Senior Director of GTM Strategy & Operations, Flex
$265-315k
+ Equity
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
$265-315k
+ 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
- 10+ years of experience in GTM strategy, revenue operations, strategy consulting, and/or business operations preferred; 5+ years minimum experience in a revenue leadership role
- Proven ability to build GTM strategy and operational infrastructure in a greenfield or early-stage business context — not just optimizing what exists, but creating from scratch
- Strong analytical expertise with the ability to pull clear, actionable insights from incomplete or early-stage data
- Deep understanding of sales processes, pipeline dynamics, and revenue forecasting best practices, with the ability to adapt frameworks across different business models and buyer types
- Exceptional communication skills with the ability to influence executive stakeholders and cross-functional teams across multiple business lines simultaneously
- Comfortable operating in ambiguity — able to make good decisions with limited information and build structure around unstructured problems
- Capable of operating at both a strategic and execution level as the situation demands; willing to roll up sleeves in an early-stage environment
- Experience building processes and frameworks from the ground up
- FinTech, marketplace, or network-based business experience is a strong plus; experience operating across multiple business lines or verticals simultaneously is equally valued
What the job involves
- 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 across Flex's New Verticals business. As Flex expands beyond its core market into new segments, this leader will play a foundational role in building the GTM infrastructure that enables us to scale
- We are looking for a builder — someone who thrives in ambiguity, moves quickly to structure the unstructured, and brings both strategic rigor and operational horsepower to a business that is early but moving fast. This is a high-visibility role that will directly shape how new lines of business grow, and will require close partnership with Sales, Product, Analytics, Finance, and the broader GTM leadership team
- GTM Strategy & Annual Planning: Own annual and quarterly planning for the New Verticals business unit, partnering closely with Sales, Product, and Analytics to develop and execute clear, data-driven go-to-market strategies tailored to each vertical's unique dynamics
- Revenue Forecasting, Insights & Analytics: Own lead forecasting, pacing, and KPI reporting for the New Verticals GTM organization; identify trends, risks, and opportunities across pipeline, funnel efficiency, and revenue performance; build the reporting infrastructure largely from scratch as new verticals mature
- Operational Excellence & Process Optimization: Design and continuously refine sales processes, pipeline frameworks, territory structures, and operating mechanisms purpose-built for new verticals; partner with RevOps to ensure optimal execution within Flex's revenue systems environment
- Cross-Functional Leadership & Execution: Serve as the operational hub connecting Sales, Product, Marketing, Finance, Risk, and RevOps across the New Verticals portfolio; bring structure and clarity to ambiguous, fast-moving problems; build repeatable systems that can scale with the business
- Revenue Insights & Business Case Development: Conduct market sizing, segmentation, and TAM analysis for new verticals; build business cases supporting go/no-go decisions, new programs, product investments, and resource allocation across the portfolio
- Lead the Team: Develop and lead a revenue strategy and operations team supporting the New Verticals business, with expectation to grow the function as the verticals scale
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.
Salary benchmarks
We don't have enough data yet to provide salary benchmarks for this role.
Submit your salary to help other candidates with crowdsourced salary estimates.
Share this job
View 33 more jobs at Flex