Senior Director, New Verticals Sales – Insurance

Flex

Senior Director, New Verticals Sales focused on creating flexible payment solutions for auto insurance. Leading enterprise partnerships and sales strategies to grow Flex’s footprint in the insurance market.

Posted 5/4/2026full-timeNew York City • California, New York • 🇺🇸 United StatesSenior💰 $320,000 - $400,000 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
Serve as a credible, trusted advisor to C-level and senior decision-makers
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 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 as a core part of your workflow

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
Flex Cares Program: Non-profit company match + pet adoption coverage
Free Flex subscription

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

enterprise salesbusiness developmentstrategic partnershipsclosing complex dealsfinancial acumenlegal acumencross-functional leadershippipeline efficiency

Soft Skills

executive presenceinfluencecomfort with ambiguitytrusted advisor