Scaling Leadership: Takeaways from the 2026 OVF CEO Summit
October 2026
Matt Compton
Leadership is a skill of its own that is increasingly critical with every stage of growth. That idea framed this year's Oregon Venture Fund CEO Summit. On September 17, 40+ current and exited Founder CEOs from our region gathered at Amaterra Winery for an afternoon on our theme: Scaling Leadership.
We host the Summit each year so CEOs can sharpen their craft in an informal, peer learning environment. Our goal is simple: every venture-backed CEO in the region should have a set of founder CEO peers they can lean on for practical, actionable wisdom on their hardest challenges.
The afternoon had three parts: a fireside chat with Mary Beth Laughton, CEO of REI Co-op; short "CEO Hacks" from founders in the room; and small-group sessions focused on a single question. Here is what we took away.
1. Leadership is a distinct skill
We opened the day with a definition. Leadership is the ability to rally people to a cause, the character to inspire confidence, and the capacity to turn vision into reality. That is pretty close to a job description for a startup CEO.
Leadership is also a skill, which means it can be developed and improved like any other. Early on, a founder leads by doing. The CEO is the best salesperson, the product lead, industry expert and the recruiter, and the team is small enough to follow along by proximity.
That stops working as headcount grows. Results start to depend on the people the CEO hires, the clarity of direction they set, and the decisions they hand off. The approach that built the company is usually not the set of skills that scale it and the transition can feel jarring for founders.
2. Find your leadership style and own it.
We were honored to have Mary Beth (MB) join us and share her take on scaling leadership. She has led and built high performance teams at scale across some of the worlds most iconic brands. Today MB leads REI Co-op, a specialty outdoor retailer with $3.5 billion in revenue and more than 12,000 employees. She is also a Portlander.
Three key ideas stayed with us:
Listening can be more powerful than speaking. MB spent much of her first 90 days at REI listening to input at all levels of the organization. Then when she synthesized the input and rolled out their new strategy, it was based on operational reality and buy in was baked into the process.
Write down your strategy and repeat it. Create a referenceable and rememberable artifact that defines your strategy. Share it, repeat it, and enable everyone to connect their work to it.
Lots of different leadership styles can be effective. Figure out yours and own it. Not all leaders of large organizations need to be extroverts.
3. Sometimes the best leadership advice is small and specific
Between sessions, four CEOs took a few minutes each to share one "hack": a concrete practice they use to be a better leader. These were some of the most quoted moments of the day, because a hack can be tried the very next day.
Scott Clark, CEO of Distributional: "The False Positive that Feels Exactly Like Traction" Product-market fit is when users cannot get enough of the product. "Vision-market fit" is when prospects cannot get enough of you and want to keep talking. One says "I have this problem right now." The other says "this will be a big problem someday." Confusing the two can kill a start-up. A CEO needs optimism but cannot afford to fool themselves. Scott’s test: ask yourself, "Do they like the product, or do they just like talking to us?"
Allison Persitz, Founder and CEO of Hubb (acquired by Intrado): "Building the Future, Missing the Present" CEOs are great at planning for the future, and that strength can steal the present. Allie spent years telling herself she could relax once she got "there": the Series B, the CFO hire, the exit. Then she got there and found that "there" thinking is a habit and not a destination. Talented people want to follow leaders who are present and lead from a strong foundation. Allie dedicated purposeful time to find clarity, define values and establish purpose, both for her as an individual and for her company. Allie’s advice: avoid chasing the belief that life doesn’t begin until you arrive. There is no eventual 'there.' There is only here.
Kim Malek, Co-founder and CEO of Salt & Straw: "The Golden Hour" Elite athletes don't leave peak performance to chance. Why should CEOs? Kim believes that consistently showing up at your best requires intentional training—not just for your body, but for your mind. Her secret weapon is “The Golden Hour”: one uninterrupted hour, starting at 4:45 a.m., dedicated to preparing for the day ahead. She combines three powerful practices: gratitude to build perspective, focused learning to fuel growth, and intense exercise to build physical and mental strength. It's a daily investment in herself so she can show up at her best for everyone else.
Tim Delisle, Co-Founder and CEO of fiveonefour: "Throw out your IC playbook. Everyone is a manager now" AI agents are putting individual contributors through the transition every first-time manager faces, from owning the work to owning the outcome. "The agent did it" does not get anyone off the hook. Tim's point is that the playbook already exists: define the outcome, set checkpoints and own the result. His challenge to the room: take your first-time-manager training and give it to someone managing AI agents.
4. CEO Peers are often the best advisers.
The longest block of the day went to one question: what is your biggest current leadership challenge? CEOs split into small groups, matched roughly by company scale and in some cases by industry, and spent an hour on it.
The format was deliberately simple. Everyone took a few quiet minutes to write down their challenge, then had about 90 seconds to say it aloud with no discussion. Each group then picked the two or three challenges with the most energy and dug in.
A few themes came up across groups:
AI tools are amplifying the 10x employee effect. How do CEOs and functional leaders identify and recruit these 100x AI powered talents and turn them loose.
Growth stage companies that were founded pre-AI now face the same innovator’s dilemma historically reserved for mature companies. Adaptability and willingness to change or even throw out something that was working 12 months ago are critical leadership traits today, even for relatively early stage companies.
Influence leadership can be as important as direct leadership. Especially for companies in the semiconductor, healthcare, and payments spaces with complex ecosystems and multi layered supply chains. CEOs need to be seen as leaders in their industry and have the ability to bring (often much larger) ecosystem partners into their vision of the future.
Thank you
Thank you to Mary Beth Laughton for an honest and generous conversation, and to Scott, Allie, Tim and Kim for sharing their insightful hacks. Thanks as well to all the Founder CEOs who brought a real problem to the table or provided a colleague with some practical wisdom on their challenge. You all have some of the most difficult jobs out there and we thank you for all you do!