Lift up one other woman every single day

“If I could build anything, what would I actually build?”

This is a question Kelley Steven-Waiss asked herself as the CHRO of Here Technologies when she couldn’t find a tool that helped properly manage talent at her organization.

So instead of settling for a tool that wasn’t quite right, she built her own software solution in-house.

Her homegrown solution was so impactful that she ended up spinning out of Here Technologies and launching her own company, Hitch Works, to commercialize the software so she could help talent leaders everywhere better manage their talent.

Hitch later got acquired by ServiceNow, where Kelley works today as the Chief Transformation Officer.

Kelley’s founding story is inspiring: She experienced a problem, created a solution and then scaled the business because there was a serious gap in the market that she helped close.

In this episode, Kelley shares how her intrapreneurship to “entrepreneurship experience inspired her to write her book: Valley Girls: Lessons from Female Founders in Silicon Valley and Beyond.

We also talk about how motherhood played a role in her success, as her family gave her perspective and motivation throughout her career.

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Allison: Kelly, thank you so much for joining me today on The False Tradeoff.

Kelley: It's so great to be here, Allison. Thank you.

‍Allison: We are here primarily to talk about your book, Valley Girls: Lessons from Female Founders in the Silicon Valley and Beyond. I'm really excited to get into the lesson piece of this, but you also talk a lot in your book about your personal story. And so I thought, let's start there because I think it actually sets a really good context for this conversation. And then we can transition into some of the lessons you learned when you went out into the world and talked to many other female founders.

So starting with your story, you have a very long and impressive career, but I wanna start at the moment in time when you started to make your, I imagine your biggest pivot, which is you were at Here Technologies. Tell me about how Hitch was originally created and sort of incubated and what that process was like from the idea and sort of the MVP into ultimately, spinning that out into your own company.

Kelley: It really started because I was sitting in the CHRO seat. And so I was experiencing not only having been an employee, not feeling seen, valued and heard, but as a CHRO, seeing so many people walk out the door that had skills and capabilities that we often needed two months later, or they were not getting moved around the company appropriately. We would always just try to solve it with putting a rec out. 

And so I  couldn't find the software that I was looking for. So I just said, you know what? If I could build anything, I went into a conference room and said, if I could map out what I would build, kind of like zero-based budgeting, zero-based planning, what would I actually build? And I took that idea to the CEO and said, I know we're trying to transform this company. I know we're trying to build talent in a different way.

Why don't you let me build this as a tool here and we'll use it and if it's successful, right? It will make a difference in the company. So it wasn't intentionally to commercialize it, but at the start, we started to implement this product in the organization. We were having such success that it got spoken about externally. 

And I went back to him and said, I think we can commercialize this. And so we did. I started selling into my own network and not only was it having an impact on our organization, but all of these other companies were seeing the benefits. And so, you know, I had all the typical things that you would on the outside, you know, swimming upstream against leaders who are like, what do you have a side hustle for? And, you know, the change management around something brand new and disruptive. 

But it was, you know, it was such an exciting time in my life professionally. I was so personally vested in the mission of what this software could do for organizations and for the people inside those companies that, you know, I had a, I was waking up every day with a mission and a purpose and that really, you know, it really took off and it was, I was really the pioneer of what we call internal talent marketplace or ITM, which Gartner later named the category. And it was just, yeah, very fulfilling for me professionally.

Allison: And then tell more about how you spun it out of here, because I thought that was a really interesting piece of the book as well. Yeah.

Kelley: Yeah. Very fascinating. So the board came to me in April, the first week of April of 2020. And remember, we were all in lockdown due to COVID and said, hey, this is non-core, you know, great job, did a great job with it, but it's non-core to the company and we're cutting off funding to all things non-core. We're going to tighten our belt and you need to spin this out. 

Well, I had never pitched venture capital or spun out anything. So I got corp dev involved to start working on a carve out while I started to pitch investors. Now pitching investors when no one's in the office and no one's meeting, you just outright get rejected like, Hey, we're not doing any investments or deploying capital right now. You know, they were trying to figure out what to do.

