Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team?
Reporting to the Head of GTM Operations & Strategy, this role will be responsible for the GTM strategy, operational support and execution of our front-line teams for the core part of our business. Flex GTM is one of the fastest-growing, high-performing, and mission-driven orgs in FinTech. We have driven 10x revenue growth every 2 years since inception and plan to do it again over the next 2 years. We are looking for a leader who can operationalize revenue initiatives and empower the front-line with world-class insights and process to 2x the growth of the core business year over year. We are looking for a driven and data-centric leader who is ruthlessly focused on practical implementation lead the strategy and operations team for this line of business.
This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters or 2 days per week in our San Francisco hub. For candidates outside of the NY/NJ/SF area, you may be eligible for our relocation assistance program.
What you’ll do- GTM Strategy & Annual Planning: Own annual and quarterly planning for the core business unit, and partner closely with Sales, Product and Analytics to develop and execute clear, data-driven go-to-market strategies
- Revenue Forecasting, Insights & Analytics: Own lead forecasting, pacing, and KPI reporting for the core GTM organization; Identify trends, risks, and opportunities across pipeline, funnel efficiency, and revenue performance
- Operational Excellence & Process Optimization: Develop and continuously refine sales processes, pipeline frameworks, sales territories and operating mechanisms to improve efficiency and consistency; partner with RevOps to ensure optimal execution within our Rev. systems environment
- Cross-Functional Leadership & Execution: Serve as the operational hub connecting Sales, Product, Marketing, Finance, Risk, and RevOps; bring structure and clarity to ambiguous problems; build repeatable systems from the ground up.
- Revenue Insights & Business Case Development: Conduct competitive analysis, market sizing, segmentation, and TAM analysis to inform GTM strategy; build business cases supporting new programs, product bets, investment decisions, and resource allocation.
- Lead the team: Develop and lead a revenue strategy and operations team of 3-4 in supporting the core business.
- 10+ years of experience in GTM strategy, revenue operations, strategy consulting, and/or business operations; 5+ years minimum experience in a revenue leadership role preferred
- Proven ability to lead strategic planning, forecasting, and operational programs in a high-growth B2B or multi-stakeholder environment.
- Deep analytical expertise to pull clear insights from complex data
- Strong understanding of sales processes, pipeline dynamics, and revenue forecasting best practices.
- Exceptional communication skills with the ability to influence executive stakeholders and cross-functional teams.
- Experience managing or leading complex cross-functional initiatives with significant business impact.
- Capable of operating both at a ‘30,000 foot’ strategic level, and getting into execution details, as the situation requires
- Experience in building processes and frameworks from the ground up.
- FinTech, marketplace, or network-based business experience is a strong plus.
Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines.
For candidates located in our Tier 1 markets (NYC/ SF), the base salary pay range for this role is $256,000 - $320,000. For all other U.S. locations, Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the Tier 1 states listed above, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location.
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.
We offer many employee benefits & perks. For full-time U.S based positions we offer:
- Competitive medical, dental, and vision available from Day 1
- Company equity
- 401(k) plan with company match (our company match kicks off at the beginning of 2026)
- Unlimited paid time off + 13 company paid holidays
- Parental leave
- Flex Cares Program
- Free Flex subscription
For full time non-US employees, we offer
- Competitive compensation + company equity
- Unlimited PTO
Flex Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Flex and has not been reviewed or approved by Flex.
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Healthcare Strength — Day-1 medical, dental, and vision coverage is explicitly offered and framed as “best-in-class coverage and options,” suggesting strong baseline health benefits. Additional listings also describe broad health-support elements such as IVF/adoption and gender transition benefits, reinforcing depth in healthcare-related coverage.
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Retirement Support — A 401(k) is available, with a stated company match starting in early 2026, indicating improving retirement support. This rollout appears to address earlier gaps where matching was not consistently present.
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Leave & Time Off Breadth — Unlimited PTO plus company holidays (and, in some descriptions, shutdown days) indicates a wide time-off policy on paper. Hybrid work flexibility and office-day meal credits can add to the overall rewards value for NYC-based employees.
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What We Do
Flex, an NYC-headquartered FinTech company, has created a trusted rent payment experience. It’s hard to believe that it’s 2024 and paying rent on time is expensive, inflexible, and difficult; we’re here to change that! We enable our users to pay rent throughout the month on a schedule that better fits their finances and budget, while also helping them build credit. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense.
Why Work With Us
We believe it takes a diverse team of curious, determined, empathetic, and self aware people to grow a successful company. We value the unique and dynamic perspectives our team brings to solve critical problems that impact the lives of our users and the financial decisions they make.
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