Deployment Strategist

We are looking for a Deployment Strategist with 4–8 years of experience to own the post-sale journey from contract signature to full customer activation at Tailwind. You'll be the face of implementation for enterprise insurance brokerages — part project manager, part technical integrator, part relationship builder — and you'll help design the very program you're executing. This is a founding hire in this function, so there's real ownership and room to grow.

What will you be doing?

- Own onboarding end-to-end for enterprise accounts — from kickoff calls and training sessions to full user activation

- Build and iterate on the onboarding program itself: playbooks, activation metrics, milestone tracking, and change management frameworks

- Handle technical integrations independently (SQL, cloud platforms) without needing engineering support

- Serve as the primary relationship owner for customers post-sale, ensuring they feel confident, supported, and fully adopted

- Feed product insights back into the development cycle based on what you're seeing in the field

Key Requirements

- Technical background is non-negotiable — must be comfortable with SQL and have strong product intuition; candidates who can't do technical integration work won't pass the interview

- Executive presence and strong interpersonal skills — you'll be managing relationships with senior stakeholders at large brokerages who need to feel confident in you

- Experience building or contributing to an onboarding/deployment program, not just executing one — founding-hire or early-stage startup experience is a strong signal

- Background in Technical Account Management, Program Management, or a similarly hybrid technical + client-facing role

- Based in San Francisco and able to work in-person 5 days/week in the Financial District