ServiceNow’s Kelley Steven-Waiss: 5 Things I Wish Someone Told Me Before I Became A Founder

As part of our interview series called “5 Things I Wish Someone Told Me Before I Became A Founder”, I had the pleasure of interviewing Kelley Steven-Waiss.

Kelley Steven-Waiss is a chief transformation officer at ServiceNow, helping customers drive workforce transformation. She previously served as head of workforce innovation at ServiceNow and was the founder and CEO of Hitch Works Inc., an internal talent mobility platform acquired by ServiceNow in June 2022. Kelley brings more than 25 years of executive management experience, with 13 years as a chief human resources officer in technology. She also serves on the board of FormFactor, Inc.

Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?

I got into HR by happenstance. After working on strategic planning for a finance organization in the semiconductor space, they asked me to interview for the CHRO role. I declined a few times, but eventually said yes.

Even though I had some hesitation, I realized that I had so many skills appropriate for the role, especially the change management background and experience with turnarounds, corporate strategy, and culture transformations. Having a discipline for managing large-scale change really made a difference. It wasn’t my intention to become a CHRO, but it ended up being my career path for 13 years.

It’s a similar story of how I become a founder. I witnessed so much attrition and talent leaving organizations because they weren’t feeling seen, valued, or heard. They weren’t able to pursue their chosen career paths or ended up being typecast into their current role. I knew that we had so many skills and capabilities buried beneath the surface, and there had to be a way solve this if we could visualize the data and scale a solution across the organization. When I couldn’t find a technology that could solve for what I envisioned, I ended up taking things into my own hands and whiteboarding it myself. After speaking about the successes I was having with this type of tool internally in several HR forums, it was clear this solution needed to be commercialized.

There was no doubt this problem was not just in my organization, but there was also a huge gap in the market. I’ve always felt I’ve had a “jungle gym career”, so it’s not such a coincidence that I would end up building software to help other people pursue their jungle gym career paths.

Can you tell us a story about the hard times that you faced when you first started your journey?

I’ll use an example for how I ended up securing venture capital. I started as an intrapreneur first (incubating my solution as a subsidiary inside of a large enterprise). Although it was a valuable tool and was driving high engagement and saving the company money, once the Covid-19 pandemic hit, the company had to re-prioritize spend and my Hitch investment was going to get cut. Having never raised money in my life I was suddenly faced with the prospect of raising venture capital within sixty days, or the business would be shutdown. So not only was I attempting to spin out a business, but I also had to raise the capital and get all twenty-five people in the subsidiary Hitch to follow me.

I was the CHRO at the time I started Hitch, and none of us knew how to manage through a pandemic. Likewise in the venture world, deploying capital when you can’t meet the founder face to face was a new concept. A little bit of this was being fearless; not being with without fear, but just being courageous, stepping forward, and being willing to lean into something you’ve never done before.

Where did you get the drive to continue even though things were so hard?

The fire beneath me really came from my mother who died tragically when she was still very young. She always wanted to be a police officer, but in the 1960’s women were not allowed to serve. When they finally allowed women into the force, she went into the Academy at age 45 and really did something close to impossible. She went from being a sedentary accountant into the physical rigor of the Academy and passing the Los Angeles Police Department test — one of the most difficult in the country alongside New York and Chicago. She died doing something she loved, even though the odds were stacked against her. I did not want her death to be in vain. She was a great example of being fearless and facing the prospect of the impossible by having believed in herself.

So, how are things going today? How did grit and resilience lead to your eventual success?

In 2022, my company Hitch Works got acquired by ServiceNow, a top cloud computing platform company. I knew I couldn’t change the world as a point solution, and now had the power of a proven platform to bring my technology to more customers It was a dream come true to have my vision come to life to make work better for people.

You must have a strong center as a founder because you’ll get rejected multiple times from investors and customers. What keeps you going is your passion, patience, and perseverance for what you believe your technology, product, or service can do for the world. For seven years I woke up every day with a mission and purpose, which was how to make work better for people. I believed my company’s technology would have significant outcomes for organizations, but it would also allow people to be seen, valued, and heard. That really kept me going through tough times.

