Jake Aaron Villarreal: I'm Jake Aaron Villarreal, born and raised in Silicon Valley. Here to take you behind the scenes to show what it's like to be a startup founder, the journey they're on, the problems they face, the products they build, in an effort to make our lives better. I'm excited to have with us today Jennifer Dulski, founder and CEO of Rising Team. Jennifer, welcome to the show.
Jennifer Dulski: Thanks for having me. Great to be here.
Jake Aaron Villarreal: Well, Jennifer, we had a chat a couple weeks back and always excited to understand what founders do and what inspires them to build what they build. Before we jump in here, where are you joining us from today?
Jennifer Dulski: I am in Palo Alto, California today.
Jake Aaron Villarreal: I'm there a lot. I'm from the Bay Area and oftentimes you can walk down a street and look in cafes, see multiple founders. It's funny because watching Silicon Valley, the TV show, was so funny because it was like all the people that we knew cameoed in that show. Yeah, it's really funny. I was there just a few weeks back and had a coffee with another founder and I was looking across the street and I saw the label of the company, of their company, uh, different founder's company on the building and that founder had been on our podcast. So, I had never actually met him. So, I ran across the street, I'm like, "Hold on one second," and said hello. And it was just, it was like every other building had multiple founders that we kind of knew. It was really fascinating. Proximity is power. So it's good to be in a, in a bay.
So let me if I can, before we jump in here about what you're building, just give the audience a little background of, of yourself, Jen. So Jen has been leading teams for more than 20 years as an executive at both big tech companies and scaled startups including Facebook, Google, Yahoo, and change.org. As a thought leader, Dulski writes about leadership and the future of work for LinkedIn influencers and teaches management as a lecturer at Stanford Graduate School of Business. Her first book, Purposeful, about how each of us can be movement starters, was published by Penguin Portfolio in 2018 and is a Wall Street Journal bestseller. Wow, I love your background.
Let's talk a little bit about your company. The company is Rising Team, which is an industry-leading team development platform that helps organizations increase employee engagement and scale talent development. So, really excited to jump into this. We're from the people side of the business. We help companies build, grow, scale. So, really excited to learn what you're building and how it's helping companies and how it's helping people. So, before we do that, uh, Jen, let's uh, talk a little bit about yourself. Give us kind of the, the 360 background of you. What experiences uh, helped kind of shape you into identifying what your company is doing today as an opportunity to really inspire to build it?
Jennifer Dulski: Yeah, I love this question. In fact, it is the first question I ask any candidates that I interview. I always say, "Tell me about how you became the person that I now see in your bio or on your LinkedIn page." And yeah, for me, if I think about like instrumental early experiences, one is that in high school and college, I was a coxswain on the rowing team, which [clears throat] people may or may not know what that job does. You see a lot of crew shells on like VC websites because they all want to talk about being a team. But the job of the coxswain is to coach the team, strategize the race, understand how to motivate each person uniquely. And it turns out that there's a lot of great leadership lessons in that job. And so my philosophy over time has become that great leaders are a lot like great coaches. Create clarity about what winning looks like, they find the best people and coach them to their highest potential, and they make the team feel like a team. So that is a core part of my early experience.
[Jennifer's Journey: From Coxswain to CEO]
And then I've been a founder since really my earliest days. Um, right out of college I founded a nonprofit. So started something from scratch right out of school and I also taught high school for four years while I ran this nonprofit, which is a little bit unusual for people who end up in tech. But for me it's always been about how do I create positive impact in the world? How do I amplify the voices of other people? And so I ended up in tech because I thought I could do that in a more exponential way. And as you noted, I've gone back and forth between startups and big companies, which I appreciate the ups and downs of each of those and I've learned a lot.
Jake Aaron Villarreal: Yeah. You know, I grew up in Silicon Valley and started at startups and ended up at Oracle for a number of years. And one of the things that I always learned was that the—and I was on the sales side—the best salespeople within the team that I was on were, and that was like comprised of 300 people, was it was always the educators. It was the, the, the school teachers that had moved on to become uh, in sales or a consultant and a lot of it was because they were able to simplify the message and present it in a way that people were able to understand it. And so what I learned there was that sales wasn't really selling or trying to influence someone to buy something. It was about educating them on what your product could do to help solve a problem they had. And it's not really Oracle didn't teach me that. I just observed it from others. It was my colleagues that taught me that. So being a teacher at high school and then running a nonprofit and being a leader, it seems like you got the perfect recipe to really lead and build a company, which is really cool to hear. This is really, you're the first guest out of 250 that's been on here that's really taught in school and then gone on to become an innovator.
