AI meets HR: redefining people ops with DreamTeam's Shirley Baumer

0:00Welcome back to The Serial Entrepreneur, I'm your host Anna Wood. On today's episode, I'm joined by Shirley Baumer, the co-founder and CPO of Dream Team. Dream Team is on a mission to bring new life to how HR teams work via AI native platform that automates admin and allows HR leaders to focus on what matters most. We discuss the role of AI in HR, the story of Dream Team's co-founders meeting whilst working at monday.com and how there's growth to be found in uncertainty. Let's dig in. Hi Shirley, welcome to the podcast today. How are you? I'm great. Thanks for having me. Great, thank you for coming on.

0:46So we begin every single podcast episode with the same icebreaker question, which is what's your favorite breakfast cereal and why? Great question. I'm a mother of two toddlers so actually if I manage to you know grab some of their cereal leftovers before you run at the door so whatever comes in mind yeah fair enough so would you be able to introduce yourself and tell me a bit about your background yes of course I'm Shirley Ballmer I'm the co-founder and CPL of Dream Team we're an AI native people management platform I'm a second time entrepreneur and before dream team i was a part of the founding team at monday.com the fun fact i joined as the first ever product manager and we were back then 30 people and you know in a dream and i stayed through the wild ride so from six million when i joined to one billion in ars scaling to 2000 employees all over the globe uh one of the top performing ipos in 2021 it was a crazy ride it It was like being on a rocket ship and have to build it, you know, midair.

1:57So in Monday.com, I got to build teams. I got to build cultures, products from stretch and kind of fell in love with this chaos and decided to do it all over again. But this time in AGR. Yes. Great. So we will move on to kind of discussing your background in Monday.com. But to begin with, what is Dream Team? or would you be able to tell us a bit more about the company? Sure. So Dream Team was founded by our non-Near and I. We both met on monday.com. And essentially, Dream Team's mission is to help HR leaders to focus on the impactful people work and not the admin work. I think that people are the most important asset in building companies.

2:43We see it in Monday. We see it in dozens of other companies. but still HR professional kind of often find themselves dealing with the manual stuff, chasing people, uploading data, uploading data, pulling reports and it hurts the business. Contributes to the disperception that HR is less strategic often and I think it's absurd. I think that people are what makes companies good or great like it's a make or break kind of a thing. so our platform is that that's the mission like it's an ai native tool we help to cut off the admin work almost to zero i would say and it's proactive move the needle type of areas that can really push the company forward yeah great so would you be able to tell us a bit more about your product offering yeah of course my favorite part as a product person so you know at its core So Dream Team is kind of an all-in-one HR platform, but it's built differently.

3:47And it's built kind of more of an operating system than a traditional HR tool because it's super flexible and super open. So instead of forcing companies and forcing HR leaders into these rigid workflows, it actually lets them to design their own setup that fits to them like a glove. everything you need, nothing you don't need, and you don't need to hire this army of consultants or stitching together dozens of point solutions. Yeah. So in essence, on top of that foundations, we also build autonomous agents, which are like your smart little AI colleagues. We're really excited about them. And they, like I said before, they take all the messy, repetitive stuff of HR.

4:32yeah so companies can dramatically reduce the tools they use the operational overhead yeah we're really excited about that great is there a particular size of business that your products target or are you looking kind of at the big spectrum of businesses we're currently focused on companies like from 50 to 500 employees where you know you kind of you you need the structure but you don't want to the corporate bureaucracy part. So that's kind of our sweet spot. We're really strong in tech and also like financial services, business services. That's kind of the ICP, I would say. Great. So kind of take us back to the beginning.

5:20What problem were you trying to solve when you launched Dream Team? And what would you say the inspiration for launching the business was? My favorite part of the job. Building Monday really was an incredible experience. And I think that what made it successful wasn't necessarily, I don't know, the tech or stuff like that, but it was the people and culture. And I really believe in it and it really stuck with me. And I do believe that companies, like I said before, they live and die on how they hire, and how they onboard and engage and compensate and even part ways with its people. And yet, like the system that support these processes and these people felt outdated.

