The following interview is a conversation we had with Jennifer Dulski, CEO & Founder of Rising Team, on our podcast Category Visionaries. You can view the full episode here: $11 Million Raised to Build the Future of Team Performance

Brett
Welcome to Category Visionaries, the show dedicated to exploring exciting visions for the future from the founders who are on the front lines building it. In each episode, we’ll speak with a visionary Founder who’s building a new category or reimagining an existing one. We’ll learn about the problem they solve, how their technology works, and unpack their vision for the future. I’m your host, Brett Stapper, CEO of Front Lines Media. Now let’s dive right into today’s episode. Hey, everyone, and welcome back to Category Visionaries. Today we’re speaking with Jennifer Dulski, CEO and Founder of Rising Team, a team performance platform that’s raised 11 million in funding. Jennifer, how are you doing? 

Jennifer Dulski
Great, thank you. 

Brett
So I see you started at Yahoo in 1998. So for a lot of us, that’s a crazy idea to think about. Yahoo at its peak, the massive, successful company. It was. Talk to us about what it was like to be at Yahoo at that time. 

Jennifer Dulski
It was incredible. Honestly, it was so cool to work at Yahoo back in those days that when you first started, they gave you a little license plate holder that said, do you yahoo? And I didn’t even put it on my car because I thought it was too like show off y to show to everybody that I worked there. And it was just, you know, sort of like those early, exciting days of the Internet. This obviously makes me just sound old now, but it was incredibly fast growth, high paced growth with a really strong and talented and passionate group of people. And many of the people I met and worked with in those early days have gone on to do other incredible things. 

Jennifer Dulski
And that’s one thing I always remind people to think about in their careers, is like, all these friends you make along the way, we all become other things. And it’s a great network and set of friends to have. 

Brett
Now, I’m going to skip around a little bit, but I see you are also the head of groups and community at Facebook. What’s the biggest difference between Facebook and Yahoo when it comes to culture? 

Jennifer Dulski
Yeah, you know, again, I was at Yahoo when I started. There was 400 people. And by the time I left, the team that I ran was bigger than the entire company was when I started. So I saw that super fast period of growth. By the time I got to Facebook, it was well over, you know, tens of thousands of people. So they were different in culture just because different stages of company. The thing that they had in common, though, was really talented, passionate people who were very self motivated. Like in some of the companies I’ve worked at, we’ve had to spend a lot of time talking about sense of urgency and velocity and never, ever had to do that at either Facebook or Yahoo. 

Brett
Interesting. Now, let’s jump into what you’re building today at Rising Team. So can you just paint a picture for us at a very high level? What does the platform do? 

Jennifer Dulski
So we build software that helps leaders build high performing teams, and we do that by helping them in two ways. One is we give them software to run fun, deeply connecting interactive workshops with their teams without needing an outside facilitator. So usually you have to hire someone. It’s very expensive. We help you diy those sessions. And then the second piece is that all of the insights you learn about your team from those sessions that you do synchronously. Go into a hyper personalized AI coach that then knows everything about your team, and you can ask it for advice, and it will give you personalized advice about each team member. 

Brett
Take us back to April 2020 and the founding of the company. I have to comment on the fact that’s probably an interesting time to start a company because that was, what, two months into Covid? 

Jennifer Dulski
It was so interesting. So I actually hatched this idea in, like, February of 2020, and I started, you know, bootstrapping it. I wrote the outline. I started thinking about how to prototype it, and then I actually incorporated the company in April. So when I first hatched the idea, the pandemic hadn’t even started. You know, I built this because it was the tool I wish I had as a leader of teams throughout my career. I always wanted something like this, and it never existed. And then the thing that I thought was important overnight became urgent to everybody because building more connected, engaged teams, you know, when everyone’s team was remote, all of a sudden everyone really needed a way to help them do that. So I think it was serendipitous, Trey. 

Brett
And then from that original idea that you had there in early 2020 to the idea today of the platform, was there an evolution at all, or was that idea that you had really similar to what you ended up building? 

Jennifer Dulski
There definitely was an evolution. And in fact, for very first version of the product was built mainly for managers to use one one with each person their team. And it had the same kind of set of assessments and tools that you could use, but it was meant to be done individually. And then what we realized and what was the huge unlock for the growth of the company was that doing this as team would be more effective for two reasons. One is it saves a lot of time, you know, it’s much faster to get the whole team together in one meeting than to meet each person separately and the other is teams really crave this. They really want to know each other better. They want to feel more connected. And especially in hybrid and distributed work, they feel that strongly. 

Jennifer Dulski
So it had an extra benefit. 

Brett
What about your market category? What’s the category that people are buying? Is it a team performance category? Is that the category or how are you thinking about that? 