Jennifer Dulski: It's, it's pretty unusual. I do think the other thing you learn as a teacher, well you learn a couple other things. One is um, as you said it's both about clarifying the message, but it's also about understanding where each person is starting from. Everybody has different styles of how they learn, how they understand, what they react to. And when you're going out and building a, a company, you have to understand where people's starting point is because your solution will only work if it matches someone's real needs. And so a lot of it is understanding their pain and understanding their own personal style helps you craft something.
And companies work if you find enough pattern recognition, right? Like actually the first version of Rising Team, I, I was planning on... I interviewed before I started the company. I interviewed a bunch of people about the potential idea and the very first version, everybody loved it, but they all wanted something slightly different and I just realized it wasn't going to work. It was just too bespoke. I couldn't build it at scale if everybody wanted something slightly different. And so it took me having enough of those conversations to find the patterns of people who wanted and needed the same thing that made it company-worthy. And now it's so interesting. Even though we offer a lot of customization at Rising Team, the vast majority of customers who use our products do not customize it. They use the core product we offer for leadership development and team building, the same one at Google, at Hershey, at the Massachusetts State Probation Office, because it turns out that building high performing teams is very similar regardless of what kind of organization you work in.
Jake Aaron Villarreal: Yeah, I love that pattern recognition. Pattern recognition seems to be the path of most successful companies and people. But it's not just recognizing the patterns. It's also executing on implementing those patterns and then also going from looking at the patterns to becoming a pattern creator where you're actually creating and innovating.
Jennifer Dulski: Yes, I think it's something that's overlooked in building anything where you don't necessarily think about it. You just kind of fall into how you operate. But I think to be more intentful around it can really help save a lot of time and money and effort in getting to where you want to go.
Jake Aaron Villarreal: That's true.
Jennifer Dulski: Also, having worked in tech for so long, I've seen um you know, sometimes even when you recognize the pattern, you don't always build the right thing, the right solution for it on the first go. I've been through that myself many times. And sometimes there's also a sort of market timing and readiness for the things you're building. I've seen so that the pattern recognition matters, the execution matters, and the timing matters.
Jake Aaron Villarreal: Yeah. Well, I want to jump into your company, but there's other questions I want to ask before we get there about your background. So, you know, you joined Yahoo really before it was Yahoo that everyone knows about today. And in that, there was a lot of growth there. It was early days. What did that era teach you about scaling before anyone had a playbook?
Jennifer Dulski: It was incredible. I have to say it was just so energizing to work there in those days. And in fact, when I first started at Yahoo, they gave us as a new employee, they gave you a little license plate holder that said, "Do you Yahoo?" Some people will not be old enough to remember those, but those of us who do, they were all around the valley. And I didn't actually put it on my car because I thought it was too show-offy. It was like so cool to work there that I felt like, "Oh my god, people are going to be so jealous of me if I put this on my car," that it was like bragging too much. Um, so it, it was just, it was kind of like on fire. The people were so interesting. Everything we built worked, you know, it was sort of just the glory days.
And then I, you know, I stayed at Yahoo 10 years. So I learned a lot about, as you said, scaling. And I guess I would say my major lessons, the first one is really pay attention to the people. Like at the end of the day, our careers are largely about the people that we build relationships with. And that's true when you're working with them. So, you know, building really strong relationships with the people I worked with made work better every day. And also those people went on to do amazing things. Like I saw on your podcast a while ago, you know, he's a friend of mine from my early Yahoo days and then went on to start Cloudera. And you know, Ryan Roslansky, who was like a PM with me in the early days is now the CEO of LinkedIn. Like it's incredible what the people, if you invest in them, go on to do and what, how you can help each other.
[Lessons from Yahoo: Scaling and Focus]
The second thing I would say is I really did learn the power of focus because in the very early days we didn't, right, we built everything. It was like, "Oh my god, we can do sports and we can do finance and we can have mail and we can have everything," and everything worked. And then um, as time went on, it just became clear that we were doing too much and it's harder to narrow down later because you know everything was a sort of sizable business. And so it became just really important later on to think about where to put our resources and how to invest, double down on the things that were really high potential and maybe spend less time on the others. And Yahoo went through some difficult time periods in the later years trying to figure that out. And it's actually really cool to see kind of a resurgence of Yahoo again.