6:06So not necessarily bad or something, but just not built for the speed and complexity that modern teams need. And we felt it all the time in Monday. And, you know, it was crazy because every year we kind of outgrew the people tools and we had to replace them. and they couldn't keep up and and it and it took it all and and when we started dream team we said we want to do something completely different so flexible open and that actually can do the work for you and you don't have to work for for the tool um so yeah that was kind of the inspiration yeah so is it kind of your goal to be that that product that isn't replaced every year to be that product that stays with the company from say now until 10 years down the line.

6:58Yeah and every challenge that you're facing even not in scaling but the world is changing all the time we see it I'll also probably talk about it a little bit but there's COVID, there is war like the world is crazy, there's AI like so so many things that companies need to evolve all the time So when the tools are rigid and building in that in only one way, it doesn't make it. So we want to be there no matter what. Yeah, amazing. So you lightly touched on it earlier that you and your co-founder met whilst working at Monday.com. How do you think this experience impacted your mission and the way you're currently running Dream Team?

7:42Major, significant. It went like, you know, Anon and I, we survived hyper growth together. So that creates a bond, hyper growth and steroids, scaled from 30 to 2 ,000 people. And as I said earlier, you know, during my times in Monday, we had COVID, we had the war in Ukraine, we had political chaos in Israel, we had October 7th, you name it. And somehow, like really miraculously, every hit Monday kept growing and kept becoming better and better. I think it was the most resilient group of people I ever worked with. And just being a part of that was truly inspiring. So at its core, our approach to people management at Dream Teams is very similar in essence to what Monday did for work management.

8:31Like Monday that entered, you know, super crowded, super commoditized, even market full of fine enough tools, but was still able to change the game. And the essence was flexibility and it was simplicity. So I don't know any product almost out there that can morph into CRM, to DevTool, to ticketing system, to project management tool. And that's unique and still be very delighted to use. When I was a product manager, a product executive in Monday and talked to people, they sometimes proposed to Monday, Like, can I marry you? Or, you know, they think about the sourboards in Halloween. It was insane, this level of customer, you know, love and obsession.

9:18And I think it's really, really rare, this combination between flexibility to the extreme, but also simplicity. And I think it gave us some serious unfair advantage, like learning from the good and learning from the bad. and we're kind of taking the same mindset into a jar, which is, you know, let's be honest, it's a very crowded market. There are over 5 ,000 point solutions. We don't want to be the 5 ,001. We want to rethink the category. So, yeah, and you know, even beyond the product, we carry the value that shapes us in Monday. So radical transparency and extreme ownership and speed. So that's our DNA, day one.

10:05Great. So what was that moment that you and your co-founder decided to come together to found Dream Team? It was 2023. We just left Monday. We felt we wanted to do the next big thing. And we found during our experience in Monday, this amazing opportunity we felt in the HR field. we wanted to to give it a try to do it ourselves great so i think you also mentioned it earlier so what do you think is the current role of ai and hr and where do you think the future of hr tech is heading in the next five years yeah in hr is one of my favorite topics you know i think it's like somehow uh like the early days of gps in cars you know it's there but people didn't trust it So they still had to print out the directions just in case.

11:04So it was there, but I think it's the same. I think that it's there sometimes, but people don't fully use it or don't fully like utilize it to the extreme. But I think it's changing. Like I think we're already seeing AI take some of the mundane operational tasks, like summarizing feedback or nudging managers. and that's a lot because these type of things you should get up like hours of HR times but in five years I think it will be a completely different game like I think that AI agent will just run their own processes, multi-step complex use cases, crossing platforms and do it by themselves so and that will lead HR to be not like an enforcer of compliance and policy but like to be kind of cultural architects so I think that role of HR will fundamentally change.

12:06So you also kind of likened the current state of AI and HR as the early days of GPS where people would print off a map still just in case. What do you think will get businesses to the point that they feel comfortable and more willing, I think, to embrace AI in HR? I think, first of all, I think like any other major innovation, it sometimes takes time. But things in AI change so rapidly that I think everyone should be on it and try to hop on the train. um i think that what would really be meaningful is that when ai will be fully baked into current hr workflows so it won't be addition it won't be look at this school technology what this school technology can do but actually when you want to do stuff when you want to build a performance review or when you want to change a policy you have a new office i don't know in the philippines and don't know what's their maternity leave policy.

