Head of Sales

About Fulcrum

The $1.5 trillion insurance industry is powered by brokers. Every business needs insurance, and the brokerage industry is hamstrung by account management capacity. Account managers are constantly pulled in multiple directions—keying information into systems, chasing documents, doing mundane work—rather than focusing on the client interactions that actually matter. Most brokerages either outsource this work or grind through it manually.

We’re building an AI platform to automate this insurance drudgery. Our platform already saves customers thousands of hours and millions of dollars every year. Our customers love the product— we have deep penetration within enterprise brokerages and genuinely enjoy making our customers’ lives better. We just raised our Series A and are just getting started.

• Rocket-ship growth. We’ve achieved multiple seven figures in ARR in just over a year, serving large enterprise clients including 30% of the top 50 brokers in the country.
• Extreme ownership. You’ll work directly with enterprise users and ship end-to-end products that save them hours every week.
• Bleeding-edge problems, real impact. Tackle tough AI and product challenges whose wins show up immediately in customer workflows.
• In-person collaboration. Join a lean, staff-level team (ex-Affirm, Uber, Door Dash, McKinsey) working side-by-side in San Francisco; we believe the best ideas are fostered in an in-person environment.
• Top-of-market rewards. Competitive base salary plus meaningful founding-team equity.

As the Head of Sales at Fulcrum, you will build and lead the revenue engine that takes us from early traction to category leadership.

You’ll own the full sales motion end-to-end, across both Enterprise and Mid-Market, and build the GTM org that scales with it. You will drive the go-to-market strategy, hire and develop a high-performing team of AEs and BDRs, run the pipeline generation and closing motion, and make revenue predictable through disciplined forecasting, rigorous stage management, and a tight feedback loop with product.

This is a ground-floor opportunity, to architect how an entire industry buys AI-powered software.

• Experience & Track Record
• Sales Motion & GTM Ownership
• Leadership Qualities
• Execution & Scaling
• Product Feedback Loop
• Working Style & Culture Fit

• Familiarity with hybrid pricing models (seat + consumption with upfront ARR)
• Experience in property & casualty insurance or adjacent industries

• Net new annual recurring revenue (ARR)
• Net Revenue Retention (NRR)
• New logo + expansion pipeline created and closed
• Forecasting accuracy

• Competitive compensation ($400k-$600k OTE) + meaningful equity.
• Full health, dental & vision.
• High-ownership, high-trust culture with lightning-fast executors.
• Regular team off-sites, dinners, and an office stocked for builders.