Deployment Strategist

About Tailwind

Tailwind is organizing the world's insurance information.

Insurance is one of the largest markets in the world, and it runs entirely on PDFs and antiquated infrastructure. We like it that way. While the industry takes years to roll out change, we ship in days.

Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions.

About the Role

We’re a tight-knit team moving fast — the kind of place where you’ll work directly with leadership, wear many hats, and see your ideas in production fast.

As a Deployments Strategist you’ll work at our office in San Francisco and own the journey from “signed customer” to “activated teams of users.” You’ll design and execute onboarding plans, run kickoff and training sessions, and own the technical integration (mostly SQL). You may need to travel to customers from time-to-time ( A great candidate will be someone who loves creating order out of ambiguity and making customers feel like they’re in great hands.

What You’ll Do

Lead onboarding projects for new customers, ensuring timely and successful product adoption

Run engaging kickoff calls, training sessions, and Q&A meetings

Own technical integration for your customers (SQL, Cloud Platforms)

Identify opportunities to partner with customers to deliver new product or project based consulting engagements

Build and maintain onboarding materials: playbooks, quick start guides, how-to videos, and FAQs

Track progress against onboarding milestones and proactively address roadblocks

What Makes You a Great Fit

3–5 years of work experience in consulting, or in customer facing roles at a SaaS company

Experience juggling multiple deployments/projects at once

Exceptional written and verbal communication skills — you can make complex concepts easy to understand

Comfort operating in a fast-changing, resource-constrained startup environment

Empathy for customers combined with a bias toward action

Why You Should Work Here

Direct impact on customer satisfaction and retention

There are 2 ingredients to achieving high growth in your career; be great at your job, be a part of a fast growing company. We have one of those, the other is up to you.

Opportunity to see how the latest AI is being applied to solve high value problems

Our core team has worked together 3 times now, hailing from Carta ($7B) and AppDirect ($2B) and includes veterans from Ramp, Apple, Salesforce and C3 AI

Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions

We’re in-person at our beautiful offices 5 days per week in San Francisco (financial district). If you want to do the most meaningful work of your career, with an elite team, in a trillion dollar market, come join us!