. I love good friends. I have a lot of like two friends, you know, like hang out in the weekends, adventure firms. I love them. They're great. I make fun of them a little bit, but... They make fun of them for what? What do we, because they're the fun, they're the fun. I don't think they work as hard as I do, but they make more money. I 100 % you just chose the wrong business. Yeah, I know. I just wouldn't be. They wouldn't make me happy. The way I think about venture capitalists and the value overall is they're distributing the chance at an outsize return.

38:05You find a lot of smart founders, you give them money and then some of them really hit it out of the park and you keep supporting them as they grow and make giant businesses. So if you think you're on a human level, it's like, well, a bunch of founders are going to fail. If you're measure for success as a $10 billion company, like 95, 98 % I don't know, some really high percentage of founders are going to fail. And that's just life. And so if you're a founder, you know that you're just part of a capitalistic machine to get to innovation and you do it Because you love it and because you believe in the mission for all these irrational reasons you do it But you always have to ask yourself like is this worth my time on earth?

38:41And as we said earlier life is belief is short and right now what's happened is there's a bunch of founders who raised a lot of money With businesses that in reality don't quite have the product market fit that they thought that they would and when that happens You got to be really, really careful because it's easy when you have three years of runway to spend another three years of your life Trying to make a thing that has a very low chance of getting to product market fit to work And I think a lot of founders are actually asking some of the question like reset Just do a totally different idea or like return your money and then decide if you want to be a founder again Or like start a product of the bigger company or whatnot and there's a lot of these I think there's zombies where they have some revenue, but they just don't have venture growth So you could turn into lifestyle business, but like, is I really why you want to start a company?

39:24It's not. Otherwise, you wouldn't have taken venture capital funding. And I think people are going to take good years of their life and of creativity. And they've been fooled into thinking they're close to Proc Marketfit because of the zero interest rate environment and the zero interest rate environment is gone. And they actually much further than they thought. The key for me is Proc Marketfit isn't a binary thing. Like, you don't have product market fit or not have product market fit. You have degrees of product market fit, right? And how easily people buy your things and that shows up in stats like CactLTV or whatnot, it's not like you have it or you don't.

39:55So I'll give you like a weird big company example, but it's really interesting. You think of snowflake, data warehouse. So I'm the CTO of a company. What's happening if you look at the snowflake numbers, it appears that their current customers rate of usage of snowflake, like the growth of what an existing customer would spend on snowflake isn't going up nearly as much as before. So last year before like if you were like average customer of snowflake that gave him a hundred dollars in year one They made give them maybe a hundred and thirty dollars in year two just existing usage no new sales just including usage But now that seems to be going up less at least that's what the like numbers look like what's happening What's happening what like gong is another example where I think for gong We like them because they make the team more efficient But we're also aren't hiring more salespeople and their model is seed based And so they're not gonna see as much intrinsic growth from all these companies not hiring as many salespeople Let's go back to the snowflakes.

40:44What's happening? Okay, here's what's happening before when my team was like, we want to put more data in snowflake. I was like, hmm, zero interest rate. So funding is free. Like literally putting more data in snowflake. I paid them, but there's zero interest rate on what I put in there. So it's easy to raise funds again. So I'm like, well, if in the future, I can generate return on this data that is above zero percent. It is worth it for me to pay for the cost of the data going in the data warehouse. Now suddenly I wake up and I'm like, well, the hurdle rate is 8 percent and I'm trying to get to cash with positive as quickly as possible.

41:15And I'm like, yo people, like, first, no more data into snowflake until you're really sure that you can generate much more value relative to the cost in the next, you know, 12 to 18 months. And number two, what are we storing in snowflake where we have really low odds of making more value out of it? You know, we're like, okay, we're going to reduce how much data we store there. Because the hurdle rate and the amount of value I think I can get from data products is just higher. Like the hurdle rate is higher. The value I need to show is higher. And so the product market fit for snowflake as a data warehouse product, that's the same binary.