Jennifer Dulski
Yeah, it’s pretty interesting. We call it a team performance platform. I believe that is in some ways a new category. The categories that we tend to compete against are either learning and development. So learning management systems facilitators, they hire to do trainings or team engagement, measurement and movement, and then possibly a third category, which is kind of just pure team building. We’re kind of a hybrid of those things because we build software that helps you run these team building sessions, you learn skills along the way. And we have a bunch of data about how we move employee engagement. So it’s a little bit hybrid between categories, which can have its pros and cons. 

Brett
And then are you trying to capture the demand that exists for those categories to say, no, no. What you’re actually looking for here is a team performance platform. 

Jennifer Dulski
Essentially, yes. I mean, we often come in through one of the, if you will, jobs to be done of things like my pulse scores came back and they’re really bad. I need help moving them or I no longer have an off site budget. How do I still keep my team connected? So there are certain pain points that we enter in and then we explain that our offering is actually better than the other alternatives out there. So again, its going to be way less expensive than an off site Orlando, you know, coaches and facilitators and oftentimes more effective in moving the numbers people want to move. Our goal, though, is to complement those things. Like, we’re not trying to say, you know, you never want to hire a coach or facilitator. 

Jennifer Dulski
It’s just that oftentimes you can only afford that for so many people in your organization. And if you want to give something to everybody in the, you need something more scalable to do that. 

Brett
Trey, in long term, is that the category that you think it’s always going to be? You know, is it always going to be team performance? Are you going to try to build this into a category and there’ll be competitors in this category, or is this more just a kind of short term way to be different in the market? And eventually you will absorb a different category name or a more mature category that already exists. 

Jennifer Dulski
Yeah, it’s a great question. I think there’s a number of ways we could go at this point. And what we see already is that companies are finding a strong need and strong value in what we provide. So regardless of what you call it, and they may think of it as a learning thing or a team building thing or engagement, they are finding value. We’re seeing things like big customers who sign multi year renewals and things like that. Over time, especially as the AI portion of what we do continues to evolve, I could see us getting more into one or more of the other existing categories. So, for instance, right now, our AI itself is a coach, and it also, over time, will do things like help you write your performance reviews or do your one ones. 

Jennifer Dulski
And there are certainly other companies in all of those categories. 

Brett
From a marketing perspective, what’s the high level marketing strategy look like? 

Jennifer Dulski
So our marketing, we tend to sell to functional and divisional leaders at large companies who have these pain points, right? So sometimes it’ll be a CMO or a CIO or a VP of engineering who says, I really want something like this for my, you know, they’re feeling disconnected. They work all over the world. I don’t have money for off sites, or I can only do one off site. Or again, my pulse scores are bad. And those people have a real need, a real pain point, and have some budget. And then typically we enter a company in that way, and then the data shows how well it works. And then other people inside the company want to get involved and use it for their organization. So, you know, as an example, we have a big tech company, we have their cloud. 

Jennifer Dulski
And then just yesterday, someone from their cloud moved to a different part of the organ, says, now I want to use this over here. So that’s kind of the main audience we sell to. And then in terms of the go to market motion, we tend to find people through when they are looking for solving those points of pain. So, for instance, we have a psychological safety blueprint that we offer. And a lot of people are searching for how to improve psychological safety in their organization. So thats usually how we find people looking for their needs. 

Brett
Trey, what about all these big, amazing logos that you have? What was that first big logo that you’re able to land or maybe the first one that you were able to land that you can talk about, you know, how did you pull that off? How’d you land that logo? 

Jennifer Dulski
It’s a good question. I mean, we have a lot of big logos at this point, right? We have Google and Cisco and Airbnb, Yahoo and others. The first company we actually signed was the bank of Hawaii, which is pretty interesting. We got an introduction to them and, you know, sometimes it just takes a like a passionate early adopter and you wouldn’t think necessarily of a bank as being an early adopter, but in this case they had a CEO who said, yeah, I really see the potential here. And it’s kind of like the, you know, crossing the chasm book. You just need some of those early people to take a bet on you. And they did. We started with a pilot. The pilot went extremely well. 

Jennifer Dulski
Then they rolled out to, you know, more of their organization and within, I think under six months, they decided to push it out to the whole company. And now that we’ve been working with them a few years, you know, the data is just so strong. Like you can see based on the number of Rising Team sessions people run, their engagement scores go higher, their manager effectiveness scores go higher. We just got data back that shows we drive a significant lift in employee retention for them. So the early adopters of the product have probably seen the most benefit, too. 

Brett
What about the marketing team? What have you learned so far in building up that team? And how big is the marketing team today? 

