Mid-Market Account Executive

Mid-Market Account Executive

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.

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

You can clearly articulate Fulcrum's ICP, value prop, and competitive differentiation across buyer personas

You're consistently generating self-sourced pipeline and have active deals in motion

You've run full discovery-to-demo cycles and can clearly articulate what objections come up and how to handle them

You operate with high rigor: clean Salesforce notes, strong follow-up cadence, sharp prioritization

You've closed or are approaching close on your first deal

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

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

Builders  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.

Competitive salary + 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.