Head of Sales

FulcrumSan Francisco, CA
10h$400,000 - $600,000Onsite

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)
  • 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
  • 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)
  • 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
  • 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
  • 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

Benefits

  • 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.
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