Episode
52

She Sold Her First AI Company to Google in 2009. Now She Is Fixing How Teams Work.

Published on:
Sep 21, 2026
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Jennifer Dulski: Rising Team now is what we call an AI leadership and effectiveness personal trainer. Like taking a fitness trainer for your physical muscle and adapting it to your leadership and effectiveness muscle at work.Song: Built This Week, breaking it down. Built this week, we show you how. A fresh idea, a clever tweak you locked in. You built this week.Sam Nadler: Hey, everyone, and welcome to Built This Week, the podcast where we share what we're building, how we're building it, and what it means for the world of AI and startups. I'm Sam Nadler, cofounder here at Ryze Labs. And each and every week, I'm joined by my friend, business partner, and cohost, Jordan Metzner. How are doing today, Jordan?Jordan Metzner: Hey, Sam. Happy to be back. Nothing but excitement coming out of the AI news. I think since our last episode, like, five new models have dropped, so there's plenty to debate. Oh, and then, obviously, all the labs said that they were gonna stop advancing, so we've had that debate.And then, obviously, the president said, keep advancing. So, you know, no never a dull moment in the AI ecosphere, but even more excited for for today's guest.Sam Nadler: Yeah. We have a great guest. And before I introduce her, just really quick, if you haven't already, please don't forget to like and subscribe. We have new episodes every Friday. I think we're about to hit the 40,000 subscriber mark on YouTube, which we're all really excited about.And with that, I'd like to introduce our guest, Jen, with Rising Team. We'll dive into Rising Team. But, Jen, if you don't mind, give us a intro to who you are, where you came from, and and then we'll go into your your current business.Jennifer Dulski: Sure. Nice to be here with all of you. I'm Jen Dulsky. I'm the founder and CEO of Rising Team. We have that part of our name in common, and I come from a little bit of an a traditional, atypical background, to my to the world in tech, which is that I started my career as a high school teacher and the founder of a nonprofit to get help first gen students become first gen college graduates.And it is not typical for most of people I've worked with in big tech, but it it does come in handy, as it turns out, to have taught high school, and a lot of difficult, challenging teams are not that different from difficult, challenging teens, as I have found sometimes. And then I spent the next twenty five years working in tech. So I got into tech. My first ten years were at Yahoo back when Yahoo was the coolest thing on the internet, and then several years each at Google and Facebook, five years helping to run change.org, and yeah, a lot of experience, and it's really amazing the times we're in now. I mean, I've seen so much tech change and nothing like we're seeing right now.Sam Nadler: Totally. And I would love to get into Rising Team from a 30,000 foot level, but before we do, do you just mind showing us a little bit how it works?Jennifer Dulski: Sure. So the way to think about it, and maybe I'll share a few slides just to give you a sense of of what that of how that works, but maybe at the very highest level before I start jumping into it, my career so I spent most of my time as a division leader, which meant I, you know, ran big organizations, and I had a ton of support. I got human executive coaches, and I was sent to incredible trainings. And the problem was then when I came back to Teams of hundreds or sometimes thousands of people, I just didn't have anything that would scale. It was, like, too expensive, and we didn't have the bandwidth in our HR teams, and I knew there had to be a better way.And so in 2020, I spun off and decided to create Rising Team, bootstrapped by myself, and the idea was how do we scale high touch, really amazing support to people at all levels of an organization without having to do the actual really expensive high touch version of that. And what has come out of it, Rising Team now, is what we call an AI leadership and effectiveness personal trainer, It's like taking a fitness trainer for your physical muscle and, you know, adapting it to your leadership and effectiveness muscle at work.Sam Nadler: Super cool. And when you started this, AI didn't really exist. So was there, like, a different approach?Jennifer Dulski: Yeah. It was so interesting. So AI did exist. It just wasn't available to all of us. And I know this because my first startup, the DealMap, which I did not mention in my intro, was an AI company.In 2009, we ran an AI company where we did sentiment analysis and used natural language processing to analyze tens of millions of local reviews, and we actually built the models ourselves. Like, my whole team would stay up super late at night coding, like, big bill is bad, big burger is good, and training the models on how to how to learn that stuff. And ultimately, Google ended up buying that company, and, you know, those early pieces sit inside Google Maps now when you look at businesses, and it says, this place is casual and good for kids and so forth. So it's been around, and I knew in 2020 when I started this business that I wanted it to have an AI component. My original outline says personalized custom AI coach, but