The Female Founder Show
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The Female Founder Show
From Teacher to Tech Trailblazer: Jennifer Dulski on Leadership, Teamwork, and Mentorship
Discover how Jennifer Dulski, CEO and founder of Rising Team, transformed her career from high school teacher and nonprofit founder to a trailblazer in the tech industry. Jennifer's journey through leadership roles at Yahoo, Google, and Facebook provided a unique foundation for her to create a company focused on enhancing teamwork dynamics. In this episode, you'll learn how her diverse background helped shape Rising Team and why taking small, actionable steps can be the key to launching your own venture.
The importance of mentorship and balancing personal life with professional responsibilities takes center stage in this conversation. Jennifer shares her wisdom on the concept of a "work-life mashup," showing us how integrating family with our work lives, and releasing guilt, can lead to enhanced performance in both arenas. Drawing inspiration from her book "Purposeful," we explore how everyday individuals can utilize entrepreneurial strategies to drive significant change in their lives and communities.
Building trust and connection within teams is more critical than ever in today’s evolving workplace. Jennifer explains how Rising Team equips managers with the tools to foster psychological safety, appreciation, and effective feedback, ultimately improving team dynamics and productivity. We also explore Jennifer's global vision for Rising Team's expansion, touching on its current impact across various sectors and her ongoing dedication to teaching, mentoring, and supporting other female founders. This episode is packed with practical strategies and inspiring stories that will leave you motivated to lead with authenticity and vision.
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This is the Female Founder Show with host and entrepreneur Bridget Fitzpatrick, exclusively on ASBN.
Speaker 2:Hello everyone and welcome to the Female Founder Show. I'm Bridget Fitzpatrick and I'm so excited to talk with today's guest, jennifer Dulski, ceo and founder of Rising Team. Jennifer, known for her innovative leadership, has established a stellar career where she has worked with Yahoo, google and Facebook before starting her company, rising Team. At Rising Team, jennifer is reshaping teamwork dynamics with cutting-edge strategies, and her impact has been inspiring women worldwide to break barriers and pursue their dreams, and that's what we're all about here at the Female Founders Show. So with that, jennifer, thank you so much for joining us. Thanks so much for having me. Great to be here Now. There's so much more to your story than what I just mentioned, so can you share with us a little bit about your background?
Speaker 3:Yeah, I have a pretty atypical background into getting into a career in tech, which is that I started my career as a high school teacher, and I started a nonprofit to help motivated and under-resourced kids become first-generation college graduates.
Speaker 3:So, in a way, I was a founder from the beginning, but the fact that I worked in education and was a teacher is pretty unusual for folks who have careers in technology, and I think it was actually really helpful, because it gave me a deep understanding of how to create a vision that you could get people excited around, and how to raise money for something and get it off the ground.
Speaker 3:And the reason I moved from nonprofit into tech is because I was looking for ways to create impact at larger scale, and I knew that in the nonprofit world, I could raise twice the money and serve just about twice the people, and it felt like, if I did this through tech, there would be a way to scale it much more exponentially, which was true. The surprising fact, I will say, though, is that you know that nonprofit that I started is now going to hit its 30th anniversary this summer, so sometimes you can create things and they do scale dramatically. It just takes a lot of time, and so, anyway, I then spent the next 20 plus years working in tech. I've had leadership roles, as you mentioned that. You know several of the big tech companies, and then I've done three startups. I'm on my third one.
Speaker 2:Well, congratulations, very, very accomplished. So you're now running Rising Team. Talk to us about the motivation for starting Rising Team.
Speaker 3:So this happens with a lot of founders. I'm essentially building the product I wish I had had as a leader of teams my whole career. So I knew in all these roles I had leading very large teams that the companies I worked in were more successful when the teams were successful, when individual people felt motivated and inspired to do their work and connected to each other. And I didn't feel like I had the tools I needed to do that at scale. So you know, I was lucky to have executive coaches and be sent to really amazing trainings, but it always felt to me like I was being taught to fish and then I would have to go back to the lake with like the book about how to fish instead of the fishing pole and the bait. And so what we build at Rising Team is that fishing pole so that every manager on all kinds of teams can build deep connection and improve performance on their team.
Speaker 2:I love that. I love that. So you saw the need and you created it.
