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 RoleAs a Sales Development Representative (SDR) focused on insurance brokers, you’ll own the very top of our sales funnel.
This is a great role for someone hungry to break into SaaS sales, learn the commercial insurance space, and grow into senior sales or go-to-market roles as Tailwind scales.
What You’ll DoResearch & prospect: Build targeted lists of insurance brokers using tools like LinkedIn Sales Navigator, and Apollo.
Outbound outreach: Run email, phone, and LinkedIn campaigns to engage brokers and book discovery calls.
Qualify leads: Quickly understand broker pain points and how Tailwind can help — then pass the most promising leads to the Sales team.
Collaborate with Sales & Marketing: Share broker feedback, refine messaging, and help shape our go-to-market motion.
Maintain pipeline hygiene: Track all activity and broker conversations in Salesforce.
Experiment & improve: Test new outreach sequences and messaging to drive higher connect rates with brokers.
1–4 years of experience in sales, recruiting, or other customer-facing roles (internships count).
Excellent communication skills — you can write clear, engaging outreach and handle phone conversations confidently.
Curiosity about financial services or interest in learning about insurance.
Persistence and resourcefulness — you’re comfortable doing research and trying new outreach tactics.
Experience with outreach tools (HubSpot, Apollo, Sales Navigator) a plus but not required.
Startup mindset: adaptable, fast-moving, eager to take ownership.
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.
Skills Required
- 1-4 years of experience in sales, recruiting, or other customer-facing roles
- Excellent communication skills
- Curiosity about financial services or interest in learning about insurance
- Persistence and resourcefulness
- Experience with outreach tools a plus but not required
What We Do
Tailwind powers stewardship reports for your entire book and new business. Top 100 brokerages across the US drive new business and deepen client relationships with trend analysis, loss summaries, ex mods, loss run retrieval, proposals, quote comparison, policy checking and more.
