Director of New Verticals Sales, Flex
Auto Loans
$270-320k
OTE
2-3 days a week in office
Flexible rent payment application
Open for applications
Flexible rent payment application
501-1000 employees
Open for applications
$270-320k
OTE
2-3 days a week in office
501-1000 employees
Company mission
To help people pay for the things that matter most.
Role
Who you are
- We are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team?
- 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
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 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
- Build and own Flex's go-to-market strategy for the auto loan vertical — identifying the highest-value partner segments across captive and non-captive lenders, credit unions, and alternative finance companies, and building the pipeline to pursue them at scale
- Lead enterprise sales end-to-end, from prospecting and executive relationship-building through term sheet negotiation, contract execution, and go-live, while managing and developing a team of senior ICs
- 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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