But there were a few that met me on the Stanford campus and walked with me, social distancing and let me pitch my software. And so it was kind of to find a creative solution and do your best influence. And I ended up with one term sheet, not three like you'd like, but that one term sheet took me and 25 people out. We successfully spun it out in less than 60 days. So on July 1st of 2020, we were a venture backed company. 

However, I will say when you wake up the next day and you went from being a C-suite executive in a large enterprise to founder and CEO on your own with whatever millions you have to last, that pressure is like no other pressure. And there certainly was the high bar of we're all in the great experiment called COVID-19. So it was a challenge.

Allison: That's wild. At what point, or maybe there wasn't one point, did you decide I'm doing this? Because I have to imagine you had other opportunities to stay there or do something else, but how did you make that decision? You'd never been a founder before. We're in the midst of a global, or beginning of a global pandemic. What made you feel really great about that decision, and how did you make that decision?

‍Kelley: Well, my friend said I was in a midlife crisis because I had just recently turned 50. I had kids going to college every two years, right? So by all, add up all of the variables, that was not a time to go and do something disruptive, not only professionally, but to your family, right? Because you're taking a lot of risk. But for me, it was…no questions, right? Like you, there is a reason why you got that term sheet. This is going to make a huge difference in the world.

Allison: Right. You mentioned risk a few times. And so I want to double click on that a little bit. I loved the portion of your book when you talked about bootstrapping versus raising money from investors and what those tradeoffs are. And you specifically talked about your family when you were debating whether you bootstrap or not, and feeling like you couldn't put so much on your family.

I deeply resonate with that feeling. I actually bootstrapped parentally for two years, which at the time, was the right decision. And I got to a point where I thought I can't keep risking so much for my family. And so when I read that part about your story, I thought, Oh, I'm just, I'm dying to learn more about your thought process and also to dig a little bit more into what you're doing; what those tradeoffs are when you bring on outside capital. 

Kelley: Yeah. So in my case, I was lucky in the beginning to de-risk this concept by being an intrapreneur first, right? If you just walk it backwards. But the decision to go venture-backed, um, was really because. You know, I was too nervous to both take the risk to jump out of a C-suite position when I was the breadwinner and put in our savings, right? Because it was also COVID. I mean, who knows what was going to happen, right? Were we putting cash under our mattresses? What are we, what were we going to have to do? 

I think the trade off of bootstrapping versus venture capital, or there are pros and cons of both. When you bootstrap, you're in control of your company. You're not usurping any of the mission, the purpose, the decisions that are made, um, who you hire. I think when you move over to venture capital, you do give up the autonomy that you might have. You're now making decisions by committee. You may want to hire someone and your investors aren't in favor of it.

And, you know, in the worst case scenario, depending on how you structure your board and you structure those agreements, if you don't set that up properly, you could get ousted and all of a sudden you're out of your own company. And so I think understanding these risk rewards, obviously when you take venture capital, you're not putting your family at risk. You're not taking money out of your savings, but you are giving up some of that control. 

So I think when you make the choice to go to venture capital, You are marrying these people. You need to put a ton of due diligence into that. You need to have character references and references from other founders. And even then you cannot necessarily prevent everything. It's just, I think going in with your eyes wide open was some of the message of my book. 

Allison: You ended up, you had a successful, uh, end. Quote unquote to the company in the sense that you were acquired, you would eventually be acquired by service.

Now I'm skipping over a lot of that messy middle of getting from raising the money. There's a lot of things that happened in between that, but I also want to talk about your book and some sort of accelerating to the, the end quote unquote, which is you get acquired. You are still at ServiceNow, In all of that and the ups and downs, people will have to read your book to hear more about those stories.

There were a lot of great stories in the book. What role did motherhood play in how you made decisions or moved through this world that so rarely has mothers and women more broadly in the position that you were in?

Kelley: You know, I think when you're a mom. Um, or any parent, I'll say even dads, but when you're a mother, the priority that your family takes above all things, kind of removes you from the ego of everything being about your professional success. It's not about you anymore, right? It's about the big picture of the family. 