Speaker 3:Yes, and it's kind of, in some ways it feels like the company I've been meant to build my whole career. It's like the culmination of everything I've done, because the teaching and the scaling teams and actually even early in my life I was a coxswain on the rowing team. I don't know if everyone knows what that is, but I learned a lot of lessons about leadership and about team building through various points in my life and all of that is coming together into building Rising Team.
Speaker 2:So, as a successful female founder yourself, what advice would you give those entrepreneurs that are just starting out?
Speaker 3:So my number one piece of advice is just get started. The hardest part about being an entrepreneur is just overcoming the friction to do something. It can feel really scary and in fact, when I started my first company, I looked up the odds of success and it turns out I was more likely to have reported seeing a UFO than I was for my company to succeed, because one in eight US adults has reported seeing a UFO and only one in nine or 10 venture-backed companies succeed. But I thought to myself I will always regret this if I don't try. And so the key is you know you don't have to raise millions of dollars day one. You wanna just start with a small step. And you know we'll talk about it a bit later.
Speaker 3:But I wrote a book called Purposeful, about how all of us have the power to be movement starters and entrepreneurs, and everything big that people start all begins with a small step. So for Rising Team, as an example, the first thing that I did was just write an outline. I didn't, you know, go try to do something big. I just got it down on paper. What's the problem I'm trying to solve? Who are the customers? What are their needs? How might I solve this for them. And then I started talking to a few people about it, and it's one small step and a second small step, and that's how things blossom.
Speaker 2:That's great advice, and not only you know mentioning just get started, but also what you did when you just started, because a lot of times they just just start it, but okay, what does that mean? So thanks for sharing that. That's great advice.
Speaker 3:Yeah, absolutely, and they can. The just get started can be all kinds of different things, you know. Sometimes people write an email to their friends, sometimes they gather people together, Sometimes they do a build a little mini prototype. It can be any version of it, it's just. You know, like they say in yoga, get on the mat. That is the hardest part of yoga.
Speaker 2:Yeah, exactly Now. We all experience setbacks and challenges as founders. How do you navigate those challenges and maintain motivation and positivity?
Speaker 3:Yeah, this is, as it turns out, the number one skill of being an entrepreneur is just pure resilience, and you know I liken it to climbing a mountain. I say, you know, being an entrepreneur or a founder is like climbing a mountain. Some days it's super sunny and I brought a picnic lunch and I can see the top and it looks amazing. And other days it is a giant storm and I feel so defeated and I can't even see the top. And sometimes literally those things happen on the same day. So I remind myself of a few things.
Speaker 3:One is do I care about what I'm climbing? For If you're passionate enough about it, it makes you want to keep climbing, regardless of whether the day is dark and stormy. Two is who am I climbing with? So if you bring people along on the journey with you that you love to work with and climb that mountain with, even on the dark days, you can support each other. And the third is just one step forward. It's the same as starting with a small step. The idea is, days will go back and forth and we know that. So I remind myself, on the stormy days it will get sunny again, and in fact sometimes I have days, or even weeks or months where multiple bad things will happen in a row and I just keep saying to myself something sunny is going to happen, and invariably it does. And then the key also is to not stop and slow down too much when the days are sunny, because you want to keep moving forward Even when things feel great. That's how you ultimately win in the end.
Speaker 2:I love all of those steps, and you mentioned support and who you're climbing with. Have you had any mentors along your journey and, if so, how have they influenced you?
Speaker 3:So many mentors.
Speaker 3:So I have a saying that I use, which is every person is a teacher and every experience is a lesson, and I developed this, actually when I first started writing on LinkedIn.
Speaker 3:So in 2013, linkedin asked me to become one of the early LinkedIn influencers, and to do that, it meant I had to write regularly on LinkedIn, and at that time, I wasn't writing a lot and I just thought, gosh, what do I have to write about that I can just talk about all the time?
Speaker 3:And so what I did was I went back through my life and I thought about all the people in my life and all the experiences, and I started writing posts called Five Lessons I Learned From, and it turns out I could come up with five lessons from just about anyone. I wrote one about each of my parents, I wrote about many former bosses, I wrote about experiences like teaching high school, or I went abroad into the Amazon rainforest, and each of these things taught me many, many lessons. And so when I think about mentors, my view is just they're all around us if we keep our eyes open to learning from them, and I've learned so many things from my various mentors, like how to be a better listener, how to be resilient in tough moments, how to show up with confidence when you need to all sorts of different things from different people.
