Mid-Market Account Executive

Fulcrum•San Francisco, CA

1d•$200,000 - $250,000•Onsite

About The Position

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. We're hiring a Mid-Market Account Executive to own a segment of the insurance brokerage market. You'll run a full sales cycle — from outbound prospecting through close — targeting mid-sized brokerages across the U.S. This is not a hand-off role. You'll source the majority of your own pipeline, run disciplined discovery, and close with urgency. You'll work directly with our founders and GTM leadership, and have meaningful input into how we build and scale our sales motion. If you're a sharp, hungry closer who wants to work on a product customers genuinely love — at a company with strong PMF and real momentum — this role is for you.

Requirements

5+ years of B2B closing experience with $50K+ ACV deals
Source most of your own pipeline — and treat outbound like a craft, not just volume
Write and speak with precision: your outreach gets replies, your demos move deals forward
Are energized by ambiguity, iteration, and building in a fast-moving environment
Are competitive and coachable — you take feedback and apply it immediately

Nice To Haves

Have sold into insurance, insurtech, financial services, or adjacent verticals
Have B2B SaaS or technical sales experience (e.g., Salesforce, Gong, Veeva)
Have worked at an early-stage startup or helped build a new sales motion from scratch
Have used Salesforce, Gong, Apollo, or similar GTM tools

Responsibilities

Own a mid-market territory end-to-end: prospecting, qualification, demo, negotiation, and close
Build self-sourced pipeline through cold outreach, sequencing, referrals, and industry events
Run structured discovery and tailored demos with Operations, IT, and C-suite stakeholders at mid-sized brokerages
Manage 30–50 active opportunities simultaneously with strong CRM hygiene and deal discipline
Collaborate with GTM and product teams to sharpen messaging, surface objections, and feed customer insight back into the roadmap
Contribute to the playbook — document what's working and help scale it across the team
Travel to industry events to represent Fulcrum and engage potential clients