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Jennifer Dulski, Founder and CEO, Rising Team

From founding a non-profit, to working for some of the most influential companies on earth, and walking away to start again, Jennifer Dulski's career in the tech industry has been nothing short of extraordinary.

Jennifer talks to The Industry Leaders about how her work with Facebook shaped the way people around the world interact in online communities and shares the thought process behind leaving influential roles at tech giants like Yahoo!, Google, and Facebook to improve the lives of others.

For anyone that doesn't know anything about you, could you tell us a little bit about who you are and how you got to where you are right now?

My career in tech has lasted almost 25 years, but I actually started my career outside of tech by founding a nonprofit that was meant to help young, motivated, under-resourced students become the first in their families to go to university. I've always been really motivated by helping empower other people to be their best selves, and the reason I moved from that nonprofit into tech is because I wanted to do it on a larger scale. Getting into the internet was the way to scale up my impact to massive levels.

I have had executive roles at three big tech companies, Yahoo, Google, and Facebook, and I was president of for five years. I helped scale that company from about 10 million users to almost 200 million around the world — it's now double that.

I've also worked on several startups, one being The Dealmap; another is Rising Team, where we equip managers to build teams that are more connected, engaged and successful, which is timely given what's happening in the world of work with the pandemic. Now more than ever, remote and distributed work teams that are on the rise really need to get help in staying connected and being more effective.

Not only did you work for these impressive companies, but you walked away from them as well! For me, and for a lot of people, that seems like something that may have been difficult to do.

Can you talk me through the thought process behind that, and how you know when it's time to leave something seemingly fantastic or safe to start something on your own?

Yes, it's pretty interesting, actually. Sometimes, when I look back at my career, I realise how different it is from the traditional careers that I see people around me having for exactly the reason you talk about. Not only have I left big jobs that, arguably, had I stayed with would have become even bigger, but I've gone back and forth between very large companies and very small companies, which a lot of people don't do.

There are a few primary reasons why I've made those decisions. The first, as I said, is impact. Really, I've looked at opportunities as a way to think about how I can make a difference in the world, and that's, for example, why I left a very prominent job at Google to go to

The other thing for me that's been really important is learning and growth. I was at Yahoo for almost ten years. I had a great career there, starting as an individual brand manager on a single product, and ending as a group VP running one of their six big business units. But, I wanted to try my hand at starting something, at building something from scratch, at being a CEO and a founder. So, when I left, I took what was a pretty big risk at the time, but it was so meaningful to the rest of my career because what I learned there gave me so much knowledge and experience for the next things that I wanted to try.

I had a calm inner conversation with myself when I left to do that first startup because, as you know, most startups fail. I looked up the odds and found that, in fact, it was likelier that I would report having seen a UFO than it was that my company would succeed! So I knew that the likelihood of failure was pretty high, but I also thought, why not?

One of the pieces of advice that I've gotten in my life that's been so valuable is from a professor of mine at college who did research on regret. He said that, in the short term, people tend to regret what are called errors of commission — things they did that they wish they didn't do because they feel silly or embarrassed about them, or they failed. But, in the long term, in our lives, we tend to regret errors of omission — wishing that we’d tried something that we never did. So I took the leap to see what would happen, and I think it's been a great run.

About my decisions to leave, though, I'm not sure everyone thought it was brave; I think, maybe, they thought it was stupid. Even in my career at Yahoo, when I ran marketing for two-thirds of the company, I decided that I really wanted to be a general manager, so I applied for a job doing that instead. And, while I was offered the job, they said that I would have to take a demotion to take it because it's at a lower level than being, essentially, SVP of marketing.

A lot of people thought that taking that demotion was a really bad decision, but, for me, it was a decision that put the whole rest of my career on a different track that it couldn't have moved to otherwise.

So, sometimes these decisions look silly on the outside, but they actually make a lot of sense.

When delving a little bit further into your background, I noticed that you were on a rowing team at university — a fairly successful one as well. Do you still do that? If you don't, what's your competitive outlet outside of work?

Yes, it's true, I was a coxswain on the rowing team in both high school and college. I actually credit that experience for most of the leadership skills that I have because it's actually just such a great experience in learning how to get a team of people to work together and to push themselves harder than they think they can go. You have to give feedback to people in real-time in front of everyone else, and you have to understand each unique individual and how to motivate them. I also had to learn how to earn their respect because, though I was in the boat, I wasn't rowing. All of these lessons have come with me throughout my career.

I don't cox crew anymore, but the one thing that I do love to do is take part in a workout program we have here called Orangetheory. It's basically a boot camp style workout where you wear a heart rate monitor that shows you different colour zones for levels that your heart rate can reach. And you get rewarded with points depending on this, so it's a sort of competition with yourself. You workout in a group so you can see how well you're doing versus other people, but I mainly do it to compete with myself. That's one of my favourite activities to do.

You authored a book called Purposeful. What is it that gets you up in the morning? What's your purpose for doing what you do?

