Head of Sales

Fulcrum•San Francisco, CA

19h•Onsite

About The Position

Fulcrum is building an AI platform to automate manual and repetitive insurance brokerage work. The company has achieved multiple seven figures in ARR in just over a year, serves large enterprise clients including 30% of the top 50 brokers in the country, and recently raised a Series A. The Head of Sales will build and lead Fulcrum’s revenue engine, taking the company from early traction toward category leadership. This role owns the full sales motion across Enterprise and Mid-Market, drives go-to-market strategy, and builds the GTM organization. The Head of Sales will hire and develop Account Executives and Business Development Representatives, lead pipeline generation and closing, and establish predictable revenue through disciplined forecasting, rigorous stage management, and close collaboration with Product. The role is a hands-on, ground-floor opportunity to shape how the insurance industry buys AI-powered software. Fulcrum describes its team as lean and staff-level, with in-person collaboration in San Francisco.

Requirements

10+ years of go-to-market experience, including scaling revenue from approximately $5–10M ARR to $50M+ ARR in a high-growth environment.
Strong enterprise sales background and ability to operate across Enterprise and Mid-Market.
Demonstrated success with land-and-expand sales motions, ideally with strong net revenue retention.
Deep understanding of complex, relationship-driven enterprise sales and repeatable, higher-velocity mid-market sales.
Experience owning pipeline generation and closing, including leveraging SDRs, outbound, and events.
Strong ability to coach Mid-Market and Enterprise sales representatives to achieve or exceed quota.
Track record of 80–90% of team members hitting quota.
Ability to recruit, attract, and retain top-performing talent.
Experience in hyper-scaling environments and building early GTM systems, enablement, and teams.
Ability to capture field learnings and translate them into clear product feedback in partnership with Product and Engineering.
High-energy, hands-on builder willing to work directly in early-stage sales execution.
Comfort operating with limited resources and without relying on large teams.
Strong communication skills and responsiveness, including through Slack.
Ownership-driven, action-oriented, and comfortable in a high-velocity, hyper-growth environment.
Ability to work cross-functionally with Product, Customer Success, and Revenue Operations.

Nice To Haves

Experience in vertical SaaS.
Experience selling to non-technical buyers.
Familiarity with hybrid pricing models combining seats and consumption with upfront ARR.
Experience in property and casualty insurance or adjacent industries.

Responsibilities

Build and lead the revenue engine and go-to-market organization across Enterprise and Mid-Market.
Own the full sales motion, including pipeline generation and closing.
Develop the go-to-market strategy.
Hire, coach, and develop a high-performing team of Account Executives and Business Development Representatives.
Use SDRs, outbound activity, and events as core pipeline-generation drivers.
Maintain top-of-funnel health alongside revenue targets.
Establish predictable revenue through quarterly planning, disciplined forecasting, and rigorous sales-stage management.
Build and scale early GTM systems, sales enablement, and teams to support rapid growth.
Capture customer conversations, objections, and usage patterns and translate those insights into product feedback.
Partner closely with Product and Engineering to shape the roadmap and improve win rates.
Work cross-functionally with Product, Customer Success, Revenue Operations, and other teams.
Drive performance against net new ARR, NRR, new-logo and expansion pipeline, and forecasting accuracy.