Last month, I completed an 8-week engagement as Head of Operations at Ciao Elsa, an AI-native startup. It was short, intense, and by design. Here's the full story — the good, the messy, and why walking away was the right call.
When Ciao Elsa reached out, they had a familiar problem: a great product, early traction, and operational chaos. Processes were ad-hoc. Decisions were made in Slack threads. The team was talented but spent more time firefighting than building.
The ask was clear: build an operations function from zero. Not a report. Not a recommendation. A functioning system that the team could run without me.
The first week was pure diagnosis. I mapped every process I could find — customer onboarding, support tickets, internal workflows, delivery cycles. The gaps were predictable: no clear ownership, no KPIs, no escalation paths. What surprised me was how hungry the team was for structure. They weren't resisting process — they were drowning without it.
By week 3, we had a framework. By week 5, the first dashboard was live. By week 7, the team was running the new processes autonomously. Week 8 was handover: documentation, training, success metrics.
So why leave?
Every engagement has a natural lifespan. This one was designed to be short from the start — build the system, prove it works, hand it over. The team at Ciao Elsa didn't need a permanent Head of Operations. They needed someone to build the runway so they could take off.
Not every engagement needs to be a multi-year commitment. Some of the most impactful work I've done happened in 8 weeks. The key is knowing when to build and when to hand over.
This experience confirmed two things for me: the operational playbook works at any stage — from enterprise to startup speed — and clean handovers are the ultimate sign of a job well done.