A software giant getting its tentacles swimming in the same direction.

Problem

Paul Stovell built Octopus Deploy from a solo project into a global software company — 325,000+ users, 426 million deployments, and a team of 300+. But the growth pressures had fractured the executive team—who like the product, had grown one piece at a time.

Each leader ran their department well individually—with departments setting goals, cadences, and directions. But there was no cross-company framework for prioritising and planning, and leaders weren’t functioning as a team.

The bigger Octopus got, the harder it became to keep everyone swimming the same way.

Paul needed more than a coach. He needed someone who’d learn the business deeply enough to challenge the room, and who could then facilitate the hard conversations that weren’t happening on their own.

Solution

P7’s Anna Samios introduced the Scaling Up and Higher Playing FieldTM framework, starting with quarterly and annual strategic planning. She facilitated planning sessions that forced the owners and executive team to narrow down their long-term vision, set annual goals, and be accountable as one leadership group through quarterly rocks.

The shift was immediate. Leaders who’d previously only thought about their own teams started building the business around shared goals. Each member still led a department, but led together—in lockstep—with the rest of the executive team.

Anna had the experience—and thn took the time—to learn Octopus inside-out: the people, the dynamics, the quirks of each team. She became a sounding board for Paul on the things a CEO can’t always raise with their own team: the elephants in the room, the dynamics no one else could see.