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About the Role

We are hiring a Mid-Market Account Executive to own a segment of the insurance brokerage market. You will run a full sales cycle, from outbound prospecting through close, targeting mid-sized brokerages across the U.S. This role requires sourcing the majority of your own pipeline, running disciplined discovery, and closing with urgency. You will work directly with founders and GTM leadership, influencing how we build and scale our sales motion.

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

Requirements

Have 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

Skills

Salesforce
Gong
Apollo

Location

San Francisco

Work Type

In-person collaboration
Full-time

Experience Level

Mid-Market
5+ years of B2B closing experience

Salary/Compensations

Competitive base 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.
We're building an AI platform to automate insurance drudgery.
Our platform already saves customers thousands of hours and millions of dollars every year.
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.