Scaling Agile: 20 to 80+ Builders
Agile Coach at Flywheel/WP Engine while the Scrum organization grew fourfold, from 20 builders to 80-plus. At Mutual of Omaha, trained client teams on Agile, Scrum, Kanban, and release planning.
Scaling the Organization
Over my four years at Flywheel the Scrum organization went from around 20 people running a handful of teams to more than 80 builders. Coaching it through that growth was the second half of my time there, after the product work. I ran the coaching, reshaped team structures as groups split, and built the cross-team coordination a group that size needs. I also coached leaders through the problems that come with fast growth.
Going from 20 to 80 usually costs a team its working conditions. Keeping that from happening was as much of the job as the structure. Teams kept the autonomy they had at 20, and the coordination we added on top was there to protect it rather than to police it.
Coaching the Coaches
The agile group itself was four people, and it reported to me. Coaching coaches turns out to be a different job from coaching teams, and most of it is deciding what to leave alone.
Each coach held their own teams and their own judgment about what those teams needed. My part was making the boundaries clear and then backing their calls in front of leadership when a team chose something unusual. A coach who gets overruled in public once stops making the call at all, and after that every decision comes back to me, which does not survive past a handful of teams.
Coaching & Frameworks
The framework varied by team: Scrum, Kanban, or SAFe, depending on what each one needed. Some thrived with strict two-week sprints. Others needed the flexibility of Kanban flow. At the portfolio level I introduced release planning and PI planning, which gave the whole organization visibility into what was coming and when.
Agile Outside Engineering
Marketing, customer experience, design, and product picked up the same practices. Engineering usually gets there first and then wonders why the rest of the company still works in quarterly batches.
Those groups needed a translation rather than a rollout. A marketing team running two-week iterations is not doing Scrum with different nouns, and pretending otherwise is how process earns a bad name. What carried over was the small parts: a visible backlog, a standing retrospective, and permission to stop something that was not working.
Training at Scale
At Mutual of Omaha, I trained thousands of clients on Agile, Scrum, Kanban, and release planning. These were hands-on workshops with practical tools teams could apply right away.
Certification & Growth
The Scrum certifications came from Jeff Sutherland, co-creator of Scrum, and Mike Cohn, one of the founders of the Scrum Alliance. They were a starting point. Most of the learning came from years of coaching teams through the reality of building software at scale.