Acting CTO for a healthtech founder between hires

Sarah had built the company from a clinical insight nobody else had spotted. Now she was sitting across from a HIPAA auditor explaining authentication flows she didn't fully understand, watching her lead engineer try to translate her words back into sentences that wouldn't fail the audit.

Every major decision was bottlenecked on her — and she knew she was the wrong person to be making half of them. Vendor contracts she couldn't evaluate. Architecture choices she had to take on faith. Hiring loops where she couldn't tell a strong senior engineer from a confident one. The board kept asking 'when's the CTO hire?' and she kept saying 'soon' because the honest answer — 'I don't know how to interview for that' — felt unsayable.

In our first session, we didn't open a Notion doc or a roadmap template. We made a list of every technical decision Sarah had postponed in the last 60 days because she didn't trust her own judgment on it. There were 23 items. Within four weeks, we'd worked through them together — and she stopped flinching when investors asked technical questions.

• Weekly office hours with the founder and lead engineer — same time, same room, every week
• Architecture review on every major technical decision before commitment
• Designed and ran the senior engineer hiring loop end-to-end
• Owned the technology narrative for the Series A deck and DD process

Closed Series A with a clean technical DD, hired two senior engineers and a lead, and handed off to a permanent CTO at month nine with full context — including a written briefing on every major decision the company had made in the previous year.