I couldn't really build it in 2020 the way we wanted to.So Rising Team actually originally started it more as software, particularly team building software. The idea was any team, any leader at any level could run a team building interactive session even remotely, so everyone's distributed without needing to hire an outside facilitator. And in 2122, when we were mid pandemic, that was urgently needed for most companies. And then in when all the LLMs launched, we were able to build this personal trainer AI layer on top. And what makes it amazing is that, you know, there are a lot of AI coaches on the market.The thing that we do that is hard to do is is the team building piece helps Arty, which is the name of our AI coach, understand your team. So instead of giving you generic advice, it can say, okay, you need to have a hard conversation with Tom. Tom really likes his feedback super straight on. Let me write you a script. Let me practice that conversation with you so it will land with Tom.Versus if I want to have a different conversation, you know, with Debbie, I can say, Debbie likes some encouragement with her feedback. Let's draft a script that's gonna work with her.Sam Nadler: Jen, I would love to see a demo.Jennifer Dulski: Okay. So one of the things that's been really interesting about this space is, you know, you guys talk about AI all the time, and we see how rapidly the technology is changing. The thing that most companies have missed is that it's not enough to just throw tools at people. And this summer, a ton of research came out from BCG and McKinsey and Gartner and everyone who says it actually isn't only about the algorithms, the models, and the tools we give people. It's about the people.And the BCG data says 70% of whether your AI transformation is successful or not lands on whether the people are able to adapt to these tools and still work with each other. And that's what we see is that the marketplace and the workplace is just so difficult right now because every company's drive to efficiency, intense pressure around adapting to AI. So you have all this intense pressure, this workplace tornado we talk about. The amazing thing is that the the science of high performing teams has not changed. So I also teach at the GSB at Stanford, and my class of what it takes to make a great leader is no different.I mean, it's different because now we use AI to help us, but the signs of high performing teams are still the same. People who can give and receive feedback well, who are clear on what's expected of them, who make people feel valued and appreciated. Every company also has their own sort of values and frameworks around that. The problem is that the tools up until we had AI are just not sufficient. Right?They're they're so periodic. And the way I think about it is so I I use sports analogies for a lot of things. I think about it if best in class leadership looks like some sports outcome, like running a triathlon. If I took a group of 30 people and said, I want you all to get to the same outcome, no one starts at the same point. Right?We have some good swimmers. I have some people who love to run and hate to swim, and yet what we do all the time is this. We take everybody, we put them in a single classroom, virtual or in person, we teach them all the same thing at the same time, and that's problematic because, a, they don't start at the same place, and, b, it doesn't get them out to practice with their team. So the way we thought about Rising Team is can we give people effectively a trainer that gets to know them, does an intake with them? And what we find is that we, as I said, we use these different modes to do that.So your trainer can coach you. It can do a working session, which is creating some deliverable, a script, a review, etcetera. It can role play with you voice to voice, and it can do these team building sessions. So what we have is a personal trainer who has these different modes that it can use with you depending on your need, what goal you're trying to solve, what challenge you're facing, and the system works together. So as you do more and more team building, it gets to know you, it personalizes its coaching to you and your team and your company, And then the amazing thing is that the business metrics move.So for me as an org leader, it wasn't enough to say, okay, are people am I going to give people a product and then they use it? Like, most products in my space measure success by whether people use it and whether they like it or not. And definitely that is true. People use it and they like it. The question is, does it move anything else?And we definitely see that in the numbers. So we see statistically significant lifts in manager effectiveness and employee engagement and eNPS and retention, how long people want to stay at their companies and how productive they are.Jordan Metzner: And obviously, like employee satisfaction and retention, you know, employees stay, they're usually pretty happy.Jennifer Dulski: Completely, and that's what drives all the ROI. It is so, so expensive to rehire and retrain employees, and right now it's very tempting for companies to say, it doesn't matter, because if people leave, we all know in this market, you know, 10,000 people are going to apply for their jobs because AI has made it so much easier. It's like the common app college, common app of