How Rising Team Reached 55 Customers and 145% Net Dollar Retention in 2022 (Interview with CEO Jennifer Dulski)

Introduction and Company Overview

Nathan Latka

00:00Hey, folks. My guest today is Jennifer Dolesky. She's the CEO and founder of Rising Team, a SaaS company that helps organizational leaders build engaged, connected, and successful teams through authentic team development workshops around key leadership concepts. She's been leading teams for more than twenty years as an executive at both big tech companies and scaling startups, including Facebook, Google, Yahoo, and change.org. Her lifelong passion is centered around empowering people to reach their full potential. Follow along

00:25at risingteam.com. Jennifer, you ready to take us to the top? I am. Alright. So, hey, just cleared the air here for a second. Would you consider this more coaching, or is there a SaaS product you've built here, software?

SaaS Product vs. Coaching

Jennifer Dulski

00:36>> This is absolutely a SaaS product. In fact, there are no humans involved other than the leader of the team that uses our software. So, essentially, what we do is equip managers to run team development sessions with their teams by following the prompts in our software. It has everything from, you know, warm up to learning goals to an activity to countdown timers all in the software itself.

Nathan Latka

01:00Interesting. So what what's sort of the kind of thing that would happen where a leader at a company might use? Is it like a team retreat or the monthly all hands call?

Jennifer Dulski

01:06>> Or You can use it in any so we have teams all over the world using this. Sometimes they just set up dedicated time for these sessions. Sometimes they run them at off sites, you can do them remotely or in person. We have two different types of sessions. One are what we call learning kits, which are around all the topics that drive high performing teams like psychological safety and appreciation and so forth. Those sessions take about two

01:30>> hours, so you got to block a little bit of time for them, but we recommend once every six weeks. So two hours every six weeks is less than 1% of your time. And then the second type are what we call connection boosts. These are shorter, so one hour, and they're just, like, deeply understanding each other as human beings, and those can be done anytime.

Pricing Model and Session Types

Nathan Latka

01:50Okay. Very cool. Now how do you price for something like this? What's the average customer pay you per month to use it?

Jennifer Dulski

01:55>> Yeah. It's a subscription product. So you subscribe and then you get access to all the kits to use however often you want. We do have some bottom up sales, so individual managers. The pricing per team is $99 a month per team. So a team is a manager plus up to 10 people. And then most of our customers actually come in through kind of a top down mechanism where a head of a division or the head of

02:19>> people for a company will want to use Rising Team to increase engagement or scale their talent development. And those deals can be in the hundreds of thousands of dollars when you

02:29>> have How do you price those?

Nathan Latka

02:30The number of heads, head count?

Jennifer Dulski

02:32>> So we have two ways to price it. If it's sort of a partial org, we price it on number of teams. So, again, teams of up to up to lead plus 10, and the pricing goes down as you add more teams, obviously, and as you pay upfront. And then when you get to full org, we go to per employee per month pricing.

Nathan Latka

02:49Full org per okay. And how do you check that? What if someone says, no. This is just the the nine per I only need 10 seats, and I'm one lead. Just give me that $99 a month versus wait a second. That's your whole organization. You you should be on the bigger plan.

Jennifer Dulski

03:03>> Yeah. Well, we can tell how many employees exist at a certain company. So and it's actually way more affordable for them to go to the per employee per month. It's actually, you know, that's a better deal for everybody because you get unlimited teams. So you think about it when you're paying by team, let's say you want to do yourself and your direct reports, and then you want to run a second team with your cross functional project

Enterprise Pricing and Per-Seat Model

Jennifer Dulski

03:26>> folks, or you want to run just another session just to get to know people in the company. If you're paying by team, each one of those would be a separate team you pay for. When you get to per employee, you can do as many teams as you want mix and match.

Nathan Latka

03:38I see. Oh, what's going on there, YouTube? Good to see you guys. Now imagine this. You love watching these interviews with SaaS founders, but imagine if we all of the valuation data out from over 2,807 interviews I've done manually. Saves you a lot of time. Well, we've done this. We've built it into the beautiful interface inside of Founderpath. Check this out. I'll show you how you can access this in a second, but you log in, you

04:02connect your Stripe account, you see your valuation real time. You can see what it changed over the past eighty eight days and even set goals for valuation this year. Now the secret evaluation is there's many different ways to value a SaaS business. So the reason you're gonna see three or four different valuations inside of your Founderpath dashboard, this is all free by the way, is because depending on who's doing the buying of your SaaS company, you're

