Board of Directors at an AI Company
Board Management at Conversica (The Wins)
When I joined Conversica in late 2019, I inherited a board with diverse viewpoints, investor interests, and historical inertia. My goal was simple—but far from easy: evolve the board from a governance body into a strategic asset.
We went from standard board reporting to strategic integration—with board members attending my QBRs, reviewing KPI dashboards in monthly business reviews, and participating in board-led strategy workshops (where board members presented to the broader team on topics they were capable of being the teacher versus the student). This wasn’t just window dressing—it was about building fluency, trust, and shared accountability.
By 2023, certain directors became extensions of the leadership team—coaching execs, mentoring rising leaders, and even facilitating working sessions during offsites. We weren’t just presenting PowerPoints; we were co-architecting strategy.
Ideally, use the boardroom to test product-market theses before taking them to market. Board members aren’t just advisors—they become pressure testers, accelerators, and at times, amplifiers of our vision.
Board Management – Strategic Headwinds (The Losses)
But not all progress was linear.
The same diversity that added resilience also created friction. We were often caught between visionary ambition and fiduciary caution. In moments that demanded bold bets—whether a transformative M&A, GTM overhaul, or product pivot—the board defaulted to safety.
Our boldest ideas often died in the shadows of indecision.
Some board members weren’t calibrated for the velocity or volatility of building in a GenAI era. Others misunderstood their role—not as protectors of the cap table, but as stewards of outsized impact.
When I needed consensus, I got committee. When I needed a spark, I got a spreadsheet. We didn’t lack smart people—we lacked aligned courage.
Advice From One CEO to Another – Building a High-Impact Board
- Set Cultural Expectations Early
Make clear whether your board is a cockpit or a control tower. You can’t build a rocket with commercial airline protocols. - Avoid the Hero-Villain Trap
It’s not about good or bad board members. It’s about the right fit for your company’s phase and ambition. - Assign Homework
Equip board members with roles—mentor, challenger, sponsor. Passive governance invites passive outcomes. - Teach Strategy, Not Just Tactics
Hold quarterly workshops where they teach the team. Flip the script. Great leaders make great learners. - Celebrate Decision-Making Velocity
Governance shouldn’t be a bottleneck. Create a shared cadence for bold, timely decisions—even if imperfect. - Measure Their Impact Like Any Other Exec
Scorecards aren’t just for C-levels. Measure board contributions to talent, capital, customers, and vision.
Conclusion
Board management at Conversica was a tale of two paths: one paved by intentional integration, the other stalled by cautious governance. We didn’t always get the board we needed—but we worked to shape the one we had.
For future CEOs: don’t settle for governance. Build a board that governs and galvanizes.
“The best boards don’t steer from the shore—they climb aboard, row hard, and aren’t afraid to change course when the storm hits.”