My purpose has always been to work out how I empower other people to be their best selves. As I said, it started in my life in education, but I believe that there are two major levers where you can have an impact on people's lifetime trajectories: one is school, and the other is work. So I've been building products to empower other people, whether it be through information at Yahoo and Google, through community at Facebook, through amplifying people's voices at, or now, at Rising Team, where we’re all about helping people in the workforce feel deeply understood, supported and able to reach their goals.

The purpose piece is really important because the way that I think about life as an entrepreneur and as a leader and, really, as a human being is kind of like climbing a mountain. Some days are super sunny, and I’ve brought a picnic lunch, and I can see the top, and other days are just really cloudy, and there's a huge storm coming, and it feels really daunting. For me, purpose is the thing at the top of the mountain that, once I’ve got there, makes me want to keep going whether it's sunny or cloudy. I've also found that it helps a lot to be climbing with other people that you respect and trust and want to keep climbing with. Purpose can lift us all up together, even when times are really difficult.

The work you did at Facebook has really shaped the way all of us consider communities now. Given that, what advice would you give to someone who's either starting from scratch or is struggling to build a community?

When I first started thinking about community, which was way before I worked at Facebook, I learned some really important lessons from Catarina Fake, one of the cofounders of Flickr. She built this thriving community, which, although it's known for sharing photos, is really more of a community site.

Catarina said that building a community is like hosting a party in that you have to actually nurture people: when they come, you have to introduce them to other people; you have to take their coat and start conversations; you have to make it feel like a welcoming place, and you also have to take care of conflict when it arises. If a fight breaks out in your party you want to do something about it right away. If you really nurture people and embrace your first followers, your community can really thrive.

Building a community is like hosting a party in that you have to actually nurture people

People have two questions when they join a community. The first is, are they like me? And the second is, will they like me? And so what you're really trying to do when the first people join is to help them answer those two questions. You're making the introductions, you're getting the conversation going, and you're doing what I call embracing your followers. It's the same as starting a movement. If the people who join in those early days feel active and engaged they will then welcome others to create a virtuous cycle.

So, for instance, at Facebook, we found that communities that could get 50 people joined up in their first week would be much more likely to be actively engaged because it meant that something was working early on. Those first set of people would then help make the community vibrant going forward.

The other thing that I think is important, which we've done at Rising Team, is making your team feel like a community. So, in addition to welcoming new team members and embracing people, one other major driver of community is tradition. It's the reason why physical communities have secret handshakes and so forth.

We don't have a secret handshake at Rising Team, but we do have things like themed team meetings, and acronyms, and emojis that are customised to us that we use in Slack. And, as part of the product we're building, we're giving those tools to other teams so that they can make their own teams feel more like a community.

As well as your work with Rising Team I know you’re also lecturing in management at the Stanford School of Business. What sort of differences do you see in the people that are coming through as managers and leaders now compared to those you might have worked for in the past?

It's fascinating because everything we know about the world of work has changed, essentially, in just the past two years. Work has been evolving for decades, but in the past two years, everything has turned upside down. We went from a world where almost everybody worked in-person to a four to five-times increase in remote and distributed work, where almost every company has at least some portion of their workforce remote. Also, the inappropriate things that might have been happening in the workplace are now being called out and placed front and centre.

We have also moved to a world where employees have dramatically higher expectations of their employers. As you know, we're in the middle of the 'Great Resignation' — nearly half of all people are planning to leave their jobs in the next three to six months. So it's incumbent for leaders of companies and managers of teams to understand what drives and motivates each of their employees and to help provide those things for them.

There's a recent McKinsey study that I think captures this so well. Basically, they made one chart that shows what employees want and one that shows what employers think employees want, and they're quite different. The things that employees really want at work are to feel valued by their organisation and their manager. They want to feel a sense of belonging, they want trust and care with their teammates, and they want to feel like they have opportunities for growth. These are some of the reasons why what we're building at Rising Team will end up being so much more important than we might have thought even a few years ago.

This is the kind of thing that I teach at Stanford now, too. We teach all sorts of traditional frameworks for making good decisions and hiring and coaching people, but now we also think about how to lead in today's environment. One of the things we do is practice and roleplay a lot of these situations with people to help them understand how to actually do that.

Another tool that I talk about at Stanford is a basic concept that I call the two Cs: “clarity” and “compassion”. I think sometimes people get confused about these things; they can be so focused on clarity that they forget about compassion — they forget that they have to actually take time to empathise about people's lives outside of work and take into account all that's happening in the world today.

And then sometimes people get so focused on compassion that they forget to be clear about their expectations. So people end up getting stuck and underperform because they weren't really told what their goals should be. So I really try to get managers to focus on the combination of those two things in equal parts. Some people prefer slightly more clarity and some people prefer slightly more compassion, but everybody needs both.

So that is one tool people can use to start thinking about how they can do better in understanding, supporting and coaching their team.

To add a third ‘C’, I want to talk about challenges. What's something particularly challenging that you’ve overcome on the journey to where you are today, either personally or professionally?

