Senior Director of New Vertical Sales, Flex
Mortgage
$310-390k
OTE
More information about location
2-3 days a week in office
Flexible rent payment application
Be an early applicant
Flexible rent payment application
501-1000 employees
Be an early applicant
$310-390k
OTE
More information about location
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
- You are the kind of person who brings energy into every room, pushes counterparts to think bigger, and finds a way to win even when the path isn’t clear
- 10+ years of experience in enterprise sales, business development, or strategic partnerships — with meaningful experience selling into or partnering with mortgage servicers, originators, LOS/servicing technology platforms, or adjacent fintech and proptech players
- 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
- We are seeking an entrepreneurial and highly accomplished Senior Director, New Vertical Sales to spearhead Flex’s expansion into the mortgage payment vertical
- The mortgage vertical represents one of the largest and most consequential recurring expense categories in American life — and one that has been dramatically underserved by modern payment flexibility solutions
- Reporting to the VP Strategic Partnerships (New Verticals), you will own Flex’s go-to-market strategy and pipeline for the mortgage vertical — identifying the right partners across mortgage servicers and servicing platform providers, and adjacent proptech players, and building the relationships and deals that establish Flex as the flexible payment solution for mortgage consumers
- You know the mortgage ecosystem from the inside — who the buyers are, how they think, and what it actually takes to get a partnership from whiteboard to go-live
- You’ll work hand-in-hand with Product, Engineering, Marketing, and Finance to shape our offering and ensure
- Build the Mortgage Vertical from the Ground Up: Identify, engage, and close enterprise partnerships across the mortgage ecosystem — including mortgage servicers, originators, and adjacent proptech and insurtech platforms — establishing Flex’s embedded split-pay offering as the standard for consumer payment flexibility in mortgage
- Develop and Manage a High-Value Pipeline: Build a disciplined, prioritized pipeline of strategic opportunities in the mortgage vertical, moving prospects through the sales cycle with urgency and converting them into live, revenue-generating partnerships
- Own Executive Relationships: Serve as a credible, trusted advisor to C-level leaders and senior decision-makers at target organizations — deeply understanding their strategic priorities and demonstrating exactly how Flex creates value for their customers and their business
- Lead Complex Deal Negotiations: Own term sheet and partnership agreement negotiations end-to-end, structuring deals that work economically and operationally for both parties while keeping momentum toward close
- Drive End-to-End Partnership Launch: Shepherd each partnership from signed agreement through technical deployment and go-live, working closely with Product and Engineering to ensure flawless execution and strong early performance metrics
- Influence GTM and Product Direction: Translate partner feedback and competitive dynamics in the mortgage market into actionable input for Product, Marketing, and Pricing — helping Flex continuously sharpen its positioning and offering for the vertical
- Build the Mortgage Playbook: Document learnings, establish scalable processes, and develop the repeatable partner acquisition motion that enables Flex to grow mortgage partnerships efficiently beyond initial market entry
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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