41:45But the value of a data warehouse in industry just went down because the value that I need to generate from that data needs to be higher for me to be willing to spend that cost. And so everywhere right now in tech, what's happening is products that were top three value creation for businesses are now fifth on the list or seventh on the list. These companies that thought they had product market fit, there's a structural thing that's changed that's made their product market fit less. And in many cases less so that it's not a growth business anymore. And I think people are not thinking through it, they're thinking like, oh, it's a little harder to sell until there's more money in the market or until these companies start growing.

42:20And I'm like, no, actually, like, I'll still spend less on my data warehouse when I'm a cash flow positive because I need to get more value out of that data for it to be worth it for me to store it. I think it's a more fundamental change in how people look at returns. Would you be a long -ware short on stuff like? I don't know what their stock price is right now. I think Steve Billion. 60 billion? I'm short. Look, I'm a long term SNP 500 investor. Steve, you've kind of differentiated opinions. You said another differentiated one to me before, which is I don't have a mental model for generative AI, and that is a problem, but neither do you.

42:54But you wouldn't even buy it. I mean, what is a great product or engineering leader, or great business leader, right? You need clarity on what is possible and what is not possible. Like, what can you build with software? What can you not build with software? So what's really interesting about Genie I, it makes really cool demos, but I actually have a lot of trouble answering the question like where can we build great products with it, and where can't we? And I used to have a very good model of what you could do with software and to a certain extent hardware. You know, I understand what computers are good at doing with their bad at doing.

43:22Now suddenly with Genie I, there's a bunch of stuff they used to not be able to do, like deal with ambiguous human language or create new images based on words, that they're really good at doing. I just don't know quite what really good is like I don't have a sense for what they can or can't do there Look, that's my problem right and I need to develop that intuition because if I don't develop it I'll be out of a job like pretty quickly and I think that's true of a lot of people in tech like you really need to understand The bounds of technologies so that you can know what business problems you can answer with with software But I think everyone's in this situation.

43:53It's a work. We're in the early stages of it And it's so it's okay not to know was been the biggest career that you've made that didn't work out like product wise and a thing. But when I was a Dropbox, I was responsible internally for trying to build a Slack -like product. Basically, a product that would allow communication on top of the documents that are in Dropbox. We really, really didn't figure that out. That was big flop. I think we were too far from the customers. There's a ton of stuff in terms of early product that I got way wrong on that one. I learned a ton from it. JD, I love this.

44:24I could told you all day, which is wonderful for me, but I'm a VC, so we both figured that I have more time. I would have been media entrepreneur. You're a media entrepreneur, I thought. But I wouldn't finish for the quickfire on my friends. So I say, I shall stay with you and give me your immediate thoughts. Does that sound okay? It sounds okay. So tell me, you're a prolific angel as well. What's been your biggest lesson from real angel investments? It's really hard to predict at angel stage who's going to be successful. And I've been like renewed belief in humanity. When I see founders, then I'm like, ah, the idea is good, but I'm not sure this founder can do it.

44:57And then you see the founder change into like a unicorn of a human. I think an ability to predict people's ability to grow has been like a real, you know, eye opener If you could put all of your money in one company that you're investing, what would it be? I think it's these two. It's Rupa Health and Atlas. I love the mission the founders are awesome They like power through anything and I don't do it for the money I do it for like I think they have successful outcomes But I do it for how interesting the founder and the product is and I think those two are doing very cool things What's the biggest piece of startup advice to you here?

45:27There's title BS and why? The thing you should realize about all advice and the most important thing is does the fact pattern of the advice Match up with the fact pattern of your situation and often it doesn't and so what you take from the advice is like the delta between the advice and where you're at Which seed fund June Vastin if you could already invest first round I like those guys and I think they really care about helping founders get to product market fit They will sit and spend more time with the founders to help them get there than other funds that I know So that's why I have a ton of respect for them.