04:27gonna get a different valuation. A VC is gonna pay a different valuation, Private equity firm is different. If you're gonna do a minority sale, that's different. And if you sell the whole business, that's a different valuation. You can see all those when I hover over here, right? So the teal is what a VC would pay. Yellow is what private equity And red is if you sold the whole thing outright. Now what's cool about this is this

04:49is not built off random data. Again, you guys hear these interviews on YouTube. All these datas are built from real time valuation data points founder share with us on the show. So traction 1,200,000 seed round three point seven raise. They sold 22% of their business. Go in here and filter by the event. Maybe you only wanna see companies that have sold the whole business. Well, here are a bunch that have been acquired the valuation and the

05:13multiple. Maybe you're going out right now and you're raising your seed round. We'll go in here and look at all this recent seed deals that went down, what they raised, what valuation they raised at and what percent that they sold. There's never been a larger dataset of SaaS valuations than what you can get now inside of Founderpath. And we're thrilled to bring it to you. All right, we're gonna go back to the YouTube video here in

05:36a second, but if you wanna check this tool out, if you wanna jump in and sign up, you can check it out for free to get your valuation at this link. This link, founderpath.com/products/valuations. Or if you go to founderpath.com and hover over products, click on get your valuation here, and go ahead and sign up to give it a whirl. Again, all that valuation data live right inside the platform. I hope to see you there. Alright. Let's

06:02jump back into the interview. So on that full org model, you threw out, I think, several 100,000 per per year for that. Is that like your highest customer? Is that what you said, that's a fair average? Is, you know, a 100,000, $200,000 a year?

Jennifer Dulski

06:14>> It really depends on the size of the org. So, you know, if you're our per employee per month pricing ranges from kind of 6 to $10 per employee per month. So it's going to depend on the size of your org. Know, we have several That's

Nathan Latka

06:27what I was gonna say, that's what I'm trying to get a sense of. Are we talking thousand person orgs or 10,000 person orgs or 50 person orgs? Right? What's your sweet spot if you had to pick an average?

Jennifer Dulski

06:34>> Yeah. It's so funny. When we thought about our ICP, like who's our ideal customer profile, originally, we thought it's kind of mid sized, high growth tech companies, maybe someone with a low glass door score because what we do is actually really drive employee engagement and retention up. But as it turns out, all these really big companies wanted this too. What's happening in the workplace, as you know, it's just everything's changed. People are hybrid and everybody wants

07:03>> to quit and well-being is kind of down. And so, we have customers like the Bank of Hawaii and other kind of multi thousand person orgs. At the moment, like our average, if you had to take an average, it's probably you know, our average contract size right now is probably, like, $5,000 because we have a lot of people signing up on their own for a single team, and then we have a bunch of people, as I said, in

07:29>> the hundreds of thousands.

Nathan Latka

07:30That's 5,000 per month, 60,000 a year. Probably. Something like that.

Jennifer Dulski

07:35>> Although, again yeah. Sorry. Go ahead.

Nathan Latka

07:38What I was gonna say, would someone paying you 60,000 a year? How big is their team probably?

Jennifer Dulski

07:43>> So, again, the way to think about it maybe on average is a $100 per person per year.

Nathan Latka

07:51100 per person per year. Okay. Fair. Fair. Fair. Fair. And then the average team signing up with you might be something between, you know, a hundred and five hundred employees, something like that.

Jennifer Dulski

08:00>> You know, what I would say is it's real it really varies. So the the companies where we're signing full orgs, some of them are are, you know, 2,500, 5,000 people. And then sometimes what happens, usually organizations start with a pilot. So they might say, Okay, we'll start with 10 teams, see how it goes. Then they might expand to 100 teams. And then, you know, hope is that they will expand to all the teams in their org.

08:24>> So sometimes what we have right now are divisions of larger companies. You might have a 2,000 person division of a 50,000 person company, so I think there's a lot of upside for us there.

Nathan Latka

08:35Yeah. Yeah. Yeah. Well, and that would be a good way to reverse engineer your net dollar retention opportunity, right, is you're penetrated, but you haven't expanded yet. What's the expansion?

Net Dollar Retention and Expansion

Jennifer Dulski

08:44>> Right now, we're at a 145% net dollar retention so far.

Nathan Latka

08:49So That's amazing. Congrats. Help me let's put this on a timeline so folks can understand trajectory here. When did you write the first line of code for the platform?

