Head of Sales

Head Of Sales At 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.

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

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.

Must Have's

• Experience & Track Record

  • 10+ years of GTM experience, scaling revenue from ~$5–10M ARR to ~$50M+ ARR in a high-growth environment

  • Strong enterprise sales background with ability to operate across both Enterprise and Mid-Market

  • Demonstrated success with land-and-expand motions (ideally with strong NDR)

  • Experience in vertical SaaS preferred; otherwise strong track record selling to non-technical buyers

• Sales Motion & GTM Ownership

  • Deep understanding of enterprise (complex, relationship-driven) and mid-market (velocity, repeatability) sales motions

  • Owns both pipeline generation and closing, with experience leveraging SDRs, outbound, and events as core drivers

  • Ensure consistent top-of-funnel health alongside revenue targets

• Leadership Qualities

  • Strong aptitude for coaching Mid-market and Enterprise Reps to achieve/exceed quota

  • Past track record of 80-90% of team members hitting quota

  • Ability to attract and retain talent (strong ability to recruit top performers)

• Execution & Scaling

  • Operate with a quarterly planning mindset (pipeline, pacing, forecasting)

  • Experience in hyper-scaling environments (e.g., ~$4M → ~$16M → ~$40M ARR)

  • Able to build and scale early GTM systems, enablement and teams to support rapid growth

• Product Feedback Loop

  • Strong emphasis on capturing field learnings (customer conversations, objections, usage patterns)

  • Translates insights into clear product feedback, partnering closely with product/engineering to shape roadmap and improve win rates

• Working Style & Culture Fit

  • High-energy, hands-on builder willing to get in the trenches early

  • Comfortable operating with limited resources; not dependent on large teams to start

  • Strong communicator with tight feedback loops (e.g., highly responsive on Slack)

  • Ownership-driven, action-oriented, and excited by high-velocity, hyper-growth environments

  • Ability to work cross-functionally (product, CSMs, RevOps, etc.)

Nice to Haves

• Familiarity with hybrid pricing models (seat + consumption with upfront ARR)

• Experience in property & casualty insurance or adjacent industries

Key Success Metrics

• Net new annual recurring revenue (ARR)

• Net Revenue Retention (NRR)

• New logo + expansion pipeline created and closed

• Forecasting accuracy

Our Team and Philosophy

• Builders at heart. You don't wait for a process to exist—you create it, refine it, and own it.

• Bias toward action. You have an internal sense of urgency. You'd much rather get something done today than tomorrow.

• Owners, not renters. You treat the company's money and decisions like your own. You hold yourself accountable to outcomes, not just outputs.

• Ambitious about the opportunity. You're excited about building the defining AI company in the insurance industry—and you understand that great finance is a competitive advantage.

What We Offer

• Competitive salary + 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.