13:13So yeah, I can tell you. And you want to promote someone and you don't, and it offers to do all the paperwork, the contracts, the scheduled meetings, everything around that. I think that's where the magic will happen. So kind of almost seamless integration into workflow. And I think we're not there entirely now. I believe that will be the turning point. and that's also our focus. Do you think kind of trust in AI as well as education in it will help that kind of uptake in AI products? For sure, but I always believe that when you experience things firsthand and when you have a problem and AI is there to help you and you really experience this aha moment that I remember how I did it before, but now it's really on the minute that I have a problem, it helps me.

14:16I feel it's much more powerful than another training session. It's always good. It's not bad. I think education and awareness and training is a very positive thing. But I believe that the major shift will happen when you really, really need it. And it's critical. and it significantly helps you. So when you have this experience over and over and over again, I think it's very powerful. Yeah, definitely. So you discussed about AI agents. So how do you think that AI agents in the workforce are impacting HR? I like to think about it like you have a team of very enthusiastic HR interns, you know, who are just obsessed with follow-ups and schedule meetings and never forgetting anything.

15:07This person has a birthday. This person didn't get a raise. This person's sick days or vacation days are going to get lost because they're not accrued from last year. They're always on top of everything and they kind of do the work for you and work in the background. And as I said before, I think it will allow HR actually to be more human and not less human because when the grant work will get off their plate and they can focus on the work that humans can do, actually listening, actually coaching, actually navigating complexity, building trust, these type of things AI will never do. But when humans are drowning in bureaucracy, they don't have the headspace, I think, to do.

15:53So, yeah, that's my take. I think AI would be leaner. I think it will be more strategic. I think they'll be even more critical. to the business. So less admin, less compliance, more impact, more business impact. That's, that's, I really believe in it. Yeah. So I also think it's, it's hard to have a huge impact when a lot of your time is spent up doing those little admin roles, which may be five minutes here, five minutes there. But then at the end of a month, that might be a couple of hours that you spent just doing those small things that AI could have done for you. And lots of like context switch also.

16:37That's what I witnessed, that HR work is very, like a little bit of this, a little bit of that, like, you know, turning fire here, turning fire there. And it is very hard. It is very hard. They're expected to do a lot, to be a, you know, technical wizard, to build workflows to analyze data to work with people to coach managers I think it's a lot I think the expectations are really really high and almost unlike and not realistic sometimes yeah definitely so kind of coming back to the experience I'd say is what challenges have you faced on the dream team journey so far and how have you managed to overcome them where should I begin.

17:23You know, on a more serious note, I think one of the most intense challenges, it wasn't even business related so much. It was kind of navigating the recent war with Iran while trying to keep a start going and support my team and care for my family with very young kids and kind of juggling all that while running to shelters five times a night and facing a real threat to your life. It was intense and it was overwhelming. Just to acknowledge the toll that it takes on civilians, on Palestinians, on Iranians, on Israelis. And it was very, very challenging. I find myself doing the Q3 roadmap and trying to put my baby to sleep.

18:12And just a few hours later, waking up to sirens, grabbing my toddler, running in the streets, looking for shelter it was it was surreal and then few hours later on an investor call and it was very very surreal and i think that what helped was letting go of perfection focusing on what matters like creating clarity to the team structure to the team compassion to the team you know we we let the team and we gave them full autonomy so you don't need to attend any meeting just clear priority, like clear focus. Every person had one mission that's tightly aligned with our goals and it's tightly, highly impactful, but no more juggling.

18:57So I trust people to execute like business critical role. And, you know, somehow in the middle of all of this chaos, we did make progress and we won. and I'm incredibly proud of my team for doing that. And it was also another reminder about leadership and like a different type of leadership, not having all the answers, not being strong all the time, but just show up, you know, be honest, be human, be vulnerable, even when the world is literally on fire. So that was a huge challenge. It's still a challenge. Working through it. I think that's quite interesting. I think what you just said is very parallel to what you were saying, that your experience at monday.com was that even though there was a lot of uncertainty, saying something like COVID, but Monday was still having a lot of growth in that.