Jake Aaron Villarreal: Yeah, I'm seeing it. I use it on a daily basis to look at like the news and finance. And I didn't really think about it was kind of, it was like the company to be at during the dotcom boom. And I mean I remember joining Oracle and looking across my network of friends and a few joined Yahoo at the same time, and I was thinking, I want the big enterprise experience so I understand how businesses operate and systems integrate. And he was like, "I'm going to go sell ads," and I'm like, "I don't know if that's something I want to do." And then you know fast forward like I think it was 12 months later, he's like, "Dude, I'm worth 13 million in stock," and I was like sitting there making 60 grand a year going, um, did I make the wrong decision? [laughter]
Jennifer Dulski: Yeah, I mean there, you know, and that stock may have been worth more or less as time went on, but right, you know, when I, I joined Yahoo straight out of business school. I was an MBA intern at Yahoo, actually, one of the first two ever MBA interns. And wow, when I joined the company, it was only 400 people. And so really was a startup, but most of my friends from business school thought I was nuts, right? Because I had offers at McKinsey and, you know, P&G and so forth. Then my Yahoo offer paid half as much. Not, not just a little bit less. It paid half. But I just couldn't wait to do it. I was very, you know, I was very lucky, I will acknowledge, because I had a fellowship to business school, so I didn't have a debt coming out and I could take a salary that was half as much. But yeah, it turned out to be a great decision and really impacted the rest of my career.
Jake Aaron Villarreal: Yeah. Well, you transitioned and you ended up at Google where they pay a lot of money, but you decided to, to leave and to join change.org. How was that decision made?
Jennifer Dulski: Yeah. Well, I guess first of all, the way that I got to Google, when I, I left Yahoo to go do my first zero to one startup. Um, and I spent four years at that company, which failed four times in four years. It was just like a lesson in extreme failure. Um, but we just kept going. I used to call myself "too stubborn to fail." It was like during the days when the banks were too big to fail, I was just too stubborn. And we, the fourth thing we built ultimately ended up being really successful and we sold it to Google. So I ended up at Google through an acquisition of a startup. And um, you know, I really enjoyed working at Google and I wasn't looking to leave.
Um, and then I got this call about a job to be President and COO of change.org. And part of the way I make decisions, I have a tool that I developed actually in my Yahoo days, I call it the Motivators Chart. And it actually started it because a woman on my team once said to me, "You know, if I ever do anything [snorts] good and you want to appreciate me, just pay me more money, like a spot bonus, a gift card." She's like, "I don't care about any of this recognition stuff." And I was very taken back by that at first. And I thought that was kind of crass that she told me that. But then the more I thought about it, the more I realized it was actually really a gift that she told me, because if she didn't, then I would have just kept going doing the things that I liked. And for me, as an example, my favorite type of appreciation is a handwritten note. Okay? So, you know, I love a good handwritten note, but can you imagine if the woman on my team who's like, "Please drop me a spot bonus," gets a handwritten note, like maybe she would appreciate it, but probably not.
And so I started this exercise with my team where I give them an empty circle and I just say, "Tell me all the things that motivate you. You can make them as big a pie slice as you'd like and then color code them red, yellow, or green based on how you're feeling about those things right now." And I do it with my whole team maybe once every six months or so because it really helps me understand what's driving them. And it also gives me very early notice if there's any red flags. Like the retention on my team is very high because I know well in advance if someone's thinking about leaving or unhappy about something. And now we have the Motivators Chart productized in Rising Team. So it's scaled to, you know, tens of thousands of teams.
But I also use it for myself. This is a long-winded answer of saying like why did I leave Google? Because whether I'm, it was on paper or in my head, I had my own kind of Motivators Chart. And at that time in my life, the biggest slice was impact. I just really wanted to do something that I felt was going to move the world in a positive direction. And the chance to help lead and scale change.org just doesn't come by every day.
Jake Aaron Villarreal: Mhm.
Jennifer Dulski: And in fact, I called Rob Solomon, who is a friend of mine from Yahoo days, who's also the founder of SideStep and later former CEO of GoFundMe. And he, I called him for advice and he said, "You know, Jen, I've been," he had just sold SideStep to TripAdvisor and one of the other travel sites, and he said, "I've been looking for jobs like this and there just aren't that many of them." And I was like, "Okay, that, that pushed me towards it."
[Transitioning from Google to Change.org]
And then I had a call with my mother, and my mother said, "What are you doing? Why would you take this job? You have this like milestone-based financial reward on the table at Google." I was 18 months into what was a three-year annual retention bonus.
Jake Aaron Villarreal: Wow. So, you left some money on the table.
Jennifer Dulski: I didn't even have, I didn't even hit the two-year mark. And she's like, "Just stay. It's only 18 months more." And I could hear myself trying to convince her on the phone why I thought I should leave and take the job. And then I hung up the phone and I said, "I guess I really want that job." Because I could just hear it in my own conversation with her. So now when I talk to my students and they're trying to decide between multiple job opportunities, that is one of the techniques I teach them, is go talk to someone you trust and listen to yourself and see what you're saying.
