Meet the Team: Derek Harris
Tell us a little bit about yourself, background, and role. How did you land here?
My journey started at Washington State University (Go Cougs!), followed by years at AT&T and an MBA in Data Analytics from the University of Southern Indiana. I was drawn to data analytics around 15 years ago during the rise of “big data.” I got my first taste of startups at Zipwhip, leading a sales team that tripled revenue in 18 months through a Series C round and eventual acquisition. After roles in FinTech, recruiting tech, and GTM consulting, I landed at Trestle.
I was referred to Trestle by a former boss through Tom Maddock. A quick check with local friends confirmed that Trestle’s products were “top of the line,” which was all the convincing I needed to talk with the co-founders.
I never originally saw myself in sales. Years after college, a former restaurant owner pointed out that I’d always treated my bartending job like sales: upselling guests to higher-quality options to give them a better experience. That customer-first focus made the transition to sales feel completely natural. Plus, I love the clarity of go-to-market roles, where success is directly tied to revenue metrics.
What does your daily routine look like?
Because we are growing so fast, a huge portion of my days recently is spent interviewing, reviewing candidate notes, or planning interviews. Staffing up our team is currently our single biggest opportunity.
Now that we’ve started hiring, the other major focus of my day is training, development, and coaching. I want to spend quality time with our new hires to make sure they have a great onboarding experience, have fun learning, and enter our sales cycles feeling genuinely jazzed and ready to go.
There are also the day-to-day operations, including pipeline reviews, one-on-ones, and helping deals get over the line, which usually means stepping in when there’s a sticky point. Sometimes legal redlines come up, pricing objections happen, or a customer needs an extended data test (which is where Will Lewis comes in). What’s fantastic about Trestle is that it is truly an all-hands-on-deck environment. We are not a siloed organization; everyone pitches in to help get these deals done.
What excites you most about Trestle?
It is absolutely the product! Having a product that is truly best-in-class is a rare and exciting opportunity for me. In my past roles, I rarely had the best-in-class product, which meant always trying to find the narrow niche of what our product did best and focusing strictly on that. Here, because our product is genuinely good, we love running data tests against competitors. When competitors are involved, we welcome it: “Bring them all on, let’s test against everyone and prove it.” In seat-based SaaS, “who is best” can be highly subjective. But in our world, it is highly objective: did we deliver on what we promised or not? I love being able to prove that value clearly to our customers.
What Trestle value do you relate to most?
I relate most to Figure It Out. This is a mindset I look for and hire for specifically, focusing heavily on curiosity. When candidates ask me about career growth opportunities or what the culture is like at Trestle, I usually flip the question back to them. I explain that we are a small company where everyone is highly important. So, what are they going to bring to the culture? What opportunity are they going to create for themselves? We aren’t looking for people who want to hide; we are looking for people who challenge us and want to make the organization better.
What’s one surprising thing that helps you do your best work?
As a people manager and leader, I have always considered myself “overhead.” I tell my teams that if I cannot help them be successful, there is absolutely no reason for my role to exist. I discovered this philosophy in my late 20s or early 30s while working in telecom. A coworker and I were having beers one night, debating the “purpose” of our roles. We realized that what truly felt the best was investing energy into our teams and watching them succeed, get promoted, or even get recruited to higher roles. Hearing from someone three years later saying, “Hey, I got promoted again, thanks for all your mentoring,” is incredibly impactful. Steering people toward the goals they have set for themselves is what gives my role genuine purpose.
When thinking about an effective workplace culture, I don’t look at us as a “family.” It’s hard to coach your siblings or parents, and those dynamics don’t translate well to a professional setting. Instead, I view an effective culture like a high-performance sports team or an acting troupe. Everyone has to hone their individual craft and be great on their own, but they must absolutely engage and work together to win. Our success comes from how well we collaborate as a team.
What’s a topic you could give a 5-minute impromptu talk about?
If it’s work-related, I could easily give a talk on building trust in workplaces. I’ve done this with many teams over the years, and it’s heavily based on the book The Speed of Trust by Stephen Covey. While the book has a lot of details, the core concept is incredibly simple: when people repeatedly follow through and do what they say they are going to do, trust is built. Covey uses the analogy of “trust deposits” in a bank. To me, it’s about being relentless about your commitments. When you build that level of trust, your coworkers don’t have to spend time following up with you, which means business moves significantly faster.
If it’s non-work-related, I have a ridiculous, highly focused knowledge of ski resorts. I know resort elevations, how much powder they get, and the best months to ski them across the globe. I love looking at maps, zooming in on topography, analyzing snowfall patterns, weather, the pitch of the terrain, the length of the runs, and the après-ski scene (in that exact order!).