Jennifer Dulski
I have a marketing team of one right now, but our go to market team as a whole is probably 12345 people, maybe six. Five or six people if you count marketing and design and a data person and some sales and customer success people. We’ve got five or six people on that side. And at a startup, our number one value at Rising Team is we’re all one team. And so the idea is when things need to be done, people are going to raise their hand and they’re going to jump in and do it. And that means everybody does both their job and things that may be slightly outside the scope of their job. And that’s how we learn. We run a pretty rigorous growth experimentation process, so we have hypotheses and we test things. 

Jennifer Dulski
We try to test as quickly as possible to see what’s working. And, yeah, we have a lot of what I call pea shoots, promising pea shoots of channels that we’re just getting ready to be able to invest more in. 

Brett
Can you share an example of an experiment you ran that you thought it was going to be a success and it turned out to be a flop, or turned out not to be as successful as you thought it was going to be? 

Jennifer Dulski
Yeah, I mean, I think that there are experiments that go both ways. Right? So, like, we recently, one that we did that surprised me on the good side was we redid the landing page for where people sign up for demos. And one of the things we had been struggling with is like how to route people to the right person based on their company size or their size. And we previously had just been sending them all into one bucket, and so we updated the form to add sort of more fields so that we could better sort them. And it actually ended up having a much higher conversion rate, too, which was really surprising to me. So sometimes I get the opposite surprise. An example of one I thought would work better than it did is the chatbot on the homepage. 

Jennifer Dulski
So I thought, everybody’s got to have a chatbot. And so we put up one and we started with manual answers to it, and it hasn’t been yet that meaningful for us. Maybe we need some more iteration on it. 

Brett
As you reflect on the growth that you’re seeing, and just from a go to market perspective, what do you think’s been the most important go to market decision that you’ve made so far? 

Jennifer Dulski
So for us, the most important decision has been how we think about pilots. So when I first started, I was like, we just need to get people to use this, whatever it takes. And I offered unlimited teams for $1,500 for some short period of time, and a lot of people bought it, but then they didn’t really use it. There wasn’t really an incentive to get going with unlimited teams and so forth. Over time, we’ve adjusted the pilot experience, and the biggest learning we’ve had is that initial pilots need to have enough people in them and be run over a long enough time period that we can gather data to really clearly prove ROI. So we used to, as I said, do a short time period, unlimited teams. 

Jennifer Dulski
Now, we usually say people should run a twelve month pilot, and depending on the company size, it’s usually several hundred people, because that’s what gives you statistically significant data to prove that it’s working. And that’s what then gives people the reason to see the ROI and continue expanding. 

Brett
What about lessons from fundraising? So as I mentioned there 11 million raised to date. What have you learned about fundraising throughout this journey? 

Jennifer Dulski
Yeah, I think so. It’s funny we haven’t talked about it, but I also teach a classes at the business school at Stanford about how to scale growing companies. And so a lot of these topics are things we talk about in class and it can be one thing to kind of teach it in class and it’s another thing to live it. And what I have found is that the key is to find investors who are really aligned and long term focused. So its not necessarily true that the people who give you the absolute highest valuation and the absolute most money will be the best investors over the long term. 

Jennifer Dulski
And I’ve seen this really well because I teach in class where I bring in guests and we do cases of other peoples businesses and there are so many examples of people kind of choosing the wrong investors. So I feel like we’ve chosen our investors very thoughtfully and we have an incredible group of investors who feels really mission aligned, really focused on the long term, really supportive of the company.
Brett
I also want to ask about your book. So I did order a copy, so I have one coming. Talk to us about the decision to write the book, the goal of writing the book and then what you’ve learned from that journey. 

Jennifer Dulski
Yeah, so the question is, where is it going to go on your color coded bookshelf? Because the spine is turquoise and red and yellow. So it’s really, you’re going to need a rainbow section if people haven’t seen it. Brett has a really beautiful color coded bookshelf. So I wrote the book. So I started writing the book when I was president, comma, which I did for about five years, helping scale that organization around the world. And what I saw was really surprising to me in a way, which is that people who started these world changing campaigns and movements were doing very similar things to the entrepreneurs that I saw starting companies in Silicon Valley and what I had been used to as an entrepreneur myself. 

Jennifer Dulski
And so I thought if I could just help more people understand this set of steps and skills that you need to start a successful company or a successful movement, that more people could do it and we could create more positive change in the world. So that was the premise behind the book. 

Brett
How long did it take you to write it from start to finish? I guess we can maybe say you have the idea. How long did it take until it was out the door? 