Jake Aaron Villarreal: Yeah, I like that. I also like that decision-making tool you created because we always, we have a decision tool that we use as well, but when it comes to your employees, like to get them to explain what motivates them today, what they're happy about, what they're not happy about, what they want to become. Like, I don't think managers do a good enough job of asking those questions, and that's where you see them leave the company. Like you're talking about retention where you, high where you're at. Sometimes it might be fear that you know your employees are unhappy. You don't want to ask them how you... because they're going to say, "I kind of want to go," or "I need more money," or "I don't like what I do." And then you got to make another decision. Um, but at least you know what you're dealing with versus you get an email with a two week notice. You're like, "That's right." And then it's too late.
Jennifer Dulski: Um, so even if you, I mean the motivator chart is a great tool. And then the other thing to think about is like, think about each of your employees every six months or so and say, "How would I feel if they walked into my office and quit tomorrow?" And a) if you feel okay, they're probably not the right person for the role anyway. And if you would be upset, then you need to be reaching out to them to find out how they're feeling because you don't want that surprise, "I'm two week notice." And yeah, in Rising Team, I know we haven't really talked about it yet, but we, the motivator chart is only one assessment. There's all sorts of things. Like, I know about each person on my team. I know exactly how they want to be appreciated. I know what they feel like their natural talents are that make them jump out of bed. I know their long-term career goals through a Career Horizons exercise we have. So it is true as most managers don't do this because they don't have the tools to do it and it's hard to put that stuff together on your own. Now we're in a blessed age of software and AI that makes it a lot easier.
Jake Aaron Villarreal: Yeah. Let's jump into a Rising Team. So, you know, what was the main thesis that you saw that you felt, here's a problem that we could solve with technology and here's why.
Jennifer Dulski: Yeah. So, originally when I first started it, it, it was born out of my own pain as a leader. So, as I said, when I started at Yahoo, it was only 400 people and I was not a manager. By the time I left, my team was bigger than the whole company was when I started. And wow, I had a lot of support as an executive, right? I had my own executive coaches. I was sent to trainings with people like Fred Kofman and [clears throat] Ken Blanchard and Verne Harnish, like incredible. And I had no way to scale that out to my team. So I would get back to my team after going to these amazing trainings. And the first thing is I say it was like being taught to fish and going back to the lake with a binder. Like I had no fishing pole. I had nothing to do to even translate what I had learned to my own direct team, much less scale it out to the managers that worked for me. Hundreds of managers, you know, were like begging me for support and guidance. And it was just too expensive. I could not afford to give them what I was getting.
And then the other thing that was happening is almost all big companies track these engagement surveys or pulse surveys or Googlegeist or whatever you want to call it. And I would get these surveys back and some things would be good and some things would be bad. And then it was my job and my managers' job to come up with a way to action these surveys. And I never knew what to do. It was like every time, back to the whiteboard, I need a new tiger team. And I didn't know even with all the time we spent on it whether anything would work. And so basically I said, what if we could give every manager the same tools and support that executives get for a much more affordable price? Now we do it at 1% of the cost of what executives get. And that was first enabled by software and then now enabled by AI.
The way I sometimes describe it to people: imagine, here's the other problem with the way we train leaders today, is even the junior managers when they get training, they're put in cohorts together, like in a room, virtual or in person, and they're all taught the exact same thing at the same time. So, if I were trying to train a group, let's say, here's a question for you. Do you like to swim, bike, or run?
Jake Aaron Villarreal: Yes, I like to swim and run.
Jennifer Dulski: You like to swim and run, but not so much bike. Okay. So, I um also like to run. I really am not a good swimmer at all. If we hired a personal trainer to train, let's say we're both going to prepare for a triathlon. You know, you and I would, if we had a trainer, they would do different things with us. We'd have a different plan. It would be customized to our needs. We both want the same outcome, but we're not going to do the same thing to get there. That is essentially what we now build at Rising Team. We call it Leadership Personal Trainer. And it's essentially customized to each manager based on their starting point. It helps them develop a plan, practice that plan, roleplay hard conversations, and then run synchronous sessions with their team to get in there and practice in the water, on the road like you would, you know, for any thing you were training for on the fitness side.
Jake Aaron Villarreal: Wow, that's really powerful. When you look at a company, you've been at smaller startups and enterprise companies. You mentioned that you felt middle managers were the most underinvested roles in companies.
Jennifer Dulski: Yeah, it is.
Jake Aaron Villarreal: Walk through that.
