Oregon Venture Fund CEO Summit 2025: The CEO Hackathon

October 2025

Matt Compton

This year’s Oregon Venture Fund CEO Summit brought together the region’s leading venture-backed CEOs for a day of high-impact learning and candid exchange. The theme “CEO Hackathon” captured the spirit of the event: a fast-paced, peer-driven forum where founders shared practical ideas and real-world insights to help each other scale smarter and lead better.

Keynote: Building a Company You’re Proud Of

The summit opened with a raw and powerful talk from Henry Shuck, founder and CEO of ZoomInfo, who shared the story of rebuilding his company after a period of unprecedented growth.

Henry described how ZoomInfo’s meteoric rise to $1.3 billion in ARR and a stock-price high led to another founding moment. He could see the company’s foundation beginning to crack - customer experience slipped, leadership alignment frayed, and pride in the company eroded. This realization was the catalyst for rebuilding - restructuring the leadership team, redefining the company’s vision, and rediscovering joy and ownership in the work.

Three key insights stood out:

1. Rebuild with Hunger and Alignment, Not Credentials.
   The best leaders aren’t the ones with perfect CVs but those whose drive, competence, and values match the company’s stage. Henry cautioned against the temptation to hire the “shiny penny” executives - the pedigreed veterans who bring old playbooks to new problems - and emphasized the importance of surrounding yourself with people who are still building toward something, not resting on what they’ve already achieved.

2. Stay Close to Customers.
   As ZoomInfo scaled, Henry found himself further removed from the customer voice. Fixing that became essential. Over the past 18 months, he’s spent roughly half his time back in the field — demoing new AI products, talking directly with customers, and observing reactions firsthand. “If you don’t know the voice of the customer intimately, you can’t lead on product, vision, or strategy.”

3. Power of No and Leaning in to Founding Moments.
   When growth is strong, it’s easy to prioritize short-term wins, but that often erodes what makes the company durable. Henry reflected on the discipline of saying no, of eliminating seemingly important initiatives until only the most critical priorities remain. “Every great company,” he said, “has a multitude of founding moments. The challenge is recognizing when you’re standing at one and having the courage to start again.”

Rapid-Fire CEO Hacks

Following the keynote, eight CEOs shared five-minute “hacks” - crisp, highly practical insights drawn from their own operating experience. The range of ideas reflected one thing all great CEOs share: a relentless curiosity about how to lead better.

Mining for Conflict.

Healthy companies surface uncomfortable truths early. Two simple questions 1) “Tell me something I don’t want to hear” and 2) “If this project failed a year from now, what would be the reason?” can unlock candor that normal status meetings never reach.

Managing Two Time Horizons.
As organizations scale, tension builds between the teams focused on today’s execution and those inventing tomorrow’s capabilities. One framework divided work into two explicit categories: Perform (operating and improving the current business) and Transform (building the next version of it). Each has separate goals, budgets, and meeting rhythms. The structure not only reduced internal friction but gave teams renewed clarity on why both types of work matter.

Culture Building and Founder Wellness.
Culture isn’t set by slogans but by the systems leaders build. One simple hiring ritual: in their first week, new employees make a list of people they’d love to work with again. Months later, if the hire is thriving, the company recruits from that list creating a self-reinforcing loop of cultural fit and talent quality. Another CEO shared personal habits for long term performance such as no drinking after difficult days, breathing practices to clear the mind before sleep, and approaching leadership with the same mental maintenance as elite athletes.

Mystery Shopping Your Own Company.
It’s easy for CEOs to assume they know what customers experience. One leader tested that assumption by going “incognito” and signing up for their own product under a personal email, recording every friction point, and comparing it to the company’s self-perception. The findings of confusing onboarding flows, missing follow-ups, small product glitches were eye-opening. The takeaway: firsthand experience is still the most powerful diagnostic tool in a CEO’s toolkit.

Rethinking One-on-Ones.
One company eliminated one-on-one meetings entirely. In their place: a daily 15-minute team huddle where everyone shares a win, a focus, and a challenge. The shift transformed information flows from siloed to collective. With fast-paced updates and live problem-solving, the company replaced “therapy sessions” with true alignment and reclaimed hours each week for deeper work.

Strategic Relationship Building.
Finally, several CEOs emphasized the compounding power of authentic relationships. The most valuable professional networks are built years before you need them by showing up, giving more than you take, and investing in peers who are also on the rise. Relationships built on genuine interest, not immediate agenda, often become the lifelines when opportunity or crisis arrives.

A Community of Builders

Our CEO Summit has always been about more than content, it’s about connection.

Across every conversation this year, one theme stood out: leadership is not a solo act. Whether it’s rebuilding a company you’re proud of or trading hard-won lessons with peers, progress comes from the willingness to share openly and learn together.

This year’s summit embodied what makes the Oregon venture community special: real conversations among peers who are building, learning, and leading together.

We left inspired and armed with a few new hacks of our own.