[Remote] Senior Director, New Verticals Sales (Insurance)

Note: The job is a remote job and is open to candidates in USA. Flex is a growth-stage FinTech company headquartered in NYC that aims to revolutionize the rent payment experience. They are seeking a Senior Director for New Verticals Sales focused on auto insurance, responsible for developing and executing the go-to-market strategy and building enterprise partnerships.

Responsibilities

• Build Flex’s go-to-market strategy for the auto insurance vertical — identifying the highest-value partner segments across personal lines carriers, independent agencies, and insurtechs, and building the pipeline to pursue them
• 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, deeply understanding their strategic priorities and articulating exactly how Flex creates value for their policyholders and their business
• Close deals by owning complex, multi-stakeholder deal negotiations — structuring partnership economics that work for both parties while navigating legal, compliance, and procurement processes with urgency
• Shepherd each partnership from signed agreement through technical deployment and go-live, working closely with Product and Engineering to ensure strong execution and early performance metrics
• Translate partner feedback and competitive dynamics in the auto insurance market into actionable input for Product, Marketing, and Pricing — continuously sharpening Flex’s positioning and offering
• Build the auto insurance sales playbook — documenting learnings, establishing scalable processes, and developing the repeatable partner acquisition motion that enables efficient growth beyond initial market entry
• Leverage AI-assisted sales tools to drive pipeline efficiency, inform competitive strategy, and accelerate deal progression at scale

Skills

• 10+ years of experience in enterprise sales, business development, or strategic partnerships, with meaningful experience selling into or partnering with auto insurance carriers and independent agencies
• Deep knowledge of the auto insurance market — you understand how personal lines carriers and agencies operate, how premium payment and installment programs are structured, and where embedded payment flexibility creates value for policyholders and partners alike
• A track record of closing complex, first-of-kind enterprise deals in new markets, ideally involving embedded financial products, premium financing, or consumer payment programs in high-ACV, multi-stakeholder environments
• Executive presence and influence — you have operated confidently at the C-suite level, building trust with senior decision-makers at carriers and agencies and navigating complex organizations to drive deals to close
• Strong financial and legal acumen — you can build and defend deal models, structure partnership economics, and negotiate agreements with commercial rigor and an understanding of insurance regulatory considerations
• High agency and comfort with ambiguity — you define your own approach in undefined spaces, bring clarity and momentum to evolving situations, and set the agenda rather than waiting for direction
• Proven cross-functional leadership — you have aligned Product, Engineering, and Marketing around partner priorities and used those relationships to accelerate deal outcomes and improve the product
• Fluency with AI-assisted sales tools as a core part of your workflow — you use them to sharpen competitive intelligence, personalize outreach at scale, and drive more efficient pipeline management

Benefits

• 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
• Competitive compensation + company equity
• Unlimited PTO
• Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices.
• For candidates outside of these areas, you may be eligible for our relocation assistance program.

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