Head of Sales

Fulcrum•San Francisco, CA

2d•Onsite

About The Position

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.

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

Experience in vertical SaaS preferred; otherwise strong track record selling to non-technical buyers
Familiarity with hybrid pricing models (seat + consumption with upfront ARR)
Experience in property & casualty insurance or adjacent industries

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
Own both pipeline generation and closing, with experience leveraging SDRs, outbound, and events as core drivers
Ensure consistent top-of-funnel health alongside revenue targets
Operate with a quarterly planning mindset (pipeline, pacing, forecasting)
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