Mid-Market Account Executive

About this role

Mid-Market Account Executive

Work type: Full time · Department: Sales · Workplace: On-Site

New York, United States (Remote); San Francisco, California, United States

About Fulcrum

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.

Why Fulcrum

• 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.

About the Role

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.

What You'll Do

• 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

What Success Looks Like (First 90 Days)

• 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

You Might Be a Fit If You

• 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

Bonus Points if You

• 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

What we offer

• Competitive salary ($200k-$250k 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.