Interview with Kristen Hamilton, Staircase Ventures Advisor, Serial Entrepreneur, and CEO Coach, on How Founders Become Great CEOs

The Advisor Series – Featuring Kristen Hamilton

At Staircase Ventures, we believe that one of the best ways to support founders is by surrounding them with experienced advisors who have been in their shoes. One of our advisors, Kristen Hamilton, is a serial entrepreneur, investor, and CEO advisor who has built and scaled multiple successful companies. 

Kristen co-founded Onvia, leading it to a successful IPO on Nasdaq, and later co-founded Koru, a leader in predictive hiring software, which was acquired by UK-based Capfinity. Today, she’s a professional advisor to startup CEOs,  teaching founders how to be great CEOs and how to navigate the challenges of building and scaling their companies. She has also been on the boards of Top Hat, Aduro, Strivr, and Fairmatic.

We sat down with Kristen for a conversation about the biggest lessons she’s learned as a founder, CEO, and advisor.

Q: What was it like starting Onvia so early in your career?

Kristen: “It was exhilarating and terrifying. We had no freaking idea what we were doing, but that was actually a good thing in a way. We didn’t know what we couldn’t do, so we just went for it. We were students of the tech industry, we studied every company we could, and we were incredibly scrappy.”

“A key lesson I learned early on was audacity matters. If you believe in what you’re building, and you’re willing to throw yourself at it completely, people will take notice. That being said, audacity alone won’t get you there. You also need to be relentlessly pragmatic and willing to do whatever it takes to make those first sales, find product-market fit, and scale.”

—

Q: Onvia went public during the dot-com boom. What did that experience teach you about market cycles?

Kristen: “It taught me that growth trumps everything – until suddenly, profitability matters more. We went public in February 2000, just ten days before the all-time high of the Nasdaq. At the time, the only thing investors cared about was rapid growth. Then the market crashed, and suddenly, companies that weren’t profitable were in deep trouble.”

“I’ve seen the same cycle play out again and again, in 2008, 2021, and even now with AI. Investors chase hypergrowth – or just hype – but at some point, the focus always shifts to fundamentals. The best founders don’t get caught up in market hype. They build sustainable businesses that can withstand cycles.”

—

Q: You’ve raised venture funding multiple times. What do founders get wrong about fundraising?

Kristen: “First of all, founders need to learn how to fundraise. There are right and wrong ways, and doing it the right way gets you a term sheet. The biggest mistake after that? Chasing the highest valuation. Founders think a sky-high valuation is a badge of honor, but it can actually be a trap. If you raise at too high a valuation and don’t grow into it, your next round will be painful. Down rounds suck. They demoralize your team, make hiring harder, and put you in a weaker negotiating position.”

“The best founders think about fundraising strategically. They ask: ‘How much do I need to hit my next milestone? Who are the investors that will truly add value? How do I optimize for long-term success instead of short-term boosts?'”

—

Q: At Koru, you built a predictive hiring platform. Given the insights you gained building the company, what are the biggest hiring mistakes founders make?

Kristen: “First, they hire based on credentials instead of competencies. I see so many founders get excited about someone with a flashy resume—Stanford MBA, ex-Google in their LinkedIn bio, etc—but that’s not a predictor of success. What actually matters is grit, curiosity, adaptability, and ownership. Those are the traits that make someone thrive in a startup.”

“Second, they hire execs for the wrong stage. The best hires are those who can drive great results at the stage you are currently in and maybe the next phase of growth as well. But hiring a CMO from Pepsi for a Series A company will almost certainly fail.” 

“Finally, on a related point, they wait too long to fire people. A bad hire is incredibly expensive. Not just financially, but culturally. If someone isn’t delivering, or worse, if they’re toxic to the team, you have to act fast. The longer you wait, the more damage that can be done.”

—

Q: What are some underrated skills that make a founder a great CEO?

Kristen: “One of the most underrated skills is the ability to listen with curiosity. Founders are often passionate and opinionated (which is great), but the best ones know when to shut up and really listen—whether it’s to customers, employees, or investors (sometimes). They don’t just wait for their turn to talk; they absorb information and use it to make better decisions.”

“Another underrated skill is emotional resilience. The startup journey can be brutal. You’ll have amazing highs and crushing lows, often in the same week. Founders who can stay level-headed, bounce back quickly, and keep their teams motivated through tough times are the ones who make it.”

—

Q: What’s a common early-stage mistake founders make when building their companies?

Kristen: “They fall in love with their product instead of the problem. Too many founders start with a solution and then try to find a problem for it. That’s backwards. The best companies obsess over a real, painful problem and iterate their way to the right solution.”

“Customer discovery never ends. Even when you think you have product-market fit, you need to keep listening, testing, and evolving. The worst thing you can do is assume you ‘figured it out’ and stop talking to customers.”

—

Q: What should founders understand about the transition from founder to CEO?

Kristen: “When you start a company, you do everything. You’re in the weeds, selling, hiring, building, putting out fires. But as the company scales, you have to be very selective about where you get into the details. You have to build and lead a high-performing team. That’s a hard transition for many founders.”

“Great CEOs hire incredible people, delegate, and focus on the highest-leverage decisions. Sometimes, they need to go “founder mode” to resolve something. However, they don’t micromanage the business or team. It’s a skill set you have to develop. A rule of thumb is – only do the things that only you can do. The best founders I work with at Enjoy The Work are the ones who actively work on becoming great CEOs—they read, they get coaching, and they’re constantly learning. They become comfortable at the edge of their comfort zone.”

—

Q: If you could give one piece of advice to a founder starting a company tomorrow, what would it be?

Kristen: “Don’t do it alone. Even if you have a co-founder, get an advisor, a coach, or a mentor who has built and scaled companies. There are so many avoidable mistakes in startups, and some of them can kill your company. A great advisor will help you see around corners, stay focused, make better decisions, and avoid the most common failures.”

“And remember: founding a startup is a marathon, not a sprint. Take care of yourself. Surround yourself with people who will push you but also support you. The journey is brutal, but if you do it right, it’s so incredibly rewarding.”