20:03So I think it's kind of something to take away is that there's growth in uncertainty almost. Yeah. So I think on a bit of a light note, what would you say have been the highlights of the journey so far? For me, it's always like talking to customers, like the small stuff, you know, this new feature saves me hours. Something I used to struggle with, I don't anymore. I don't need to worry about it. So like these tiny highlights that basically happens every day. But for me, that's what keeps me going. Not the big stuff, the everyday stuff. Amazing. Yeah, it must be great knowing that something that you've built is getting positive feedback.

20:47Something that you've put so much time and effort into that your customers are saying, yes, this is exactly what I needed. And it actually matters. it actually matters to me day to day how I do my work and impact the company and even being perceived I think it's important as a founder to have that mission and really kind of have that importance on what you want to do and still really be dedicated to wanting to help people in HR or no matter what you do really having that mission of what you started with in mind because it really helps drive you to what you want to do so what would you say have been the lessons that you've learned on the journey so far we talked about it a lot for me it's like resilience and discipline win everything it's it's challenging like building a startup It's not a small sailing.

21:51It will never be. And there will always be challenges, like the market changes, global crises, and personal stuff sometimes. And I think in what I've seen firsthand and from companies I work with, that the best teams, they don't try to avoid challenges, but they know how to push through, and they know how to overcome, and they know how to adapt, and they know how to stay focused, and they know how to be compassionate. I believe that's what you know separates the good from great yeah definitely so kind of looking back at your time at monday.com what lessons did you learn there that you feel has helped you in building your current startup a lot I touched upon it a little bit but I think also just very product technical aspect of it during my time in in monday i touched on you know consumer focus product technical product platform product and this experience of building a platform like as i said that can be so flexible and so open not i don't know a lot of products on the market that are like that it's very very unique and and i learned from it like how to do it well and also from what we didn't do well and try to fix you know after five years it's very hard to to redo some things and we from the beginning uh from scratch and and also yeah how to lead how to lead the company I think that Ruin Iran and Hufvind and Likman they are exceptional.

23:42Exceptional leaders like honest, bold, very inspirational. Yeah great. So working the HR tech space that people make it up, what would you say the people that surround you and your team mean to you as well as the business? It's everything like I get Like, it's my energy waking up in the morning. Like, I walk in the office and I see the people who work here with all their energy and time in your team. And it means the world to me. And we're very much occupied by that, like how to create, how to bring the best people. We don't want to build a company which is huge. and we want to build a company which is lean and excellent and and how to keep this balance so from one hand to help people and to feel um good and you know well balanced and to keep their well-being but from the other hand to push forward like we want to build something extraordinary so you can do the regular stuff if you're doing extraordinary so keeping this balance all the time we're very much occupied by that and like you said it's very much aligned with the space where we are at so we always think about that like how can you know we build dream team how we can be the change we want to see in the world we are very occupied yeah I do think that's really important And how big is your team currently?

25:24Currently 30 people. So keeping it lean, the best people I've ever worked with. That is a very impressive feat to have 30 and then still be seeing the amount of growth that you're seeing. And so I think you lightly touched upon it about competitors. So how do your products compare to competitors and what makes them stand out in the industry? so two main things i also already touched upon that a little bit but one uh so like the flexibility and openness versus like rigidness however you like we believe the customer is no best we we don't uh hold the truth like sometimes some of our competitors it's it's also very beneficial but sometimes they say we know how hr processes should look like and like confirm and we don't believe in that maybe because we're not HR people ourselves okay but I see it every day every company works different I think we are here to help them out do their best and work the way they want we don't try to force them into doing that I think that's one aspect another Another aspect is everything around AI and AI agents, which is very unique.

26:46And we really, really believe in that. Like let AI agents actually do the work, not just remind you to do stuff, summarize something, like actually do the work for you. And third, I think that's a choice, but we are focused on SMBs and that's kind of a niche. It helps. We are hyper-focused on that. And so the feature set is perfect for their needs. The price, we're much more competitive than most of our competitors in terms of price. So it makes economical sense. You don't need to buy 10, like your HR tech stack don't need to be made of 10 different tools, which each one of them is super expensive, but you can have one tool that fits to you like a glove.