Speaker 2:That's great and it's a constant. So always learning, always learning. So I'm sure you get this question a lot. I do. Balancing work and your professional life, your personal life, can be tough. So how do you prioritize self-care and maintain a healthy work-life balance?
Speaker 3:self-care and maintain a healthy work-life balance. Yeah, so I am also a mom and I do. I get you know. I teach. I teach two classes at the business school at Stanford and I get this question all the time from students mainly female students, but also male students sometimes, you know, asking about how do you do it, how do you be an entrepreneur and be a parent, and I use a term I call the work-life mashup.
Speaker 3:So I don't believe in work-life balance. I actually think it's like not really possible. The idea of balance suggests that some things are equal all the time and there's just no way that these things are equal. So I have tried in my life to merge them together. So a mashup is like layers of music on top of each other or applications, and that's kind of what I've done. You know, I was running my first company when my kids were small and so I did things like put our office across the parking lot from the place where they took dance lessons every day so that they could, you know, run over and I could do their bun in the middle of the day before they went to dance, and then they'd do their homework at our office afterwards.
Speaker 3:And you know, as a founder, you have the flexibility to do things like that, which you don't always have if you work inside large companies.
Speaker 3:And I've done both and I've found a way to make it work in both. My number one. So I guess I have two learnings here. One is it's okay to merge them together and people are actually better colleagues and better teammates when they understand each other's lives outside of work. And so I have not shied away from, you know, bringing my kids on work trips with me and things like that.
Speaker 3:The second is guilt doesn't make me better at either work or home, and so early on I felt guilty a lot of the time. I thought, oh, I went back to work too soon after I had my child. I you know they're not, they're not going to be as close to me because I'm not spending as much time at home realized over time that feeling guilty about it didn't make me a better mom and didn't make me, you know, feeling guilty about work didn't make me better at work. And so I learned to most of the time, just put the guilt aside and say I'm just going to do my best. That's all I can do. I can do my best.
Speaker 3:And there were definitely moments that were challenging. I tell a story sometimes about how, when my older daughter was like three or four, she was at the playground and she was in one of those little playhouses and I went in and I said can I play with you? And she said I'm in a meeting. Oh my God, this is how she already sees me. But you know, it turned out okay. My kids are in their twenties, they're. They have great lives. We have a good relationship and I did my best. That's all I can do. That's great.
Speaker 2:And they saw you doing your best and I'm sure that was very helpful. Yeah, that's a cute story and thanks for sharing that, because I think that a lot of people watching this show are moms and do feel that guilt and it's probably hard to put aside. But, like you said, it's not. It's not doing you any good, it's not doing your family any good, it's not doing your business any good. So, if you can put it aside, yeah, let's talk about your book Purposeful, bestselling book Purposeful. Are you a manager or a movement starter? Talk to us about that and some of the takeaways that you'd like for our audience to know.
Speaker 3:So I wrote that book. While I started writing it, when I was president at Changeorg. So my job was to scale and amplify people's voices all over the world around the campaigns that they cared about. And what I saw happening, which was amazing, is that regular everyday people you know, teenagers and grandparents and moms and veterans were starting these campaigns to create real change in the world, either in their local community or nationally, or sometimes globally, and they were all kind of following the same formula. And actually that formula looked very similar to what I had seen in Silicon Valley of these people who start big, successful companies. And so I thought if I could give people the formula, maybe more people could do this successfully and start these world changing movements and campaigns or start big, successful companies. And so that's what the book is about.
Speaker 3:There are seven key steps to doing it, but I have since shortened it into what I call the big three C's, and those C's are courage, community and commitment. And we've already talked actually about two of the three C's, because the first is courage. It's taking that small step just getting started. I sometimes compare this to being like being the first one to start a standing ovation when the show is just pretty good, like you're not positive that other people will stand up, but you try it anyway. It's that kind of feeling, that's the courage. And then, and by the way, almost never do people start a standing ovation and no one joins them even though it feels uncomfortable.
Speaker 3:That's a good point, and so, yeah, and so then the second C is community, because you can't really create anything of meaning and value if you don't have people joining you along that journey, and a lot of it is. How do you tell the story and craft a vision that inspires people? And then how do you welcome people into that tent and give them roles and responsibilities so that they can carry on and build it alongside you? And even without you, like, if I think about that nonprofit I started, it's been running 30 years. I only stayed the first four. It didn't actually need me for the next 26 years.
