Account Executive

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.

As an Account Executive at Tailwind, you’ll own the entire sales cycle for insurance brokers — from the first discovery call to close. You’ll help producers and account managers modernize their workflows with Tailwind, driving adoption and shaping how commercial insurance gets done.

This is a role for someone hungry to close deals, build relationships, and grow into a senior sales or go-to-market leader as Tailwind scales.

• Own the full sales cycle: Manage broker leads from discovery to close.

• Run high-impact demos: Clearly communicate Tailwind’s value to brokers at different levels of complexity.

• Forecast & manage pipeline: Keep deals moving through the funnel, with accurate forecasts in Salesforce.

• Collaborate cross-functionally: Work with Product, Marketing, and Customer Success to share broker feedback and shape messaging.

• Hit & exceed quota: Consistently close deals and help us build repeatable sales motion.

• Experiment & iterate: Test new messaging and outreach sequences to shorten the sales cycle.

• 2–6+ years of closing experience in B2B SaaS (ideally mid-market+).

• 1-2 years in sales development.

• Strong communicator — you can build rapport quickly and run consultative sales calls with confidence.

• Organized & process-oriented — you manage pipeline rigorously and forecast accurately.

• Interest in financial services and insurance is a plus.

• Startup mindset: adaptable, resourceful, comfortable building processes from scratch.

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.

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) - 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.