Jennifer Dulski: Yeah, it's so true. I, you know, as I said, executives get a lot of support and so much budget put towards them because not only is it executive coaches, they can bring in human, you know, facilitators anytime they want to do a team building thing. They have budgets to fly and meet each other around the world. Entry-level managers sometimes also get support. Not every company, but many companies have like a new manager training program that they will put people. Middle managers are like the forgotten folks inside companies. And so, not only do they not get support or training, they also have more pressure and stress than any other level of manager because right now we're also in, in what's called 'the great flattening', right?
[Empowering Middle Managers: The Overlooked Heroes]
A lot of companies have a huge pressure for efficiency, cost savings, productivity with AI, and so they're removing a lot of that middle management layer, which means the ones who are left are more overwhelmed and burned out than ever. They have bigger teams. They have less training, and so they need the most support. And as I said, the great news is now we can finally afford and to support them not only a little bit, but actually as good or maybe even better than what executives get.
Jake Aaron Villarreal: Wow. I love that. Yeah. We've seen lots of companies like a Salesforce will bring in a Tony Robbins who will go in and present to the whole, you know, company and then everyone that's not there can log on and watch it and it's great. And I'm sure that Benioff has got one-on-ones with Tony or maybe he did in the past.
Jennifer Dulski: Yeah.
Jake Aaron Villarreal: The middle management or anyone else might not get that. You know, if it's a million dollars an hour, you're probably not going to get it.
Jennifer Dulski: So, like, sure. And even if you get to watch the video, that's the fishing pole problem, right? You go back to your team and you're like, "I just learned a lot." Like I had Verne Harnish, who wrote the Rockefeller Habits, one of my favorite business books. I loved it. He said, you need to do a one-page plan with your team. And then I went back and I had to figure out how to do that myself. You know, it was, there were no guided tools to help me, you know, get in the water and practice it. You know, the other thing that's been interesting is, and the reason we use "personal trainer" as a metaphor rather than "coach" is because if you think about what happens with executive coaches, they are trained to pull the answers out of their client, right? A lot of my friends are now coaches and the premise is your client already has all the resources they need to solve these problems and so you're doing a lot of like, asking the right questions and so forth. That works great with executives who have a lot of experience. If what you're talking about is a new or middle manager who has two or three years of experience, no matter how many questions you ask them, they are not going to come up with the right answer because they've never had the training. Right? They need someone to say, "This is what a good push-up looks like. Now do 20." Right? Like, not "What do you think a good push-up would be, and what would be the, you know, if you had a magic wand what would your push-up look like?" So this is why we are like, let's start with the idea of a personal leadership trainer and help them understand what great looks like and then practice it.
Jake Aaron Villarreal: Yeah. So, if you're a middle manager out there or really anybody out there that thinks this could be a good platform or tool to use, like what's the actual user experience getting? Are they just logging into a website and putting content in and having some like AI assistant talk to them or put them through exercise? Like what's the...
Jennifer Dulski: Yeah. So, there's basically three, there's three modes if you think about it. So the first one, the trainer itself is going to do some kind of intake with you, right? We'll say, "Let me learn a little bit about you so I know what kind of a growth plan you need." And it is a chat-based experience. It'll ask you questions, you'll answer them, it'll say, "Now here's your, here's your plan." It has some tracks, it has some steps. The steps themselves are, there are sort of three types. One is a working session with your coach. So that would be, let's say you're trying to develop goals, really good, you know, OKRs, or you're trying to create a great one-on-one agenda for your team. You're doing a working session with that coach. It knows a lot about you already. And in a minute, I'll explain, it also knows about your team, and so it can help you get to that outcome you want.
The second type of activity you might do is a role play. So, you know, I teach at the business school at Stanford. My class is 100% roleplay based. We take really hard cases.
Jake Aaron Villarreal: Wow.
Jennifer Dulski: Based on CEOs. Like I actually, we write cases about CEOs and then invite them into class as the guest. And the students have to roleplay as if they were that person trying to handle the hard situations from the case in front of the whole class and in front of the guest. It's actually...
Jake Aaron Villarreal: Wow, mortifying. Honestly, I'm glad I didn't have to take the class [laughter] myself.
Jennifer Dulski: Um, but the role play, the practicing of hard conversations is really important. And if you think about the day-to-day conversations that managers need to have around things like, "Are you or are you not getting promoted?" "How do I give you constructive feedback on something?" "Someone wants to ask their manager for career advice. How do I guide you?" The second type of activity people do within our product is these practice conversations. You go in, you practice with a live partner, voice to voice. You can pause, get coaching in the middle, you get scored at the end, you get suggestions about how your phrasing could be better, things that worked well, things that didn't. That's the second type.