27:38So two product stuff and one more commercial or DTM stuff. Fantastic. So what's next for Dream Team? Do you have any features or markets or any missions that you're excited about and can talk about? Yeah, sure. We're doubling down on the HR agents. So building towards true HR autopilot. So as I said before, it's not just surfing, seeing insights. It's actually doing the work for you. like imagine you're a VPHR you wake up in the morning so the dream team agent already flagged there's a new paternity leave law in Greece and it already updates everything the profile and the policies and it can say hey there is Jane who is a top performer but we believe she's searching for other jobs and it can trigger a retention flow or promotion or raise or stuff like that, or, you know, you launched a new work from home policy, just some examples.

28:42Yeah. And, and, but people, there is a negative buzz around it and people talk about it. Should I draft clarification message or should I change something? So actually, actually doing the work. And that touches upon another thing, which is kind of agent to agent collaboration. So not only very specific to the task you are doing now, like building onboarding flow or building performance, but the agent actually talking to each other, like colleagues or workers can talk to each other. So onboarding agent that syncs with IT provisioning agents to make the workflow really, really end-to-end. So no ticketing, no micromanagement, no manual follow-ups.

29:22so taking this HR workflow and really taking them like end-to-end almost automated so the HR can see it review it adjust it but not actually do the work okay it's also worth to mention like it's not fully autopilot it's usually dealing with very sensitive stuff right like hiring and promotion and salary adjustments and stuff like that so it's not like doing the work in the dark but doing the work and the HR can see it can approve it can adjust it can tweak it but focus like I said in the beginning on the important stuff on the human part of the job yeah just having an assistant to kind of flag all those things that may take a while so you can look at it and say yeah that that sounds good to me yeah that sounds good that's uh great but let me do these little tweaks that no so kind of taking this role instead of like uh doing the the work themselves yeah great so you also said you're currently um focused more on kind of the smb market in the future would you be looking at um rolling out to bigger businesses or do you think you'll be doubling down on your target market it's hard to say but currently we believe we will go for larger companies as well and i think it's a journey like as long as our also product you know will evolve will mature will be deeper it can be a greater and greater fit for larger companies as well.

31:11Again, Monday.com, I keep bringing it up, but when I joined Monday, the average team size was five. Five people. Super, super, super tiny teams. As we evolved, and actually I led this effort of going to enterprise, now Monday.com, most of their clients are enterprise clients, and most of their revenues our enterprise from it comes from enterprise clients so full transformation like not ditching the small ones so keeping both of them that's also very meaningful i think and that's also for us meaningful because often what companies do they they choose size the sites sorry like either the small ones or enterprise one it's very hard to combine these two motions it's very hard to combine self-serve, no-touch, small accounts, product-led, and enterprise sales, hardcore, which is more sales.

32:14It's very, very difficult, but I believe that done right, like we learned from Monday, again, from the good stuff and the bad stuff, it can be magical because the small ones, like the gain, is that the small accounts get a robust and powerful platform, and the big ones, they get very easy to use, friendly, intuitive platform and often it doesn't work together. So we want to crack that. Okay, it's difficult, but we're aiming to go there. But again, like, I don't know, the world is changing twice a week, so it's hard to commit. But that's definitely the direction. Yeah, especially as I think it means you can kind of grow with some of your clients.

32:55Some of your clients are also startups from really just starting who eventually might end up being huge enterprises. It means that you could move along with those clients. Definitely. We started with that, right? I told you, I shared with you in the beginning that what I saw is that tools weren't able to keep up. And so that's our promise to our customers. Like, you will never hit a wall. We will grow with you. that. Amazing. So that comes to the end of my questions. But my final question is always, do you have anything else that you wanted to add or plug for the end of the podcast? Just, I really believe after talking, I'm not an HR person.

33:44But the last couple of months, I spoke to dozens and dozens of them. And I believe that HR deserves a seat at the strategic table and I think the best performing companies in the next decade won't be the ones that will have the best AI and the best technology they'll be the ones that will build healthy organizations high performing, humor centric teams and organizations using AI and that's a big difference and that's what we aim to do Amazing, well thank you so much for coming on the podcast today Shirley It has been amazing talking to you and learning more about Dream Team. Thanks for having me.

34:28If you liked this episode, be sure to subscribe to the podcast and check out Startup Magazine's socials to stay up to date on the latest Startups news.