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About the Role
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.
Responsibilities
- Own the full sales motion end-to-end, across both Enterprise and Mid-Market
- Build the GTM org that scales with the company
- Drive the go-to-market strategy
- Hire and develop a high-performing team of AEs and BDRs
- Run the pipeline generation and closing motion
- Make revenue predictable through disciplined forecasting, rigorous stage management, and a tight feedback loop with product
- Capture field learnings (customer conversations, objections, usage patterns)
- Translate insights into clear product feedback, partnering closely with product/engineering to shape roadmap and improve win rates
- Coach Mid-market and Enterprise Reps to achieve/exceed quota
- Attract and retain talent
- Operate with a quarterly planning mindset (pipeline, pacing, forecasting)
- Build and scale early GTM systems, enablement and teams to support rapid growth
Requirements
- 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
- 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
- Past track record of 80-90% of team members hitting quota
- Experience in hyper-scaling environments (e.g., ~$4M → ~$16M → ~$40M ARR)
- 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
- Ownership-driven, action-oriented, and excited by high-velocity, hyper-growth environments
- Ability to work cross-functionally (product, CSMs, RevOps, etc.)
- Familiarity with hybrid pricing models (seat + consumption with upfront ARR)
- Experience in property & casualty insurance or adjacent industries
Skills
- Sales
- Go-to-Market Strategy
- Revenue Growth
- Enterprise Sales
- Mid-Market Sales
- Land-and-Expand
- Vertical SaaS
- Pipeline Generation
- Closing
- Forecasting
- Coaching
- Talent Acquisition
- Team Building
- System Scaling
- Product Feedback
- Cross-functional Collaboration
- Communication
Location
- San Francisco
Work Type
- In-person collaboration
- Full-time
Experience Level
- 10+ years of GTM experience
- Founding-team level
Salary/Compensations
- Competitive salary
Benefits
- Meaningful founding-team equity
- Full health, dental & vision
- High-ownership, high-trust culture
- Regular team off-sites, dinners
- Office stocked for builders
About the Company
- The $1.5 trillion insurance industry is powered by brokers.
- 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.
- 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.
- 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, DoorDash, 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.
- 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.