The one thing I didn’t feel as an executive, but I did feel once on the other side as a founder, was the weight of responsibility for the overall success of the company. When you’re a CHRO, you don’t worry that your large enterprise company will make payroll, it’s more of a distributed responsibility across the team. When you’re a founder, you worry about cash every single day because it’s not only affecting your employees, but also dozens or more families. You must be prepared for the awesomeness of that responsibility, and it was something I’d never felt before.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One thing I learned was the importance of having awareness for customer product sensitivity when working in the tech space. It’s not a deal-breaker, but not the best optics when you conduct a customer call using a competitor’s meeting platform!

We all have those early pandemic stories of trying to balance work and home life interruptions. Things like trying to wave off my daughter asking me to brush her hair while pitching an investor, or a fire alarm going off in the middle of customer pitch, or frantically trying to delete the baby shower Zoom background as I started a customer call. Things that certainly seemed embarrassing at the time and now seem relatively normal in a post-pandemic world.

What do you think makes your company stand out?

When you start a technology company, it’s because you believe it will ultimately change the world. This is why it really made sense for Hitch to become part of ServiceNow, as changing technology from a point solution into a platform is a completely different value proposition. ServiceNow has over 8,100 customers, so putting Hitch’s skills intelligence functionality into the Now platform can really serve many more employees and affect more people’s lives. It’s making work better at a scale that could not be done as a startup.

There are so many hidden figures in an organization when it comes to talent, and leaders need to create a dynamic, digital way to excavate those great skills and match them to the right opportunities. Traditional job architectures need to be automated and tied to skills, which is where ServiceNow comes in. We make sense of all the skills data silos, and we navigate to create a single source of truth. AI is truly a game changer here, helping these systems communicate with each other to empower a unified experience of skills.

As people learn, unlearn, and relearn throughout their careers, technology can enable learning within the flow of work in a customized and personalized way, all on a single platform with ServiceNow.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I learned the importance of taking breaks. When you’re leading a startup it can get exhausting, you wear so many hats and the pace is so intense. You’re the chief sales officer, head of HR, chief product officer, and the head of finance — all at the same time. In the beginning you don’t have the money to hire for all those roles, and you’re covering a lot of ground, so I can’t emphasize enough the importance of pacing yourself and taking the breaks every quarter. It can just be logging off for the weekend or taking one mental health day. Once you’re successful, you can hire other fantastic people around you to take some of the burden off.

Physical activity is another important one. The pandemic added complexity for going to the gym or workout classes, but one thing I tried prioritizing was making use of “walking meetings”. This is great for your one-on-one meetings, and make sure to tell your people they should walk while you walk. Not only did it make me get up from behind my desk, it made me think better.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I have immense gratitude for so many people, but I will call out Brian Lent, a serial entrepreneur. He was the CTO at a former company where I was the CHRO, and he became a fast friend after we acquired his company. I was immensely grateful for the time Brian spent sharing the realities I would face as a founder.

While I was preparing to do major fundraising, he coached me on something called the “rude FAQ”, which was building a list of the most challenging and pointed questions an investor could ask me about my company. He prepared me to answer those questions, and how to identify other team members who could take those questions during a call. That was of immense value to me because I was well prepared for the difficult questions.

How have you used your success to bring goodness to the world?

I wrote a book called “Valley Girls: Lessons From Female Founders in the Silicon Valley and Beyond,” because I wanted to share the journey I’d been on as a founder as my way of paying it forward. These stories provide the raw accounts of what it was like to be a female founder and lessons I learned.

I also do tremendous amounts of coaching for other female founders, and recently got contacted by a couple of founders seeking advice as they went into a fundraising round. These aren’t paid positions, but a way to volunteer my time and experience to help other women who may need a sounding board. I have built a personal board of directors around me of people who have capabilities and learnings beyond my experience, and they help me when I need it most. It can be a very lonely position to be a founder if you don’t have these support systems, so acting as a mentor is my way of giving back.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

1. I’ll restate the importance of making time for a break at least once every quarter. It’s up to you to decide what works best, if you need a weekend to unplug or taking a mental health day to spend time with your friends or family.

