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Senior Director, New Verticals Sales (Insurance)

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

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team?

About the Role

Flex is on a mission to give consumers control over their most significant recurring expenses — and auto insurance premiums sit squarely in that category. For most drivers, auto insurance is a non-negotiable monthly commitment, yet the payment experience has remained rigid and unforgiving. Flex changes that. As Director or Senior Director, New Vertical Sales (Auto Insurance), you will own Flex’s go-to-market strategy and commercial execution for the auto insurance vertical, building the enterprise partnerships that establish Flex as the embedded payment flexibility layer for carriers, agencies, and their policyholders.

Reporting to the VP of Strategic Partnerships (New Verticals), you will define the approach, build the pipeline, and close the deals that put this vertical on the map for Flex. This is a true zero-to-one charter — you will identify the right partners across personal lines carriers, independent agencies, and auto insurtechs, develop those relationships at the executive level, and drive deals from initial conversation through signed agreement and go-live. You will work hand-in-hand with Product, Engineering, Marketing, and Finance to shape Flex’s offering for the insurance market and ensure every partnership delivers real, measurable value.

This is a remote role is for an individual contributor who thrives in ambiguity, sets the agenda rather than waiting for one, and has the market credibility and executive presence to open doors and close deals in the auto insurance space. Success looks like a scaled, repeatable partner acquisition motion, a growing book of live carrier and agency partnerships, and a clear point of view on where Flex should go next in insurance.

What You'll Do

  • 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

Key Qualifications

  • 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

Compensation

Flex takes a market-based approach to pay, and compensation may vary depending on your primary work location. Work locations are categorized into one of three tiers based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be commensurate with their experience, qualifications, and Flex’s internal leveling guidelines and benchmarks. 

  • Senior Director, New Vertical Sales: $320,000-$400,000 OTE
  • Director, New Vertical Sales: $272,000 - $340,000 OTE

Life at Flex

We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace.

Offices

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.

Benefits

For full-time U.S. employees we offer:

  • 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

 For full-time non-U.S. employees, we offer:

  • Competitive compensation + company equity
  • Unlimited PTO

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