Senior Director, New Verticals Sales – Insurance

Flex

Senior Director leading go-to-market strategy for auto insurance at Flex. Engaging with enterprise partnerships and driving commercial execution across the insurance sector.

Posted 5/23/2026full-timeRemote • New York • 🇺🇸 United StatesSenior💰 $315,000 - $375,000 per yearWebsite

About the role

Key responsibilities & impact

Build Flex’s go-to-market strategy for the auto insurance vertical
Lead enterprise sales development end-to-end, from prospecting and executive relationship-building through term sheet negotiation, contract execution, and go-live
Serve as a credible, trusted advisor to C-level and senior decision-makers at target organizations
Close deals by owning complex, multi-stakeholder deal negotiations
Shepherd each partnership from signed agreement through technical deployment and go-live
Translate partner feedback and competitive dynamics in the auto insurance market into actionable input for Product, Marketing, and Pricing
Build the auto insurance sales playbook
Leverage AI-assisted sales tools to drive pipeline efficiency

Requirements

What you’ll need

10+ years of experience in enterprise sales, business development, or strategic partnerships
Deep knowledge of the auto insurance market
A track record of closing complex, first-of-kind enterprise deals in new markets
Executive presence and influence
Strong financial and legal acumen
High agency and comfort with ambiguity
Proven cross-functional leadership
Fluency with AI-assisted sales tools

Benefits

Comp & perks

Competitive medical, dental, and vision
Company equity
401(k) plan with company match
Unlimited paid time off + 13 company paid holidays
Parental leave
Free Flex subscription

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

enterprise salesbusiness developmentstrategic partnershipsdeal negotiationcontract executionpipeline efficiencyfinancial acumenlegal acumencross-functional leadershipgo-to-market strategy

Soft Skills

executive presenceinfluencecomfort with ambiguitytrusted advisorrelationship-buildingactionable feedback translationleadershipnegotiation skillscommunicationproblem-solving