Company Timeline and Bootstrapped Origins

Jennifer Dulski

08:57>> So I bootstrapped the company on my own for the first year 2020, and I actually worked with an agency and built a prototype and tested it with real people. We learned a lot from the prototype. Actually, first prototype was a tool that managers could use one on one with their employees. And what we learned is that it took too much time. People wanted less time and they wanted more team focus, especially in the pandemic era. And

09:27>> so we rebuilt the whole thing as a team based, you know, team development product that

Nathan Latka

09:32With the same agency?

Jennifer Dulski

09:34>> No. I hired a team. So I did. I bootstrapped, used an agency, built a prototype, tested it.

Nathan Latka

09:39Wait. Hold on. How much did you sink how much did you sink into the in the agency building MVP? Are we talking like $10,000 or like a $100,000? More?

Jennifer Dulski

09:46>> More like a 100. Yeah.

Nathan Latka

09:47Okay. Was that painful?

Jennifer Dulski

09:49>> It it actually wasn't because we were able to reuse a bunch of the things that we built and we learned so much that by the time I hired a team and we built the product, we kind of knew exactly where to aim it. So I feel like the learning was worth it. I don't know, maybe that's also having done, this is not my first startup. I you know, it wasn't like I was just throwing it in

10:12>> the toilet. I knew exactly what I wanted to find out. And I felt like I did learn that.

Nathan Latka

10:16Okay. So you learn. That's good. That's that's that's helpful. You learn, then you hire. Now are you still bootstrapped today or did you raise?

Seed Round and Cash Position

Jennifer Dulski

10:22>> We did raise. We raised a $3,000,000 seed round in February '21.

10:28K.

10:28>> And I am super scrappy with the funding. We still have about a million dollars left from that round. And, you know, now we're generating revenue, so we have quite low burn. And

Nathan Latka

10:38Are you profitable?

Jennifer Dulski

10:39>> Not yet, but we're not very off.

Nathan Latka

10:42Okay. I I

Jennifer Dulski

10:43>> see a a path to profitability here. And

Nathan Latka

10:46Now when you're saying not far off, you're Adam Neumann, you could be burning 5,000,000 a month, and you're not far off. For others, not far off is 10 k 10 k a like, you're plus or minus 10 k a month sorta deal.

Jennifer Dulski

10:56>> No. We're probably more like a 100 k a month.

Nathan Latka

10:59But Okay.

Jennifer Dulski

11:00>> Honestly, like, a few deals, and that is done. Right?

Nathan Latka

11:03So Does that make I mean, let's go back to the macro conditions right now. Right? If you've got a million in the bank, you're burning a $100,000 a month, that's you could say ten months of runway. Does that make you nervous right now?

Jennifer Dulski

11:13>> Not at all, actually, because we we actually got preempted for some additional funding, so we are taking a bit more money now. It's going get us another twenty four months of runway. We don't need a ton of money to get this thing, you know, to keep growing and get to profitability. So we took, you know, we're going to take the money when people came to us, some strategic folks that I think will be good to have

11:34>> on board.

Nathan Latka

11:35Less than 3,000,000 though?

Jennifer Dulski

11:37>> Yeah. Less.

Nathan Latka

11:38Okay. Got it. So, I mean, I'm you probably already answered this question because you said they're strategic, but right now would be like obviously a terrible time as a SaaS founder that's growing quickly to take money because evaluations are so compressed. But you just think these folks are so strategic. It's it's worth it.

Jennifer Dulski

11:51>> Yeah. And we're also we're doing it on a safe, so it has a higher cap, and I think that's reasonable.

Nathan Latka

11:58I see. Was the 3,000,000 seed capped or priced priced round?

Jennifer Dulski

12:00>> It was priced.

Nathan Latka

12:01Oh, interesting. So how does that work when you do a priced round? And usually it's the other way around. Right? You do a priced round, now you're gonna do a convertible note.

Jennifer Dulski

12:10>> I know. I mean, well, it's just we it made sense to do it this way this time and we have a better sense of where the valuation might go over time and people are comfortable putting a higher cap on it now. We have much more visibility, less risk.

Profitability and Burn Rate

Nathan Latka

12:25And way more traction, sounds like. Very cool. Most folks when they're raising seeds last year, you know, you're selling 15 to 20% in your seed. That's sort of standard. Were you sort of in that same range? Yeah. Okay. Fair. Fair. So you're talking like 15,000,000 ish valuations are in that range and you and the cap that you are now negotiating, you said is better terms than that. Yeah. Okay. Fair. Alright. Let's talk more about product, right,

12:49and sort of how the team is fueling the product. So how many folks total are on the team today?