workplace applications. But it regardless, sorting through, interviewing 10,000 applicants and retraining those people, it is a huge, huge time suck and money suck. And so boosting retention, we see between 1033% lift.So let me show you a little bit of the product, just a little teaser. So what it does is it gets to know me. Right? It starts by asking me questions about my experience, my, challenges, my goals, and so forth. And then the more it gets to know me, it also asks me about which company value I want to work on and so forth.And then it will summarize what it's learned and create a customized growth plan. Everyone in an organization gets a one of one growth plan. No, you know, not everybody in the same training, but my plan targeted to me, my particular one I got here is about leading through change, making my team feel valued, accelerating our AI adoption, etcetera. And then it breaks down each of those tracks into these different modes. So I might get a working session, a coaching session, a team building session in here, and the next thing it will do is schedule with me on my calendar, just like a trainer would.So finds a spot on my calendar, it schedules time, it sends reminders to me through messaging to show up. The other thing that happens is that I can go on demand anytime, and let me just show you an example here. So, if I have a particular conversation coming up that I need to practice for that might be a hard conversation, I don't have to wait for the trainer to bring that up with me. I can go ask Artie anytime, and the first thing that it will do is it will give me the people on my team. So this is, again, one way that having a tool like this is so different than a standard LLM because it already knows my team.Sam Nadler: Resumes don't tell you who someone is. Interviews do. Interviews that captures how someone thinks, how they communicate, how they solve problems at scale.Jordan Metzner: Awesome demo, John. What types of companies are finding success with Rising Team? I mean, whether it's kind of by company size or by company vertical, you know, where where has been the good fit?Jennifer Dulski: So one of the amazing things that you know how when I was explaining that this inside box of what great leadership looks like hasn't changed the science around it? The other thing that's true is that is true regardless of industry, company size, like if you imagine it, having a psychologically safe space and getting and giving feedback well and feeling appreciated are true whether you work at a giant company, nonprofit, a startup, school, and so we have organizations using Rising Team all throughout that mix. You know, we have big companies like Airbnb and HP and others. We also have startups. We have big non profits like the Blood Cancer United, formerly known as Leukemia Lymphoma Society.We have K through 12 school teachers and admins, like literally going in here to practice things like parent teacher conferences. So it's a really wide variety. Also, banks and, financial institutions, sometimes we see it used in really frontline orgs like bank branches and a lot of customer success, customer support organizations, essentially the places where it's hardest to get reach to. Right? Like the most under supported, the hardest to scale to, that's the place where we see the most most traction, and also the people for whom the soft skills don't always come as easily.So we have lots of big tech orgs, IT orgs, you know, those kinds of organizations, but it's quite varied.Jordan Metzner: Okay. We talked a little bit about kind of like what the customer view is, not the customer, but like the worker or teammate view. What is the executive team kind of able to yield from the tool?Jennifer Dulski: We are about to publish a piece called The Engagement Survey is Dying, and Here's What's Replacing It. Because, you know, engagement surveys, while they are valuable, they are so infrequent, maybe once or twice a year. And by the time you get the data back, it is unclear whether it's even relevant anymore because it took a couple months to analyze it and nobody knows what to do to action it. And so instead what happens is when you give people a tool like Arty, you know in real time what they are working on. So we can look at usage and satisfaction.We can also look at all the insights. So these are real insights, sample insights coming from big enterprise customers of ours. They're practicing things like, you know, promotion denial or underperformance or, you know, at at financial institutions, it's like the stress of of prepping for your licensing exams. All that is going in a rolled up, anonymized way to HR folks and the leaders at these big organizations. And the other thing that's happening is they can tell how people feel about it.At the end of every session with Arty and also every Teams session, we give a little survey that is a one out of 10 survey. We have an average of eight and a half and a median of nine across all our customers, and people are just saying things like, it's like you really know me. It's so easy to implement. It's different than what I would get if I typed into a general LLM, and so the team that is buying this and making sure it's working is also getting regular feedback.Jordan Metzner: The information is confidential. The attraction of that information becomes relevant to