And then the third is what we call "team session." So, it's not enough to be a manager and just practice on your own with AI. At the end of the day, you have to get out with your team and really bring these things to life with the team. And so we have built more than a hundred what we call kits that help managers run interactive sessions with their teams. Some of them are on topics like the motivator chart. So you might have everybody fill out their charts and talk about it with each other. Some of them are more um, connection-based. Like, "I'm just trying to understand you as a human," like the question you asked me, "What life experiences shaped you?" The more teams know about each other, the less conflict there is, the more they feel valued and stay at work. And so we guide managers to have these interactive sessions, you know, a few times a quarter.
And then the AI coach learns everything about the team that they're sharing in these sessions. So when you go to roleplay, you actually pick a specific person on your team. And you might say, "Hey, I need to tell Susan she's not going to get promoted." And it says, "Okay, I will act as Susan who sometimes gets a bit defensive and likes her feedback straight on and so and so." And it has those insights about the person as you interact with your, with your trainer and coach.
Jake Aaron Villarreal: Wow. So, is that trainer and coach an AI?
Jennifer Dulski: Yeah, it's an AI.
Jake Aaron Villarreal: Got it. And in the second step, you said then you'll be with a live, like other person you're talking with. Is that also an AI or is that...
Jennifer Dulski: Okay. So all this is you and AI within the platform, and, and then you and your team. So there is a human to human piece that is you and your team guided by software.
Jake Aaron Villarreal: Yeah. Cool.
Jennifer Dulski: And that's why it's so affordable, right? Like you can do this, as I said, like 1% of what it would cost you to have a team building and an executive coach and so forth.
Jake Aaron Villarreal: Yeah. That's amazing. I got to bring this up to my executive coach because I do have one too.
Jennifer Dulski: And executive coaches are great. Like I am, I am not dinging them at all. It's just you can't, you know, if you're a company of 20,000 people and you have, you know, 3,000 managers, you just can't hire an executive coach for all of them. And there was a trend towards virtual coaches. Even that was too expensive to get to every manager. And also, you know, they're hit or miss. Like you can get some great coaches and you can get some less than great coaches. Here, every coach is personalized, customized to what the company cares about and gets to know your team over time, right?
Jake Aaron Villarreal: Yeah. I love that. Really cool. You know, I'm also really interested about when, kind of going back to your education and being a high school teacher, but also being a teacher at Stanford. What has that experience taught you? And how do you rethink what you thought you already knew before you began teaching?
Jennifer Dulski: My gosh. Well, I will say in general that teaching always makes me better at what I'm trying to do. So, I first came to that realization when I was teaching in the summers at a program called the Breakthrough Collaborative, which is the same program I started in, I started the Pittsburgh site of that program. But in the summers, I would have, I was teaching fifth graders how to actually, not fifth graders, I was teaching rising seventh graders how to write a five paragraph essay. And all summer I was grading these essays and structuring them. And then when I went back to college, I did this in the, in the summers during college. Oh my god, I aced all my classes just because I knew how to write a really good, clear five paragraph essay, which is basically all college was at the end of the day. So I've known that for a long time.
[Teaching and Learning: The Impact of Education]
That is also definitely true of my teaching at Stanford. So I teach this class called "Managing Growing Enterprises". It's a second-year class. It's all about how to scale companies and it's about best practices on things like hiring and onboarding and conflicts and managing boards and if you have to letting people go and all of those things. And I am so much better at it in my job because I teach it. And also I believe, hope that I am a better teacher because I do this in the day-to-day so I can bring in real stories. And one example would be um, hiring. So, you know, there's like, I have made lots of mistakes over the years of hiring people who just weren't the right fit for the job, etc. In class, I teach a method based on the book Who that was written... I'm sure you've read this. Well, you work in this space. Obviously, you know this space super well. And we talk about how to create a really good hiring scorecard, how to do interviews against that scorecard, how to be really great at checking references. And so I can't teach that in class and then not use it at our company. So we have a super robust, even for a very small startup, you know, tight hiring process. And when we stick to it, our hit rate is very high.
Jake Aaron Villarreal: Yeah. You know, we've had so many guests on this podcast and a lot of them are challenged as they build their companies to find the right people and to do it, you know, at a pace that they need. They get investment and there, the clock is ticking to build and grow. And you know, sometimes you pull the trigger too quick and you get it wrong and it sets you back. And so you want to figure out how you can do it right. We have a lot of different philosophies of how we operate and how we make sure we get it right for our, for our clients. But what's one or two things that you can share with all the other founders that are listening that they can take with them as they're looking to hire on their own?
[Hiring Strategies: The Importance of Scorecards]
Jennifer Dulski: So I would say the number one thing, as I mentioned before, is creating a clear scorecard of what you want in the role, and the scorecard has two elements. The first is outcomes and the second is attributes. So by outcomes I mean not what experience does the person have, but rather what, if you were to write their OKRs, what would you expect them to deliver? So for instance, if you're hiring a salesperson, an outcome might be, you know, "reliably deliver against a million dollar plus quota." And if you have a list of outcomes, you can then interview people against those outcomes to make sure that they are capable and have in the past been able to do those things.
