Founding CSM

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 ($40B), 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.

This is a high-ownership, customer-facing role. You'll work directly with founders, and own how new customers experience Tailwind from the moment they sign through the point they're fully activated.

You'll be one of the faces of Tailwind through onboarding. You'll lead onboardings, building training, and defining what "activated" actually means for each customer. You'll also run the loop back into product, turning what customers are asking for into prioritized signal the team can act on.

We're looking for someone sharp, charismatic, and customer-obsessed- someone who can hold a room, write something a customer actually reads, and ship a v1 of the playbook this week instead of speccing the perfect one for a month.

• Own how new customers experience Tailwind from contract signature to full activation

• Build the onboarding playbook- kickoff materials, training, live sessions, in-app guides, and rebuild it as we learn what works

• Define what "activated" means for different customer types, measure it, and improve it over time

• Run the feedback loop back into product: capture what customers ask for, find the patterns, and partner with product to prioritize what ships next

• Be a force multiplier- every customer problem you solve should stay solved

• 2–4+ years in a customer-facing role at a B2B SaaS company (CSM, onboarding, implementation, solutions, training, devrel, etc.)

• You've built or meaningfully improved an onboarding or activation program — not just executed someone else's

• Strong written and verbal communication — charismatic on camera, sharp on the page

• Comfortable with ambiguity and energized by figuring things out as you go

• Experience collaborating with product and engineering to turn customer signal into shipped features

• Interest in AI and how it's reshaping modern workflows (hands-on experience is great, but not required)

We're building a company and a culture that prides itself on creating huge value for customers, and creating it quickly.

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 - people who know what great product looks like, and what it takes to build it fast.

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