There’s been an immeasurable number of challenges on the path. The thing about careers is that they are not a straight line. There are so many bumps along the way, both professionally and personally. On the professional side, I've had so many challenges, but one of the largest ones was when we went through a change of our business model at

When I first arrived there, we had an advertising-based business model, and I was responsible for helping that grow. One of the things we did was to hire a lot more salespeople and client services. The business grew successfully for a number of years, but it then became clear that we wouldn't be able to grow it further when we began competing with Facebook and Google, so we had to shift the business model away from advertising and towards subscriptions.

Part of all of that meant that we had to let go of the entire sales team and client services team that we had hired, and that is one of the bigger professional challenges I have faced because I knew that it was going to negatively impact so many people and their lives, and I felt personally responsible for that. I did everything I could to be generous in that process and to try to help people find jobs afterwards and so forth, but there's no making something like that easy.

The other kinds of challenges I've come across are the personal ones. Anyone who reads my book, Purposeful, will read about several of these. I've had a few incidents, for example, with my daughters, where they each separately got into quite serious accidents and ended up in the hospital. It's moments like those that really put everything else into perspective. Suddenly you realise that any challenge you're facing at work is just so small in comparison to the things that we really value in our everyday lives.

Either as a parent or as a mentor, would you recommend the same path that you’ve taken in business to your daughters? Would you say, go and start things, leave big companies, set things up? Or would you say, study, get the job and stay in a stable career?

I try not to give direct advice to my own children like that because I often find that it is either not effective or welcome. Honestly, what I want them to do is just find things that they love. The Japanese concept of Ikigai combines the things you like and love, and the things you are good at and can be paid for, with the things that the world needs. If you can find the middle of that, you are in the absolute sweet spot.

I love the career I have had, and, at the same time, I feel like Rising Team may be the first thing that puts me right in the middle of that. If you asked me what my favourite days at work were, I would always say it was a day where we were doing team building and getting everybody aligned and helping people feel connected. And now I get to do that work every day.

So, I try to encourage people to find the things that really do light them up and to find ways to spend more time doing those things because they'll be happier and more successful if they do that.

Is there anything that you find yourself listening to a lot, in terms of podcasts or audiobooks - is there anything that you kind of can't live without?

I do read a lot, and I listen. The things I read tend to be more news and newsletters, whereas the things I listen to tend to be more fun. My favourite podcast is Wait Wait... Don't Tell Me! which is a news trivia game. But I read lots and lots of newsletters. I read Axios; I read Stratechery; I read Lenny Rachitsky’s community letter. There's lots of really great content out there about our industry, about the things that we're trying to build, about examples of what other people are doing, that I find really motivating and inspiring.

Then, there are a couple of books that I have kept close over the years, books that I always recommend to people. One is a book called Gung Ho!, which is a Native American folk tale about lessons we can learn as leaders from animals. It sounds so unlikely, but it's really, really interesting. Basically, there are three sections that each talk about something that's really important in leadership. For instance, it uses the example of the spirit of the squirrel to talk about purpose. Squirrels spend all this time collecting acorns because they know its purpose is to get them through the winter; they have this very clear purpose that drives their motivation. That's a really great book.

The other one that I love is The Alliance, which is by Reid Hoffman, and it talks about the fact that we can't assume that people on our teams or at our companies will be forever loyal to our companies anymore — it’s so relevant to the Great Resignation. It says that if we want something from our people, we have to be able to give them something in return. And it talks about the concept of seeing people's time with us as tours of duty, where we ask them to do something specific and help them gain something out of it, and then have that be complete before thinking about the next tour of duty. I think it's a really interesting concept.

You've mentioned that a couple of times, and it's something that I see all the time on LinkedIn — ‘The Great Resignation’. Is this something that you guys are dealing with in Rising Team?

Our team is so small still and so relatively new that we haven't had anybody leave yet. But I wouldn't be so naive as to think it couldn't happen to us because it can happen to anyone. If the great resignation involves nearly half of all people, it must be nearly half of our people too. So this is why we spend so much time really trying to understand what each person cares about and how we can help them feel fulfilled, happy and engaged at work.

What’s next for you and Rising Team?

First, our goal is to try to have more teams benefit from the product. So we're really thinking about how we can make it great for any type of team that's using it. We have everyone from very large companies to nonprofits.

There's a really wide range of people, so we want to make sure that it works well for the variety of use cases that people need. Right now, people are using the product in their individual teams that consist of a leader plus up to ten people, but we also want to think about how they could use it with 50 or 100 people. Could we do breakout groups? Could we do roll-up data that gives people that broader team or company view?

The other angle we’re thinking about is what needs to be adapted as we go into different industries. So, for instance, the folks who are using it in Australia are saying that they'd really like school leaders to be able to use it, too. For that, would it work exactly as we've built it, or would it need to be adapted? And, if so, how do we adapt the tools to suit the unique needs of that category? So those are some of the things we're thinking about. Right now, though, we're just so excited to see people getting value from it, and that feels really meaningful.

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