executives. So you're saying how many people are talking about asking about a raise, but you don't see Sally as asking about it.Jennifer Dulski: Exactly. A 100%. You would never see Sally. We can also slice it by things like level or location or function to get that those insights at a deeper level, but it will never be even at the team level. It would be much broader than that.And the other thing is privacy, and I'm sure this comes up in your news talks all the time, but the privacy elements are so important. So we start with a set of guardrails built into ARTI around things like protecting the EU AI Act. So ARTI will never help you make a firing, hiring, rating decision, as an example, and then each company can set their own stricter guardrails. So, you know, when we have financial services companies, they have a whole set of stricter guardrails where already will direct you back to your HR if you go into a direction you shouldn't.Jordan Metzner: That's great. Well, this was an awesome presentation, Jen. I think we should jump into the news.Sam Nadler: Let me queue you both up. IOS 27, I'm actually using Siri again. This is relevant because I have a lot of frustration with Siri. I haven't really used it with, the latest update. I also was complaining the other day.I have several nest hubs around my house, and I'm annoyed that they don't have Gemini yet. And I it's just like, you can ask basic things like the weather and to play Spotify, but, like, any real conversation, doesn't work. So I don't know. Have you guys used the new Siri, and why has it taken so long?Jennifer Dulski: I so I will tell you. I first of all, I'm a what they call a Zoogler, x x zoogler. You can actually see it right here. I have two phones. One is a Pixel and one is an iPhone, and I mainly keep my iPhone so I don't have the darn green bubble that people hate so much.You know, I read this article, and I probably have tried a bunch of Apple intelligence features without, knowing I have. I agree part of the issue is it took them so long to get to it that most people have other tools by now. But to me, the the big takeaway here is just AI is going to imbue every aspect of our life little by little, and some parts of that will be noticeable that we have to, like, pick up and actually try them, and others won't be noticeable, and those will be the best parts. It's like, you're what you want in your Nest Hub one day will just show up, and a lot of the Apple Intelligence things that I think are working the best are the ones that you don't have to turn on, that they just work for you when you're trying to do something else.Sam Nadler: Totally. Jordan, what's your thoughts?Jordan Metzner: I got two phones. I got two phones.Jennifer Dulski: Two phone club.Jordan Metzner: I know. Well, I'm I'm I guess I gotta wait for the Apple phone, then I'll have, like, know, two phones connected. I haven't upgraded to iOS 27. I'm on the beta, so I think I saw some, like, bubble on my phone to do it. And I have the Android phone.I think, like, you know, we're still far away from, like, any of these systems being, like, omnipotent and, like, always available. Kind of, like, when you ask the query to Google or even to ChatGPT, even with, like, better memory services now, it's not really in the same sense as if the conversation never ended and, like, you kinda pick up where you left off. If you say something, then it'll, like, go back and, like, pull some memory in on ChatGPT side. But yeah. I mean, I have Alexa devices too, and, like, those are also how, like, you know, poor intelligence.But you could see how like, I think, that we're gonna get to a level, and I think, you know, to your point, Jen, like AI is everywhere where, you know, it's just this conversation that kind of opens and closes, and like never opens and never closes, essentially.Jennifer Dulski: Can I ask a question? How do you feel about the memory piece? Because this is something also we're thinking about in our product. Like, if it if you ask it a question and it remembers a whole bunch of stuff you said before, is that helpful or creepy?Jordan Metzner: To me, that's helpful. Like, you know, I set my alarms every night before what I have to do in the morning. If they're not set, like, why doesn't it just ask me, like, hey, like, do you need your alarm set? Like, are you on at the same time as always? Or do you want me to make it earlier or later?Like, looks like you didn't set them today. Right? So, you know, there is some, like, AI ish right now that, like, you know, it'll, like, put your phone to sleep at nighttime and, like, some basic stuff like that. But it doesn't feel, like, sentient. Like, it doesn't feel like it knows enough about you to, like, do the things for you that make it more convenient because, like, end of the day, you just don't wanna miss your meetings the next day.Setting the alarm is, like, not hard, but remembering to set your alarm is, like, the hard part. Right?Sam Nadler: Awesome, guys. I think with that, let's wrap. Jen, it was such a pleasure to have you on today. Where can our listeners find you?Jennifer Dulski: So the website is risingteam.com, and I am at j dalsky on LinkedIn.Jordan Metzner: Awesome. Thanks, Jen. Thanks for joining us.Sam Nadler: Thanks, Jen. Bye, everyone.Jordan Metzner: Bye. See you soon.

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