Jennifer Dulski

12:53>> We have 11 full time people and about 16 if you count the part timers.

Nathan Latka

12:59Okay. And how many are engineers?

Jennifer Dulski

13:02>> We have five engineers and sort of two and a half designers. So I would count more than half the team as product development.

Nathan Latka

13:10Yeah. So what are the engineers working on? Is there any, you know, future products you can talk about or where you see the space going?

Jennifer Dulski

13:15>> Yeah. Actually, it's really exciting because what we're doing so we started by building the software. And again, like the way to think about it is traditional leadership development happens in one of two ways. There are what are called learning management systems. These are flat content like Udemy or LinkedIn Learning, where you're watching videos and you're kind of solo doing this learning by yourself. It is really low usage and pretty low satisfaction. And then the alternative is

13:42>> you hire these outside facilitators and they come in and everybody has a great time, but it's expensive, it's hard to scale, and it doesn't have a lot of follow-up built in. And so, what our software does is turn every manager into an interactive expert facilitator so you can get the interactivity but still have it be at the price of software. And the first version of the product, we were building the content. I've been doing this twenty

14:08>> years. I also teach two classes at the Business School at Stanford. I have all the access to the research on high performing teams. I started making some of the content. I hired two consultants, one on the DEI side, Derica Blackman, who's amazing, and we made our own content. The big idea and what we're working on now is platformizing the software so that anybody can create these interactive kits. And that means companies can too. So, they have

14:35>> their own philosophies about leadership development. Sometimes they want to use our content, but sometimes they want to use their own. But today, what they do is literally they'll like make a two page facilitator guide or something. And they give it to people, they have no idea whether it's used or whether it works. Now they can use our platform to create interactive sessions out of their own content, and that's going to be super effective and super sticky.

Nathan Latka

15:00And you mentioned you could go on in 2020 with the agency MVP, some test customers, and pilots. What about today? How many not not seats, but how many individual brands? Like, I think you said the Bank of Hawaii are you working with?

Customer Count and Expansion Potential

Jennifer Dulski

15:11>> We have 55 logos right now.

Nathan Latka

15:1455. Okay. Wow. And how much expand like, if you added no new customers over the next twelve months, how much additional revenue do think you can drive just into those 55 customers?

Jennifer Dulski

15:24>> Yeah. I think so I've I've run the pipeline. I think over twelve months, it's like a million and a half to 2,000,000. And over three years, it's like 15 to 20,000,000 just from the customers we have already.

Nathan Latka

15:37Yeah. That's a very cool math to run. Now can I take I I it sounds like you have massive ranges? Some companies have two seats or a team license at 99 a month. Others are 2,500 employees, and they're paying a $100 per employee per year. But can we take 55 logos times that ARPU of 5,000 a month? You're doing somewhere around $250,000 a month in revenue today?

Jennifer Dulski

15:57>> No. Not not quite yet. I would say we are

Nathan Latka

16:02Can you break it this year, you think?

Jennifer Dulski

16:05>> I think next year. Next year is when I would put that.

Nathan Latka

16:10Very cool. Well, again, it sounds like you have a very healthy motion for expanding accounts. Is that happening in a no touch fashion or as part of your 11 person team CS reps that actively drive that expansion?

Sales Motion and Demo Conversion

Jennifer Dulski

16:20>> Yeah. We have a basically three person sales/CS team that also includes me. And so we have we do do some hands on expansion work. Actually, most of the revenue upside, I think, comes from signing the deals and then expanding. Right now, we're converting 60% of demos to deals at some level. So quite on conversion on getting people to sign up at least for a pilot and where we need to put more attention is how do we

16:48>> get those pilots to larger rollouts. We're working with people on success plans. One of the things that's really helpful is we do pre post measurement before and after you start using Rising Team, and we can see that after just three sessions, 85% of the core engagement scores that we measure are moving in a significant way. So, almost every company out there measures engagement. What usually happens is like, you get the scores back, you have some gaps, and

17:16>> then you're like, Oh, what do we do? Let's start a task force or let's go back to the whiteboard. And it's really hard. And so what we're showing is we can actually not just measure it, but move it for you. And that's what's causing people to want to expand. So we're working on building these kind of success plans for people where we track and measure their movement.

