From the founders' circle to one leadership team

The situation

The company was a profitable Series C logistics SaaS business run by its co-founders, with about 400 people and a clear vision built on five big pillars. What it didn’t have was a way to turn that vision into shared decisions.

The co-founders made the big calls in informal meetings, without the rest of the leadership team. The wider leadership team heard about decisions rather than shaping them, and it showed in how engaged they were. A first try at OKRs (objectives and key results) had become a reporting nightmare, with a dozen team plans that didn’t line up. It made management more complicated instead of simpler.

The chief of staff brought me in to make OKRs work. It soon became clear the real question was how the leadership team worked together.

What we did

I started by listening. I interviewed the leadership team one by one, then ran a workshop where I showed them, in their own words, what was working and what was getting in the way across the team, the data, the strategy and how work got done.

The leaders chose two next steps. First, a weekly business review. I worked with their finance and revenue operations leads to build their own leadership metrics sheet, with weekly and monthly numbers on customers, revenue and churn, and we refined it over a few weeks.

Second, strategy and OKRs. Together we worked out where the company would play and how it would win, on one page. Then the whole leadership team came together in the room to turn the five pillars into company OKRs. We wrote the documents together, so they were the team’s own from the start.

The breakthrough

One priority was capacity: how many of its core transactions the product could handle. The plan was a big rebuild, about six months of work for a team of around 20 engineers.

In the OKR session, with the right people in the room and the focus on the result customers needed, the team saw they could raise capacity another way, using what they already had. That insight came straight out of the strategy and OKR discussion. The rebuild shrank to two months for three people.

What happened

The biggest change was in the leadership team itself. Decisions moved from the founders’ informal meetings into leadership team meetings, which built trust and improved alignment and engagement. Within three months they were running a weekly, monthly and quarterly rhythm, and they ran their own first two-day quarterly review across sales, product, engineering and customer teams. They shared their OKRs through the quarter, and the team broke through on five big priorities.

A few months later, the chief of staff looked back and said they had changed the whole way they work, in just three months.