2. You’re running a marathon, not a sprint, so know how to pace yourself and your team. If you’re like most people and running along at sprint pace, you’re probably not going to make it the full distance. You will wear a lot of hats and the list is never done, so recognize when to give yourself a break and pace your team so no one burns out.

3. You’re not just selling to customers — you’re selling to investors and your employees ALL THE TIME. Keep your spirits up, bring the energy, and constantly keep the enthusiasm for what you’re doing.

4. All money is not created equal, so pick your investors wisely. When you raise capital and take on an investor it’s like a marriage, so there will be good times and bad. Is this somebody you’re willing to call in the bad moments and feel like they’ll support you? It’s important that they are willing to share advice or make introductions to potential customers.

5. Perfectionism is the death of a startup. Make sure to build a strong muscle to experiment and iterate, since that is the only way innovation can thrive. You need to get a product into the world that’s good enough to get feedback and keep making it better with time. If you have a tendency for perfectionism, keep yourself honest and put people around you that don’t let you get away with it. Hire a great chief product officer that’s willing to iterate, innovate, and get a product or solution out the door fast.

Can you share a few ideas or stories from your experience about how to successfully ride the emotional highs & lows of being a founder”?

One of the biggest issues I faced was imposter syndrome. I was building a software company, but I wasn’t a serial entrepreneur or an engineer. There are moments when you’ll get rejected from a customer or an investor, and you let the narrative creep in that says you’re not good enough. You really need to take care of your mental health and remember that the positive dialogue you have with yourself is important. I went through a rough patch when facing multiple rejections for fundraising after the initial round. That is the time when you must dig deep and reach out to that personal board of directors.

I spent a lot of time telling myself why I couldn’t do something or why I wasn’t worthy of an opportunity. When I started to change that self-dialogue to “why wouldn’t I go for that?” and “there is no reason why I shouldn’t be able to achieve that,” it changed my life. It also helps to get feedback, seek input on how to up your game, and be the constant learner. Everybody goes through imposter syndrome, and it’s really important to understand that you can’t be good at absolutely everything across the board.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

My goal is to help female founders get the funding they need, since the numbers are still so low. The movement I want to create is to build awareness about why female founders make great entrepreneurs. Women generally have a ton of empathy, which is what human-centered design is based on. If we can use that superpower to be in tune with the products and services people really need, it’s a huge leg up. That’s the movement I can help stimulate.

How can our readers further follow your work online?

You can find me on LinkedIn and X talking about skills and talent transformation. If you’re looking for great insights from a group of women leaders, check out my new book “Valley Girls: Lessons From Female Founders in the Silicon Valley and Beyond”. I hope this helps inspire all you future leaders to take the next steps in your career journey!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About the Interviewer: Douglas E. Noll, JD, MA was born nearly blind, crippled with club feet, partially deaf, and left-handed. He overcame all of these obstacles to become a successful civil trial lawyer. In 2000, he abandoned his law practice to become a peacemaker. His calling is to serve humanity, and he executes his calling at many levels. He is an award-winning author, teacher, and trainer. He is a highly experienced mediator. Doug’s work carries him from international work to helping people resolve deep interpersonal and ideological conflicts. Doug teaches his innovative de-escalation skill that calms any angry person in 90 seconds or less. With Laurel Kaufer, Doug founded Prison of Peace in 2009. The Prison of Peace project trains life and long terms incarcerated people to be powerful peacemakers and mediators. He has been deeply moved by inmates who have learned and applied deep, empathic listening skills, leadership skills, and problem-solving skills to reduce violence in their prison communities. Their dedication to learning, improving, and serving their communities motivates him to expand the principles of Prison of Peace so that every human wanting to learn the skills of peace may do so. Doug’s awards include California Lawyer Magazine Lawyer of the Year, Best Lawyers in America Lawyer of the Year, Purpose Prize Fellow, International Academy of Mediators Syd Leezak Award of Excellence, National Academy of Distinguished Neutrals Neutral of the Year. His four books have won a number of awards and commendations. Doug’s podcast, Listen With Leaders, is now accepting guests. Click on this link to learn more and apply.