Revenue Growth Trajectory

Nathan Latka

17:36And help me understand growth over the past twelve months. You got extra capital last year. Hopefully, you able to reinvest that back in growth. But if you're doing between, call it, a $100,000 and $150,000 a month today in revenue, what were you doing exactly a year ago, if if you remember?

Jennifer Dulski

17:49>> Yeah. So we're still we're actually under a little bit what you just said. I mean, a year ago, we were doing zero revenue.

Nathan Latka

17:54Okay. So it's like infinite revenue.

Jennifer Dulski

17:56>> Yes. The revenue, you know, started coming in in Q4 of last year, and then it grew a little bit in Q1. And then between Q1 and Q2, it, like, five x. Right? And between Q2 and Q3, it'll three x again probably.

Nathan Latka

18:11So we're we're Congrats then on breaking you in the past couple months. You broke the million dollar run rate. Congratulations on that. That's a big goal.

Jennifer Dulski

18:18>> Thank you.

Nathan Latka

18:19Very cool. Well, hey. Look. We're out of time. This is a fascinating story. Obviously, rooting for you. Let's wrap up here with the famous five. Number one, favorite business book.

Product Roadmap and Platformization

Jennifer Dulski

18:27>> My favorite business book is Gung Ho by Ken Blanchard and Sheldon Bowles. It's a story of what we can learn about business from a Native American folktale about animals.

Nathan Latka

18:39Wow. Number two, is there a CEO you're following or studying?

Jennifer Dulski

18:43>> I watch a lot of CEOs. One person I really admire is Brian Chesky from Airbnb. I think he's built a really impressive large business in a way that has a meaningful mission behind it. So for instance, the work they do housing refugees and so forth, I think it's a really powerful way to use your business for good.

Nathan Latka

19:02Number three, Jennifer, besides your own, what's your favorite online tool for building Rising Team?

Jennifer Dulski

19:09>> I'd say there's sort of internal and external. So the internal tool, I think we use the most that I like a lot is Figma. It's so easy to collaborate about how we're building the product. And the external one, I am a big LinkedIn fan. I'm a LinkedIn influencer. I write a lot about leadership. And so we get a lot of leads that way.

Nathan Latka

19:28That's great.

Growth Channels and LinkedIn Strategy

Nathan Latka

19:29Number four, how many hours of sleep do you get every night?

Jennifer Dulski

19:33>> I would say I aim for eight, and I might even stay in bed for eight hours, but I don't sleep all that time.

19:41>> Have a lot Fair things racing.

Nathan Latka

19:43Yeah. And what's your situation? Married, single, kiddos?

Jennifer Dulski

19:47>> I am married. I have two awesome daughters. They are all grown up. 22.

Nathan Latka

19:53Wow. Okay. You're super busy then. And then do you mind me asking how old you are?

Famous Five Rapid Fire

Jennifer Dulski

19:58>> I am 50 years old.

Nathan Latka

19:59Amazing. Okay. I

Jennifer Dulski

20:00>> just read a stat that founders in their fifties are, like, three times more likely to be successful than founders.

Nathan Latka

20:08I believe it. You have more you just have more experience in all of us. I get it. Take us home here. Last question. Something you wish you knew when you were 20.

Closing Advice and Wrap-Up

Jennifer Dulski

20:16>> Yeah. I think I wish I knew. And I spent a lot of time in my twenties thinking about what other people thought about me. And I wish I knew that everyone is too busy thinking about themselves to be thinking about me.

Nathan Latka

20:32That's a good one, guys. Risingteam.com, a more effective way to help all of your teams learn faster. They've signed up 55 logos to date, tens of thousands of seats, and folks using the platform already to date. Just broke the million dollar mark in terms of run rate, which we love, and pretty capital efficient. 3,000,000 raised on their seed. Still a lot of money in the bank with a path to profitability. Team of eleven, five engineers. There's

20:52a lot of tech behind this platform. Check it out. Risingteam.com. Jennifer, thanks for taking us to the top. Thanks so much, Nathan.

21:00One more thing before you go. We have a brand new show every Thursday at 1PM central. It's called Shark Tank for SaaS. We call it deal or bust. One founder comes on, three hungry buyers, they try and do a deal live and the founder shares back end dashboards, their expenses, their revenue, ARPU, CAC, LTV, you name it, they share it and the buyers try and make a deal live. It is fun to watch every Thursday 1PM

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