Speaker 3:And then the third one is commitment, which we talked about the mountain, like the number one reason that businesses and movements fail is because people fall down and don't get back up again. And the truth is we're just going to get knocked down over and over and the real path to winning is just okay, dust myself off and and get up again. So that's what it takes. And then there are some other tips in there, like about understanding the people you're trying to persuade and not getting caught up in what I call the haterade and all of that. But the key to being successful are three Cs.
Speaker 2:I love it. I love it. Thank you for sharing that. Now I would love to talk to you about how you're helping managers and team leaders at Rising Team. Your software shares kits to help leaders build connections, and so much more. Can you talk to us a little bit more about this?
Speaker 3:Yeah. So you know, we're in a workplace that is just massively different and pretty challenged right now. So if you think about the way work has evolved over the past three to four years since the pandemic, we're now in a spot where 75% of all teleworkable jobs are hybrid, so people don't work in physical offices as much anymore, meaning they don't see each other that often. Many companies are struggling with what we call RTO mandates return to office. So am I forcing people to be back in the office, am I not? How many days a of wanting to feel valued and a sense of belonging at work, and now we have AI excuse me coming in on top and pressuring everybody to think if I don't learn this, I'm going to lose my job. So this is an overwhelming workplace we're in right now and um and it all lands on managers.
Speaker 3:The poor managers are the ones who have to help their teams navigate this, and we just don't equip them.
Speaker 3:The current ways that we equip managers are insufficient, because we either train them by themselves with video or kind of on-demand content and give them nothing to bring back to their teams, or sometimes we give them coaches and facilitators who are really helpful but very expensive and hard to scale throughout an organization, and so what we do at Rising Team is that we give managers these kits, as you mentioned, which help them guide their own team without a facilitator, through deeply connecting team workshops on key leadership drivers of high-performing teams, so things like psychological safety and appreciation and giving feedback, and then also pure connection sessions that are just about how I get to know you better as a human being, and we suggest that teams do these a couple times a quarter. So not a lot of time, but with that limited time, just the idea of setting time aside to get to understand each other better. We've shown 100% of our customers move, their employee engagement scores, their employee net promoter score, manager effectiveness. All of this goes up just by giving managers the tools to better understand their teams.
Speaker 2:That's awesome, and you know, business owners are nothing without the hard work of their teams, and so, in your experience, what's the number one mistake that leaders are making when it comes to their teams?
Speaker 3:Yeah, so the number one mistake people are making is thinking they don't have time to build connection. So I and this is the number one mistake people are making is thinking they don't have time to build connection. So I and this is the number one pushback we get to people using rising teams I don't have time, We've got too, we're too busy, we have too many goals, et cetera. And the thing I always point out are you a Top Gun fan? Did you watch the movie Maverick?
Speaker 2:Yes, I watched, I did yes, it was very good.
Speaker 3:So I am a big Top Gun fan. I've seen the first one too many times that I want to get, and the second one a few times as well. And there's a great scene in Maverick, the new Top Gun, where he takes the team to the beach to play beach football. And theiral comes to the beach and he says what are we doing? We have this important mission. Why are we here playing games? And Tom Cruise turns to him and he says you said to create a team, sir. There's your team and that is flag football. And my view is probably we can do a little bit better than flag football because we can build deeper authentic connections. But to say I don't have a few hours a quarter to spend time making my team feel understood and valued is why our teams don't feel understood and valued. And when they don't feel that way, they quit, or they quiet quit or they're just unproductive and unhappy. So that's the number one mistake is I don't have time for that.
Speaker 2:Okay, and you talk about community a lot, and part of that is trust, and it's a huge part of leadership. What advice can you share that helps leaders build trust with their teams?
Speaker 3:Yeah. So trust really comes from understanding each other as humans. So it's funny before I built Rising Team when people used to come to me and say, oh, I'm having a conflict or we have this disagreement on the team, my advice was always go have a beer or a cup of tea Before you get into like, oh, we're fighting about this work thing. Just understand each other first, because usually that explains why the things are happening. People don't act a certain way out of nowhere that you know. There's things going on in our lives all the time. And you know I one of my favorite books is called Everybody's Got Something by Robin Roberts. I don't know if you've read it. She's incredible. Good morning America. And yeah, and she's been through a really difficult multiple personal health battles and she says everybody's got something. And she's been through a really difficult multiple personal health battles and she says everybody's got something. And it's just so true on any given day.
