Vice President of Sales, Flex
New Verticals
$400-500k
+ Company Equity
2-3 days a week in office
Flexible rent payment application
Open for applications
Flexible rent payment application
501-1000 employees
Open for applications
$400-500k
+ Company Equity
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
- The ideal candidate is a hands-on sales leader who has sold payment or fintech solutions into these verticals — not someone who has worked within them. You know the buyers, the conferences, the ecosystem, and you have a track record of closing first-of-kind deals
- 12+ years of experience in enterprise sales, strategic partnerships, or business development within FinTech or payments — with a demonstrated focus on new market entry
- Proven track record selling payment solutions into utilities, insurance, and/or broadband — not working within these industries, but selling to them
- Experience building and managing high-performing sales teams in a growth-stage or early-stage environment; you know how to hire, ramp, and develop sellers
- Deep understanding of the buyer landscape across target verticals: who the decision-makers are, how they evaluate vendors, and what drives urgency
- Demonstrated ability to close first-of-kind, complex enterprise deals involving novel product offerings and multi-party negotiations
- Strong financial and legal acumen — comfortable building deal models, structuring partnership economics, and negotiating contract terms
- Exceptional communication and executive presence; able to build trust with C-level stakeholders at prospective partner organizations
- Comfortable with ambiguity and rapid iteration — you build structure, don't wait for it
- High proficiency with Salesforce and data-driven sales methodologies; strong forecasting and pipeline management discipline
- Active presence at relevant industry conferences and associations is a strong signal of the right industry orientation
What the job involves
- As VP of Sales, New Verticals, you will own the strategy, execution, team, and revenue results for Flex's expansion into utilities, insurance, and broadband — three large, underserved markets where consumers deserve the same payment flexibility Flex pioneered in rent
- Reporting to the Head of Strategic Partnerships (New Verticals), you will build and lead a high-performing sales team from the ground up, define go-to-market strategy for each vertical, and personally drive the enterprise partnerships that will define Flex's next chapter. This is a zero-to-one opportunity: you'll be shaping market entry, not inheriting a playbook
- Strategy & Market Ownership
- Develop and own the go-to-market strategy for utilities, insurance, and broadband — defining ICP, target accounts, partnership models, and vertical-specific positioning
- Shape Flex's market entry approach in each vertical, translating market insight into executable sales plans with clear milestones and revenue targets
- Identify emerging trends, competitive dynamics, and new partnership opportunities to keep Flex ahead of the market
- Serve as the internal voice of each vertical — bringing customer and market feedback to Product, Marketing, and Leadership to influence roadmap and GTM strategy
- Team Building & Leadership
- Build and lead a high-performing vertical sales team — recruiting, onboarding, coaching, and retaining top talent across all three verticals
- Define team structure, roles, and coverage models as the business scales; grow headcount in line with pipeline opportunity and revenue performance
- Foster a culture of accountability, urgency, and collaboration; create an environment where reps are developed and top performers are retained
- Partner with HR and recruiting to identify and close exceptional sales talent with deep vertical expertise
- Pipeline & Revenue Execution
- Own and drive the full sales cycle for enterprise partnerships — from prospecting and qualification through negotiation, close, and launch
- Build and maintain a rigorous, data-driven pipeline; use CRM tools (Salesforce) to improve forecast accuracy, pipeline visibility, and deal velocity
- Lead complex, multi-stakeholder deal negotiations involving legal, economic, and technical terms within partnership agreements
- Personally carry and close strategic accounts while coaching the team to do the same at scale
- Cross-Functional Partnership
- Collaborate with Product and Engineering to ensure Flex's embedded payment offering is properly positioned and technically deployable within each vertical
- Partner with Marketing to develop vertical-specific content, campaigns, and event presence that supports pipeline generation
- Work with Partner Success to ensure seamless onboarding and long-term health of closed partnerships
- Represent Flex at key industry conferences (e.g., EUCI, Xchange, NAIC) to build brand visibility, source pipeline, and establish thought leadership
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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