And so when ServiceNow knocked on my door, I was very fortunate that it came inbound to me. That it was the dream exit, not just an okay opportunity. But yes, certainly in the back of my mind, I was thinking about the safety and security of my family. I mean, we had a Series A locked up. We could continue to play that game as a point solution out there and fight for funding. 

But on two levels, both the strategic ability to be successful, the best tradeoffs were to go and be with ServiceNow, technically for the product, but also for my family, because I could go back into a situation where I could see my mission through, but I could also be in the safety and security of a larger company. And so, and that it was going to be a win, win, win across the board, a win for my shareholders, a win for my family, a win for the employees and a win for ServiceNow.

I talk about superpowers in the book. I think women have a unique ability to manage all of those tradeoffs really well, and not let your ego get into it where you're like, I got to hold on to something that I created just because it's…you know, it's me laying across the table. No, it's not. There were so many other factors to consider. And obviously, As a mom and running the family, that was the primary consideration.

Allison: So now you're at service now and you decide to write this book. Why? 

Kelley: So I wrote this, I mean, first of all, this was so cathartic for me. I mean, You don't go in and do a startup certainly at 50 years old…at any age, but certainly at that age, if it's not for the faint of heart, right? This, this was, this is a very difficult thing to do under all those conditions. It was very cathartic to actually write the book and kind of walk through the emotional ups and downs again. 

But the the primary objectives for the book, there were three: one, to really encourage innovation from female innovators inside and outside of a company. So whether you're an intrepreneur or an entrepreneur. 

Second, to push more funding, ignite more funding into female founders by investors, both large funds, small funds. Angels, institutional investors, like just to really put them and encourage them to, to fund women. 

And the third was to get women to support each other. So many times we have this spirit of competition versus cooperation and collaboration. And I believe we'd be running the world if we actually figured out how to support each other.

There's one quote in my book from another founder who says, there are the women that reach down and pull the other up the ladder. And then there are women that pull the ladder up behind them. I think we want the type of women that really help each other. 

And I have a mantra that I share with everybody. I have a little sticky note on my bathroom mirror that says lift up one other woman every single day. And that is. You know, making introductions to potential customers or investors, connecting them to other people or talent that might work for them, giving them mentors or sponsors, any advice, anything that you could do to lift up another woman, if all of us just help one woman every single day, I mean, that would make a huge difference.

Allison: I, I can't help but think about, as you talk about this, the story you shared earlier in the book, where an investor told you that you needed to add more men to your team and to your leadership team. And so as you're talking about this, I'm, I'm thinking through why, what you say is so important because of that bias.

Because there aren't systems and norms right now that are supporting women, especially in this startup space. Um, so I don't know. I just, I was struck by that as you were talking about what you wanted to get out of this book and then thinking about your personal experience, what did you say when you were told to add more men? Like, how did you feel about that? I don't even know how I would respond. 

Kelley: My visceral reaction, which I was very good at not showing, was sort of how dare you say that…that a team of women can't be as good. But I think in, and I also say this in the book, the reality is diversity goes both ways. I think having both men and women on your team is important because everybody has something to add. And I wouldn't even put it on gender. I would put it on skills and capabilities and ways of thinking and knowing how we will both interact with different customers will resonate with, with different members of the team.

So diversity is important across the board, but they were trying to talk turkey with me. I think in some cases, at first blush, it sort of feels like, you know, a punch to the gut. In reality, they were just kind of telling me that we do have bias in the world still. And if you want to go for funding, having a male on your team is going to be really important. And so that's kind of…I learned to live with the reality while I work to change the reality at the same time.

Allison: You spoke to a lot of other female founders to write this book. What are you hoping, who is the audience for this book and what are you hoping that they do? 

Kelley: So there's, there's actually multiple audiences for this. My backstory is that my mom in midlife changed her entire career. She went from, you know, being a sedentary accountant to a law enforcement officer in one of the toughest academies in the country. Because in her day, they weren't allowing women into the police force. And then, you know, they had changed that ruling. And so she went for it and she was a great example of going for it. Unfortunately, she lost her life in the line of duty. And I think that that impacted me greatly about sort of carpe diem and do everything you can and don't have limiting beliefs.

