Director of Enterprise Sales

The Role

We're hiring a Director, Enterprise Sales, reporting directly to the Head of GTM. You'll lead a team of enterprise AEs selling multi-year platform deals into carriers, brokers, and MGAs, and you'll own the team's number. As the Director, Enterprise Sales you will be key in scaling our GTM function, driving revenue growth, and ensuring the team's success.

This is a management role. You won't carry an individual quota. Your leverage is who you hire, how well you coach them, and how tightly you run the process.

In-person, New York.

What You'll Do

Build and Lead the Team

• Hire, ramp, and develop enterprise AEs, and raise the bar with every hire
• Coach on qualification, multi-threading, and executive presence
• Set a high-performance culture with clear expectations and fast feedback

Own the Number

• Own forecast accuracy and pipeline health for the enterprise segment
• Run weekly forecast, pipeline review, and deal inspection with the Head of Sales
• Diagnose funnel leakage and fix it at the source: sourcing, qualification, or close

Drive the Biggest Deals

• Act as executive sponsor on our largest opportunities, open doors, hold senior relationships at COO, Chief Claims Officer, and CIO level, and put your AEs in front of them
• Keep your team and the applied AI team aligned on POV scoping, technical evaluations, and conversion to production
• Unblock enterprise procurement, security review, and legal so deals close on time

Build the Motion

• Assist in territory design, account segmentation, and quota allocation for the segment
• Turn what wins into playbooks: discovery frameworks, POV structure, competitive positioning against BPOs and legacy insuretech
• Feed the field's signal back into product, pricing, and marketing

What We're Looking for

• 4+ years leading quota-carrying enterprise AEs, with a track record of exceeding team target
• 8+ years in a quota-carrying role
• Experience leading teams through six- and seven-figure deals with long, multi-stakeholder procurement cycles
• Trained in MEDDPICC or a comparable value-selling framework, and experienced installing it across a team without turning it into paperwork
• Comfortable in a technical sale: you can hold your own on how the product actually works and what it will and won't do
• Early-stage experience where you built the process rather than inherited it
• You measure yourself by how much better your reps get, not by the deals you personally touch
• Clear, precise communicator who can translate complexity into decisions
• Comfortable with the unglamorous parts of management: performance conversations early, comp and quota discussions, and hiring fast without lowering the bar

Nice to Have

• Insurance experience: P&C, specialty, life, MGAs, or brokers
• Experience displacing incumbent BPO or offshore services spend
• Sold AI or automation products where the buyer is an operations leader, not IT
• Fluency with Salesforce and revenue intelligence tooling

Compensation & Benefits

• Competitive base + variable, with meaningful early-stage equity
• Full medical, dental, and vision coverage
• Unlimited PTO
• In-person, New York City