I, for instance, don't hire specifically only people who've done the job before because sometimes there are other ways to demonstrate you can hit those outcomes. So, as an example, when I hired a Chief of Staff, I had six final candidates, three had been Chiefs of Staff before and three hadn't. But against the scorecard, it was quite clear that in their other jobs, whether it was product manager or whatever, that they, they could reliably deliver the outcomes I was looking for.
And then the attributes piece is more like values. How are they going to behave, fit with your, within your company's values? Because at the end of the day, people, the rule, my rule and generally the rule for most companies is you only need to do two things to be successful inside any organization. One is deliver the results that were asked of you, and two is live by the values of the company. That's it. And it's interesting where people fail is one or the other. Some people really nail their results. They're just every, beating every goal, but they don't treat other people well. And you cannot leave those people in your organization because they're really toxic and it's hard, and oftentimes people do not fire them and then they cause havoc in your organization. The other side is also true. Some people are the nicest, most values-aligned people ever and they don't hit their results, and you also cannot leave those people. So what you want to hire for is people who will do both, hit the results and align by the values.
And then the other thing I would say, it's interesting. There's actually... the reason I teach this class is because there's a case about me. So I started going as a guest when I was working at change.org. And my case, one of the vignettes in it is about checking references. And it is shocking to me how bad most people are at checking references. And so we really drill it in, in class. And we have a very structured way of doing it at Rising Team also, to ensure that we get as unbiased, clear answers from references as possible, and that's extremely helpful.
Jake Aaron Villarreal: That's a really big topic. I want to dive a little bit deeper on that reference checking because let's be honest, most of the references that you get from your candidates are people that like them, are going to talk great about them, are going to try and help them get that job even if they don't really have what it takes. But your job as a hiring manager or leader of a company is to understand what you're hearing and somehow get value out of it knowing that maybe that's not what you're trying to get. So walk through the process of to really check a good reference and get the value out of it.
Jennifer Dulski: Yes. So the first thing you start with is who you talk to. So ideally, and I have a two-by-two for this we show in class. Ideally, you want people who have a good amount of information, meaning they've worked closely with the person, and unbiased information. So, they aren't, you know, BFF, or the, the other day I talked to someone who checked a reference on someone and then only later found out it was the person's husband.
Jake Aaron Villarreal: Wow.
Jennifer Dulski: And had never been told.
Jake Aaron Villarreal: [laughter] That's not good. You know, talk about bias in a reference.
[Effective Reference Checking: Getting the Real Story]
Jennifer Dulski: Yeah. So ideally, you're checking both the references that they give to you and some back channel references. Although the rule is never from their current company. You can check a back channel reference, but it needs to be not where they currently work. Then once you have the group of people you're talking to, the key is to ask very structured, pointed questions. So, our reference check typically starts with explaining the role and then going through the scorecard elements one by one and asking the reference to rate the person on a scale of 1 to 10 against that item. And if they know there's a lot of items, they may not give them, you know, a nine or 10 on everything because no one is really a nine or 10 on everything. And that allows you to peel. And you can even start by saying, "Hey, we know no one's a nine or 10 on everything. So just..." and that gives them the permission to say "Here's where they're really strong, and here's where they're not" without having to ask them directly. And then you can see against your scorecard which things matter most, and are they scoring high there.
Then I ask questions like, I have what I call the three Ps. How did they perform versus plan? So versus goals they set. How did they perform versus their peers? So if you had to rank them against all people that you've worked with in this function, would they be, you know, top 10%, top 20%? They'll give them a ranking. And then how did they perform versus the prior period? So are they growing over time, delivering more over time? And then I always, always end with, "Would you hire this person again?" And it is incredible references people have given me who should be their absolute best references. Sometimes I get answers like, sometimes I get answers like, "Absolutely, in a heartbeat." In fact, you know, I've been told, "I hope I get to hire them back from you." I've been told, "I... when they called me for the reference, I thought they might be, you know, interested in working with me again." Like really, really positive things. And I've also been told, "Well, it depends. I would hire them for a certain role that looks like this," or you know, those kind of very wishy-washy answers. And so if you ask the right questions, you really can always peel apart the data in a way that's helpful.