And so I wanted to encourage women that were out there thinking they cannot do this, or time has passed them by, or they're 50, I mean they're set in stone now, they can't go do a startup, that that actually wasn't true. 

So if you're sitting on a great idea, the world needs your great idea, go for it, just find your channels of people like me and like you to help, help you get that off the ground or encourage you.

I think I wanted to reach investors and make sure that they understood that funding women is probably going to be the best thing for their fund. I mean, the data is out there that says that a lot of female founders are producing some incredible results inside these funds. 

And, you know, existing female founders, when you're feeling like there's all doom and gloom or you're in the low points, you're getting rejected from customers or investors. There is a light at the end of the tunnel and that there are people that have experienced that out there and that they could still be successful. 

So part of my story is that, or seeing themselves in any one of these 30 founders that I interviewed, through different ages and cultural backgrounds and industries, they would find themselves in these women.

Allison: I certainly loved the book. I mean, I saw myself throughout so many of these stories. And so I can definitely vouch for the fact that as a female founder reading, I found a lot of value in that. But I also thought that anyone who's considering a big career pivot, even if it's not entrepreneurship, there's a lot that you can learn in this about how to take calculated risks. So it definitely, to me, was not just for female founders or even just for investors. I think there were a lot of really good stories in there.

I'm curious, as you were researching this book, what was most surprising to you? What did you learn from speaking to these founders that was most surprising?

Kelley: Well, number one, despite different ages, I mean, 70 down to 28, like that they had experienced all the same things, even though there were generational differences, right? Time, technology has changed. I think the fact that we're still finding it difficult to get funding is another one that was like a big surprise and probably the biggest surprise was that if you started with female investors in your cap table from the very beginning and you pursued only female investors, your chances of getting funding later were actually quite diminished and further rounds, like that was that research, that data really, really shocked me. So I'm not sure why that was right. That was a really shocking revelation.

Allison: You mentioned helping one woman per day. I have to imagine that there are a lot of women who are clamoring to get your advice or your mentorship. What advice do you give someone like me who is much earlier in my journey than you are right now?

You’re now post-acquisition with ServiceNow, what would you say to me? I know that's an impossible question to ask you, given that you don't know a ton about me, but from the perspective of being an exited female founder, what are the two cents that you could offer me today? 

Kelley: I think that you need for yourself to define success. I think we feel compelled to define success as an exit or, you know, we made tons of money, and I think success needs to be defined personally by you. 

For me, it was so much about my mission. It was so much about getting this technology into the world and seeing the best fulfillment; it was seeing people completely able to change their careers because they got experience and exposure outside their typical day jobs.

It was like they were unleashed. They were free. 

And so whatever success is to you, even if your startup, you decide to shut it down or it doesn't work out. You need to have those success metrics for yourself. You don't even have to share them, right? Because obviously investors may just want to make gobs of money, but what are those success metrics for you? Because it will help you know What type of risks you're taking and when and why, because you've got your own scoreboard. 

Allison: I love that. Last question for you. As you look out to the next year, what does success look like for you? What are you most excited about? 

Kelley: So for me, and sort of outside what I'm doing at ServiceNow, it's really that I've had all these female founders come to me and say, Hey, thank you for having such an impact on me in some way. Thank you for helping me through that really difficult period. Thank you for introducing me to that investor. Thank you for opening up a new channel for revenue by making those introductions to potential customers. That is really, I feel like that's my legacy. 

And I think you know, for me having a legacy, maybe it's my age, maybe it’s where I am in my life, but I really wanted to do something positive for other women. And writing the book was part of it. And now helping put your money where your mouth is, putting your advice where it should be, and giving back. So that's, that's really what, what I'm hoping to do and now and into the future. 

Allison: Wonderful. Well, thank you so much for your time today. I very much enjoyed reading the book.

I think that. Any person who is thinking about a big career pivot, especially if they're thinking about intrepreneurship or entrepreneurship more broadly could learn a lot from this book. And so we will link out to it in our, uh, podcast notes and really appreciate you sharing all of these stories and the advice today.

‍Kelley: Yes. And thank you, Alison. And as I always say to every entrepreneur, keep on dreaming. Keep the dream alive. 

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