The Fractional Interview Series - Chris Bee, Fractional Chief Technology Officer

We’re back with a new episode of Fractionally Speaking. It’s a rapid-fire Q&A, 5 minutes long, featuring the top fractional executives in tech. Get an inside peek into how the best approach their fractional work.

Today's 5-minute Q&A features Chris Bee, Fractional CTO. He was previously the interim CTO at Superhuman, CTO at Lessen, and Eng Leader at Uber, Zillow, and more.
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I asked him questions like:

1. "How did you land your first client?"
2. "How are you adding value to your clients on a fractional basis?"
3. "How much time do you commit to your fractional clients versus side projects like DevPlan?"
4. "What’s one thing you wish more founders and hirers knew about fractional work?"

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The Interview

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Taylor: When did you first start doing fractional work?
Chris: I dove into fractional work in 2023, right after having a successful exit from Lessen. It was a crazy ride there in the hyper-growth startup phase. We went from a seed valuation to a $2 billion valuation.

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Taylor: And what’s your fractional one-liner?
Chris: I work with early-stage startups in the seed to Series A range, helping teams primarily with people, process, and product.

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Taylor: How did you land your first client?
Chris: My very first client I actually met at a kid’s birthday party.

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Taylor: How many clients are you working with right now, Chris?
Chris: I’ve got two. One in PropTech and the other in the AI platform space. I also advise two companies, one in health tech and the other in prop tech.

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Taylor: Tell me about your time commitment with your fractional clients and advisory roles.
Chris: It varies a bit by agreement, but generally, I work out a set number of hours per week and use that as an average. Some weeks are higher, some are a bit lower, but I have a consistent amount that I stick to each week.

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Taylor: Do you have specific days or times dedicated to each client, or do you work throughout the whole week?
Chris: I like to structure it where I have a couple of days where I’m essentially fully available and other days when I’m more intermittent. I’ll still respond to Slack or email, and if there’s a critical meeting or interview, I’ll take that. But generally, I focus on a couple of days where I’m really present and not juggling other things. My fractional clients and my work on a product called DevPlan (DevPlan.com) take priority on those days.

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Taylor: How do you balance your work with DevPlan versus your fractional work?
Chris: It’s split pretty evenly now. It depends on the week, but I tend to work on DevPlan during nights and weekends. For the normal working week, though, it’s pretty well balanced.

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Taylor: Take one of your clients, how are you adding value on a fractional basis?
Chris: One company I’m working with, I’ve helped with hiring their initial team, onboarding, and ramping them up. I do one-on-ones with the team, helping with career growth, mentorship, and ensuring everyone stays aligned. In these smaller companies, I play a role similar to a PM or engineering manager, a cross-functional role. And fundraising is another big area where I help.

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Taylor: What’s one thing you wish more founders and hirers knew about fractional work?
Chris: A lot of companies could actually get a much higher caliber of executive than they could afford for a full-time role. With fractional work, you can bring in someone seasoned and experienced who may not have joined otherwise.

Taylor: The two clients you're working with now are benefiting from your impressive background, but they might not have the need or budget for a full-time hire.
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Taylor: One last question, what’s your why? Why do you do fractional work?
Chris: It feels great to apply everything I’ve learned over the years where it’s really needed. That’s the big “why” for me. But I also love the variety—I get to pattern match across a lot of companies and form strong opinions on what works and what doesn’t. Lastly, I love the independence. It’s more of an open, transparent relationship. You’re not working for someone; you’re working for yourself, setting your own pace, and doing the most important and valuable work for the company. That’s what you’re evaluated on. The new fractional world is really fulfilling for me in a lot of ways.

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‍Fractional Jobs helps startups hire fractional talent, like Chris Bee, across about 10 different function areas. And we help fractional leaders build a successful fractional practice through our Playbooks, our Toolkit, and then through introductions, of course, to potential clients. And that’s about it for Episode 3 of this little fractional interview series that doesn’t have a name yet!