Jake Aaron Villarreal: Yeah, I love that. Well, we're a big fan of that book you mentioned, Who, and also just, you know, the process of the reference checks. We, we do that as well and it's very powerful. It's something that we also train our own clients like "this is how you should do it and here's why you should do it." So, it's been really, really helpful. God, it's so, so, so quickly this time has gone. It's already been almost an hour here and I, I have like a thousand more questions to ask you, but I want to make respectful time and use of the audience as well. Rising Team, if you're out there and wanted to use it, talk a little bit about how long it takes to get up to speed with it. Is it a super high-end budget we got to allocate for? Like, how easy is it to get up with? And what am I looking at?
Jennifer Dulski: It is incredibly easy. Like there is, first of all, we provide all the training for managers and it just takes one training on how to use the platform and then you're up and running. Like, it...
Jake Aaron Villarreal: That's great.
Jennifer Dulski: And for companies to use it, you know, at the enterprise scale, there's a little bit of back and forth on things like security and building single sign-on and so forth. But then once they have that up, it's like you can onboard every manager all at once, they're all running. And the other thing that I think is really important is measuring whether it works, right? Like a lot of the tools in our space often measure value by usage. They just say like, "Well, people use it a lot or they don't." We really care about whether it's going to move the numbers that companies care about. And so we now have many years of data to show that it boosts employee retention. People, top talent stays longer at their companies when they use this. It boosts engagement, employee net promoter score. Like my company has eNPS of 100. I don't have any detractors. It's yeah, it's pretty amazing.
We also see movement in manager effectiveness scores. We even see movement in productivity metrics like the number of issues resolved by customer support or IT teams. Because when people feel valued and supported at work, they stay longer, work harder, all the things you would want to have happen. And it is both easy to start and also not expensive. You know, the pricing varies by the volume of the customer, but as I said, it's kind of that 1% of the executive coaching cost range. So, it's not a huge budget for...
Jake Aaron Villarreal: Got it. That's great. I want to ask you one last question. If you were to start this journey over again with Rising Team, what would you have done differently when you began?
Jennifer Dulski: Well, I've learned really two things in the, in the Rising Team journey. And the, first of all, this is not my first startup. So I, you know, the good news is I make different mistakes now. I, you know, I don't make zero mistakes, but I try not to make the same mistakes twice. This is however my first enterprise company. I... most of my companies have been B2C and this is the first real B2B company. And so the two things that have become clear to me, one is the market really changes over time. Right? So when we first started the company, we were mid-pandemic and the, the sort of team building part of our product was critical. It was urgent for people because everybody's teams were remote.
And then what happened is the market has shifted so that there are some companies out there for whom this is still critically important and they value it a lot, like Google. They're going on, you know, four years of using our product and really loving it. And there are other companies who are saying, "Yeah, you know, I don't really care about that. Like, if people... I don't... if they don't feel valued and they quit, I'm going to have a thousand applicants for every job." And so, even though I may personally disagree with that, I still had to evolve the product to meet the needs of companies who are in that mode. And I had to think about how to position our product not only for connection and value and trust building, but also for efficiency and productivity and larger spans of control. And I might have done that sooner. I think it's, it's working really well now that we've done it, but I'm kind of kicking myself for not doing it earlier on. So that's the first lesson.
And then the second one, which I'm sure a lot of founders talk about, is we definitely were in founder sales mode for the first, you know, many years. We've just this year brought on our first two enterprise sellers. I... we've had, we've had other people helping before, but not, you know, not in a complete like "I'm going to have a book of business." And you know, our, we have a very large lead pipeline now. So, I actually couldn't just do it myself. And I think had I rethought this or if I were to start over, I would probably do that sooner. I didn't want to do it because I wasn't sure where leads were going to come from, right? And then all of a sudden one day we had a lot of leads and I had nobody to service them.
Jake Aaron Villarreal: Yeah. Did... and have you seen a big impact with having those account managers?
Jennifer Dulski: I mean, they literally only started a month ago. So, so far I'm feeling, I'm feeling it personally like amazing. Yeah, it will be probably another few months before we start to see it in the company results.
Jake Aaron Villarreal: That's great. Well, I really love your story. If anyone wants to find Rising Team, Jen, where do they go?
Jennifer Dulski: So, we are at risingteam.com and we also have a site up at supermanager.ai, which is a new set of products we're building, which has a waitlist there if people want to sign up. And then you can find me at J Dulski. LinkedIn is probably the best spot.
Jake Aaron Villarreal: Well, thanks so much for coming on and sharing your story and for the listeners for listening. It means a lot to me you spent your time with us today. I'm your host Jake Aaron Villarreal signing off for now, but can't wait to catch up with you all on the next episode. Until then, Jen, the world, take care. If you like what we're doing, don't forget to subscribe, leave a review on Apple Podcast or wherever you listen, and follow us on YouTube where we go behind the scenes to learn what it takes to be a startup founder.
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