Speaker 3:So I sometimes give a talk about this topic and I asked this question how many of you have received a phone call with serious medical news at work about yourself or someone close to you? And like, 80% of the audience will stand up to that question because we all have. We've all gotten that call about a parent or a kid or ourselves while we're in the middle of a work day and when you ask that question and people stand up and they look at each other, it's this huge aha moment, like I am not alone. And that's what builds trust is understanding. We are not alone and that comes from understanding what's going on in each other's lives outside of work.
Speaker 3:It doesn't mean you have to know every personal detail about people's. You know addictions and divorces and all of that, although if they're willing to share, it might help you work better together. Right, you understand? Right, Exactly. So that's my view is trust comes from understanding. It comes from listening. We are building tools to make it easier for people to do that, because sometimes it's hard to get into those conversations. So you know, we have also short mini kits that are 10 minutes long that ask questions like how do you like to be supported on a bad day?
Speaker 2:Okay, good, I'm glad you mentioned that because I was wondering how do you pull it out of the team members that just might be more introverted or quiet, or maybe they don't feel like sharing. But I guess you're about to go back.
Speaker 3:Well, the first thing is people. We have a set of ground rules we start with and we tell them to only share what is comfortable to them. So we never want to push anyone to where they're feeling uncomfortable. The second thing is that the leaders who are facilitating so the managers or the team lead. We give them a little bit of training before they facilitate these sessions. And oftentimes we encourage them to share first, because usually if someone gives an example of more open sharing, then it encourages other people to be a little bit more open as well. And we also always give people options Like you can share either a personal story or a work story. You can share someone really close to you or a little farther out. So we try to give people choices so that they never have to get uncomfortable. And then you'd be surprised how basic, simple questions like how do you like to be supported on a bad day, or what makes you feel really appreciated at work, can really unlock, you know, understanding of people that you didn't have before.
Speaker 2:That's. That's awesome, so I'm going to change gears here for a second. You have been in the tech industry for your entire life, which is a very male-dominated industry and there's only about 15% of women tech CEOs, so talk to us a little bit about that and how you navigated that.
Speaker 3:Yeah, it's true, I have been a woman in tech for a really long time and when there weren't very many women, and especially during various points in my career, I also ran very male-oriented business like Yahoo Autos, as an example, where I was like the only woman at the JD Power Conference. I'm going to one next week. So now it's different. I will say there's a lot more women in tech than there used to be. And so now it's different. I will say there's a lot more women in tech than there used to be, and I always say that we'll know we are done with this battle when we no longer have women in tech panels at conferences, because we won't need one anymore. Women will be on all the panels. But we're not quite there yet. And it's even harder.
Speaker 3:On the entrepreneurship side, I will say when I my first startup, we ended up selling it to Google and I went to my first founders at Google event and I was the only woman and I asked them is it possible that no other female founders have ever sold the company to Google? And they looked it up and they said, nope, you're the first one sold the company to Google. And they looked it up and they said nope, you're the first one, and that was 2011. Now there have been many more. So you know things are getting better over time, and I think what helps a lot is having a strong network. So I posted recently for International Women's Day about some of the women I met early in my career who are still deep, close friends to this day, and finding other networks of founders in general, and also female founders, just helps get you through that journey.
Speaker 2:Yes, now you've accomplished so much in your career and you're so inspiring. So what is next for Jennifer Dulski?
Speaker 3:So my first goal is to get Rising Team to every team on earth. That's my vision. I'm not really kidding Like. We already have it being used on six continents, and we have it in big tech companies, and we have it in government offices and schools, and the amazing thing is that the same content works in all those places, because high performing teams are driven by the same thing, which is feeling safe and valued and doing their best work and so forth. And then, after that, you know, I started teaching again in 2020 and it's a real passion of mine. So, instead of high school, I teach business school. But as I think about going forward, in addition to Rising Team, for me it'll be teaching and boards and helping other founders. So that's why I'm excited to do things like this.
Speaker 2:I love it. Thank you so much. Thanks for sharing all your advice with our audience. I'm sure it's going to help so many people. Thank you so much for joining us on the Female Founder Show. Your story and advice are going to inspire and help so many, like I said, so we really appreciate it.
Speaker 3:Thanks so much for having me.
Speaker 1:This is the Female Founder Show with host and entrepreneur Bridget Fitzpatrick, exclusively on ASBN. If you're a female founder and would like to help other female founders with your inspiring story, we would love to hear from you.