Director of New Vertical Sales, Flex
Auto Loans
$221-330k
OTE
Salary dependent on location. + Equity
Flexible rent payment application
Be an early applicant
Flexible rent payment application
501-1000 employees
Be an early applicant
$221-330k
OTE
Salary dependent on location. + Equity
501-1000 employees
Company mission
To help people pay for the things that matter most.
Role
Who you are
- 10+ years of experience in enterprise sales, business development, or strategic partnerships — with meaningful experience selling into or partnering with OEMs, dealership groups, auto lenders, auto insurtechs, or adjacent automotive platforms
- A track record of closing complex, first-of-kind deals in new markets, ideally involving embedded financial products, consumer payments, or BNPL programs in high-ACV, multi-stakeholder environments
- Deep knowledge of the auto ecosystem: You understand the dynamics between OEMs, dealers, lenders, and consumers — and you know how payment flexibility fits into the purchase and ownership lifecycle
- Executive presence and influence: You've operated confidently at the C-suite level, building trust with senior decision-makers and navigating complex organizations to drive deals to close
- Financial and legal acumen: You can build and defend deal models, structure partnership economics, and negotiate agreements — balancing commercial rigor with pragmatic deal-making
- High agency and comfort with ambiguity: You're energized by building in undefined spaces, don't wait for direction to take initiative, and bring clarity and momentum to evolving situations
- Cross-functional collaboration: You've successfully aligned Product, Engineering, and Marketing around partner priorities and used those relationships to accelerate deal outcomes
What the job involves
- 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 Senior Director, New Vertical Sales (Auto Loans), you will own Flex's go-to-market strategy and commercial execution for the auto loan vertical alternative finance companies
- Reporting to the VP of Strategic Partnerships, 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 deals 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
- Build and own Flex's go-to-market strategy for the auto loan vertical — identifying the highest-value partner segments
- Lead sales 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 borrowers and their business
- Close complex, multi-stakeholder deals — structuring partnership economics that work for both parties while navigating legal, compliance, and procurement processes with urgency and rigor
- 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 loan market into actionable input for Product, Marketing, and Pricing — continuously sharpening Flex's positioning and offering for the vertical
- Build and refine the auto loan 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, personalize outreach at scale, and accelerate deal progression — and set the standard for how the team uses AI to amplify sales impact
Our take
Many people struggle to pay their rent every month, with a variety of bills hitting their bank accounts simultaneously. Whilst many of these people earn enough money to cover their bills, the inflexible nature of monthly bills can make the all-in-one payment a harder obstacle.
Flex provides a mobile application for the flexible payment of rent, allowing users to pay their landlords through flexible payment plans, reschedule payments when necessary, and protect their funds through Overdraft Protection. The company achieves this by partnering with estate agents and paying their resident's bills upfront, taking on the challenges that landlords would normally have due to late payments.
Flex has experienced extremely rapid growth since its founding which has caused some issues, as it struggled to keep up with the surge in new customers. Having made improvements to its product and scaled its customer service team, it is set to continue providing a service that has come to be highly valued by both tenants and landlords.
Freddie
Company Specialist at Welcome to the Jungle
Insights
10% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Feb 2022
$160m
SERIES C
Apr 2021
$46.6m
SERIES B
Total funding: $225.1m
Company benefits
- Medical, Dental & Vision: Your healthcare will be available from Day 1— giving you immediate peace of mind — with best in class coverage and options.
- Parental Leave: Step away with paid time off to focus on family and life’s newest chapter.
- NYC HQ: Collaborate in our lively New York headquarters, with new office space on the way!
- 401(k) Retirement Savings: Plan ahead with our 401(k) program to grow your future. And starting early 2026, employees will be eligible for a company match!
- Flex Giving: Flex Giving empowers employees to support local nonprofits advancing housing stability in the communities we call home.
- Employee Assistance Fund: Confidential financial support to teammates facing unexpected hardships or emergencies.
- Hybrid Work Policy: Work flexibly from home, with in-person collaboration and events that matter.
- Unlimited PTO + Holidays: Take the time you need— whether that’s a vacation, recharge, or simply a long weekend
- Free Flex Subscription: As a Flex employee, you'll have full access to our services without charge.
- GrubHub Credit: Enjoy meal credits while in the office, so you’re fueled for the workday ahead.
Company HQ
Midtown Manhattan, New York, NY
Leadership
Shragie Lichtenstein
(Co-Founder & CEO)Prior to co-founding Flex in 2019, Shragie co-founded Boundless Reality. They graduated from Yeshiva University in 2015 with a Bachelor's Degree in Finance.
YeTong Shao
(Co-Founder)Prior to co-founding Flex in 2019, YeTong co-founded Boundless Reality alongside Shragie. They graduated from the University of Chicago with a Bachelor's Degree in Mathematic & Economics.
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