45:57If you can invest in a series A firm, which would it be? Wait, was he one of us upon a time you could just say benchmarked to that? But if hard for me to say not, it's not Sequoia. You know, even like, you know, Brazil and stuff, it's like, Oh, new bank, of course new bank is with Sequoia. Like, while we were all doing other stuff, you know, they're out securing that stuff. So, yeah, their records has been really strong. What do you know now that you wish you'd known when you started? This is piece of advice, which I think is good advice, that I give to people at larger companies, Which is like the best thing to work on is the thing that has impact for the business But that leadership doesn't care about you can unpack that piece of advice for a while if you're leader You can unpack that piece of advice and ask yourself sometimes what the best things for your business are happening Where you're not looking and what does that say about you as a leader and I think for employees It tells them like the North Star is having impact and having impact that any business is really hard because there's all these forces I get in the way like politics and internal incentives and whatnot But ultimately the impact is what matters.

46:52You got to find a way to work on something that allows you to have it. Final one, what would you most likely be remembered for as a leader? I hope that people who've worked for me around my teams or with me feel they did the best work of their life up to that point while they were working with me. If I could achieve that, that would make me very proud. JD, I've loved doing this. As you saw, you prepped for the schedule. I didn't state to it so well. But this has been a joy. So thank you so much, my friend. Yeah, thank you so much, it was great to chat and look forward to hearing the episode. I mean, that was awesome.

47:22What a broad and wide -ranging discussion that was. I want to say thank you to JD for being so open and so willing to move on schedule there. If you'd like to see more from us, of course you can on YouTube by searching for 20VC. But before we leave you today, when I talk about using Coda, it's not lip service or because it's in the ad copy. It's because I'm a believer. However, recently, Coda is the dock that brings it all together by putting data in one centralized location, regardless of format, so it eliminates road blocks that can stop your team in their tracks. With Coda, your team can operate on the same information and collaborate in one place.

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From the publisher

Jean-Denis Greze is Chief Technology Officer at Plaid where oversees global product business units across North America and Europe. Prior to joining Plaid, Jean-Denis was Director of Engineering at Dropbox. Jean-Denis is also a prolific angel investor with a portfolio including the likes of Nex Health, Merge.dev and Rupa Health to name a few.

In Today's Episode with Jean-Denis Greze We Discuss:

1. The Journey to One of the Most Powerful CTOs:

  • How JD made his way into the world of tech with his first role at Dropbox?
  • How does JD analyse a Linkedin CV today? What are the signals of outperformers?
  • What does JD know now that he wishes he had known when he started in tech?

2. Hiring the Best: 101:

  • What are JD's single biggest lessons on hiring the best talent?
  • What have been some of JD's biggest hiring mistakes?
  • Why does JD believe founders need to be as good at firing as they are hiring?
  • Does JD believe people can scale with the scaling of a company? If they do not scale, do you layer them or do you let them go?
  • How does JD determine whether to bring in an external candidate vs promote someone from within?

3. Product Differentiation is not Sustainable:

  • Why does JD believe that product differentiation is not sustainable? Why is UX as a moat BS?
  • How does this lead JD to suggest Salesforce is a short in the public markets?
  • Why does JD believe that Snowflake is also a short?
  • What does Snowflake teach us about the different stages of product market fit?
  • What are the biggest mistakes founders make when analyzing product market fit?

4. Remote Work, Titles and Entitlement:

  • Why does JD believe most tech employees treat their employer in the same way French citizens treat the French government?
  • How does JD analyse the impact of remote work on both productivity and culture?
  • Why does JD believe titles are BS in the beginning but matter with scale?
  • Why does JD believe that you should not hire for the long term?

More from The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

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20VC: Why Hiring in Tech is Broken and Founders Need to be as Good at Firing as they are Hiring, Why Product Differentiation is Unsustainable & Why the Current Generation of Tech Employees are Entitled and What Needs to Change with Jean-Denis Greze @ PlaiThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 50 min
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