Jennifer Dulski
Way longer than you would think. Funny, because having worked in tech my whole career, I just could not believe how slow it was to write a book. And part of the issue was I worked with a publisher. So the book is published by Penguin Portfolio. They were amazing to work with. It’s just an industry that works at a very different pace. So even after the book was completely written, it went through months and months of copywriting, edits, then going to the printer and so forth. So I think people who self publish books can get them out the door much faster. The actual writing time for me was probably maybe six months or so. 

Brett
And what were those objectives? Obviously, that’s a big chunk of time to invest. What were you trying to achieve with the book? And did it achieve it? 

Jennifer Dulski
Yeah. So I get a lot of questions from people who want to write a book, and I always ask them this question up front, what is your objective? Because if your objective is for a lot of people to see and read your content, it is way better to publish online than to write a book. Far more people will read what I write on LinkedIn, in fact, or I sometimes write fortune or whatever. More people will read a single post than I put online than will read the book ever. So that’s just something to keep in mind. That said, a book is a real legacy in a way that online writing isn’t. Not only did I write it, but I also recorded the audiobook. 

Jennifer Dulski
I thought of it as kind of a legacy, even for my children and for sort of the stamp I wanted to leave on the world. And for that, it definitely hit its objective. 

Brett
Trey and ill move in here to the final couple of questions that I have. So, im based in San Francisco. You’re in Palo Alto. I believe you’re teaching at Stanford. How important is it to be in Silicon Valley or in the Bay Area today? If you were starting your career again, imagine you’re in your early twenties, just starting your career. Where would you go? 

Jennifer Dulski
That is such a great question. Part of the reason I came here, a washing, obviously the center of tech, but also I grew up in San Francisco, so it was also home for me. And I had that reason to come back here, too. I do believe if I were starting a career in tech, not as an entrepreneur, but just wanting to work at one of these kind of big tech companies, which is what I did early in my career, that I would still come here. I mean, I think there are a few places that are really relevant for that, and I would try to go to one of those places. It might be sf, it might be New York, it might be Austin. 

Jennifer Dulski
But as a kind of young person wanting to go into an office and be in the center, I would probably still choose one of those cities if I were just starting out as an entrepreneur, though. The amazing thing is you can really go anywhere. Like, you just don’t have to be here, even if you want to raise money from funders who are out here. You know, I raised all the money for Rising Team on Zoom. There was only one investor I met in person before we raised money from them. And I’ve met most of my investors since, but I haven’t even met them all in person since then. So the world has completely changed in that way. And that, I think, opens up. 

Jennifer Dulski
And also, our company is fully remote, so I’ve hired people from all over, and that has been, you know, just a huge upside for how we get to hire people. 

Brett
Trey, final question for you. Let’s zoom out three to five years into the future. What’s the big picture vision look like? 

Jennifer Dulski
I have huge vision for Rising Team because I believe that we can help every team on earth be more successful, more connected, and more engaged. And we’re starting to see that happen already because we have Fortune 500 tech companies, but we also have school teachers and government agencies. I have, like the Massachusetts probation officers use Rising Team, and they all see the same kind of results. So when I think about the next three to five years, there’s a few big things on my list. One is expanding our AIH offering, as I mentioned. So we offer what I believe is the best of both worlds, deep human connection, plus AI to help you remember all the things you’ve learned when meeting people. And then the second big bucket is moving to hourly and frontline workers. 

Jennifer Dulski
So a lot of our customers today use it in corporate settings. But we launched what we call mini kits, which are ten to 15 minutes long and can be done on mobile devices. And so we’re starting to move into factories and retail stores and bank branches. And I think, I believe we can make an even greater impact on the workplace by reaching workers like that. And then the third piece is that we’re platformizing what we build at Rising Teams so that not only we can build content, but other people can build these scalable, interactive workshops on the platform. 

Brett
Amazing. I love the vision. I really love this conversation. It’s been a lot of fun. Before we wrap here, if there’s any founders that are listening in, they want to follow along with your journey. Maybe buy your book. Where should we send? Where should they go? 

Jennifer Dulski
I am almost everywhere, so please follow me on LinkedIn. I also have a newsletter you can subscribe to and then our company is at Rising Team HQ on X and LinkedIn and so forth. 

Brett
Amazing. Well, thank you so much. 

Jennifer Dulski
Of course, I should also say risingteam.com is the website, so please check out the website. 

Brett
We’ll link there, and we’ll also link to the book as well. But it said I had the last order, so we may need to restock the book. 

Jennifer Dulski
That’s just per seller, so when you buy, then some other seller will pop up. That’s Amazon for you, right? 

Brett
Oh, got it. It definitely made me want to click like purchase, so it’s worth it. Amazing. 

Jennifer Dulski
Likewise. Great to talk with you. 

Brett
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