A remote Engineering Leadership role at Flex.
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Flex is on a mission to give consumers control over their most significant recurring expenses — and auto loans represent one of the largest, most underserved opportunities to do exactly that. Auto loan payments are a defining financial commitment for millions of Americans, yet the flexibility and control consumers expect from modern financial products has largely passed this category by. As the Director or Senior Director, New Vertical Sales (Auto Loans), you will own Flex's go-to-market strategy and commercial execution for the auto loan vertical, building the enterprise partnerships that establish Flex as the embedded payment flexibility layer for captive and non-captive lenders, credit unions, and alternative finance companies.
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 the auto finance ecosystem, 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 auto loan market and ensure every partnership delivers real, measurable value for Flex's partners and their borrowers.
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 finance space. Success looks like a scaled, repeatable partner acquisition motion, a growing book of live lender partnerships, a high-performing team behind you, and a clear point of view on where Flex should go next in auto lending.
10+ years of experience in enterprise sales, business development, or strategic partnerships, with meaningful experience selling into or partnering with auto lenders, credit unions, or alternative finance companies
Deep knowledge of the auto finance ecosystem — you understand how captive and non-captive lenders, credit unions, and alternative finance companies operate, how loan servicing and payment programs are structured, and where embedded payment flexibility creates value for borrowers and lenders alike
A track record of closing complex, first-of-kind enterprise deals in new or emerging markets, ideally involving embedded financial products, consumer payments, or BNPL 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 and navigating complex organizations to drive deals to close
Proven experience leading, developing, and scaling a high-performing enterprise sales team, including setting KPIs, coaching senior ICs, and driving accountability against ambitious targets
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 consumer lending 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
Fluency with AI-assisted sales tools as a core part of your workflow — you use them to sharpen competitive intelligence, personalize outreach at scale, drive more efficient pipeline management, and model best practices for your team
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.
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.
Flex
YC S23Engineering Leadership
4 open roles on Sydicom
Flex is a payment platform for businesses to accept HSA/FSA, unlocking the $150B per year sitting in HSA/FSA accounts.
Source: Y Combinator
