VP of GTM Strategy & Operations

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 2025 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?

About the role

Reporting directly to our Revenue Leader, the Head of GTM Operations & Strategy will be responsible for supporting the buildout and leadership of our world-class GTM org. 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 enhance and scale our revenue growth function as we take on new strategic business opportunities spanning new market exploration, new product expansion, new partner channels, and many other revenue-enhancing initiatives. We are looking for a driven, passionate, and data-centric leader to own GTM Operations and the functions that support it: Revenue Operations, Enablement, Partner Marketing and Implementation.

What you’ll do

• Go-To-Market Growth Strategy: Own and execute a holistic, verticalized GTM strategy, inbound/outbound demand generation, and sales channels/motions in a multi-segment model that consists of a combination of enterprise/mid-market/smb and direct/indirect revenue
• TAM Expansion: Drive identification of new distribution channels & markets, build the business case for resourcing, and lead execution from proof of concept to scalable motion
• Strategic Alignment: Translate company-wide and go-to-market objectives into actionable and impactful revenue operations initiatives
• Sales Effectiveness: Provide direct leadership to our Revenue Operations, Enablement Partner Marketing and Implementation teams, ensuring tight alignment with Flex GTM priorities
• Revenue Operations: Manage the day-to-day operational needs of the Core Sales & Post-sales teams, including TAM, Territory/Comp, CRM, and other supporting systems
• Revenue Optimization: Continuously assess and improve processes, tools, and methodologies to increase sales growth velocity
• Strategic Insights: Leverage HubSpot, Sigma, Excel, and other advanced business intelligence tools to provide insights, forecast trends, and drive decision-making
• Talent Development: Attract and develop an A+ team, spanning Revenue Operations, Enablement, Implementation, and Partner Marketing
• Stakeholder Management: Ensure visibility into priorities and progress for key GTM and cross-departmental leaders and collaborators, keeping GTM in sync with the larger business

Key qualifications

• Minimum 8 years’ experience in revenue and or business operations leadership roles; 10+ years preferred
• Proven experience leading GTM & revenue operations functions in a hyper-growth company with $150M+ in revenue
• Experience supporting B2B sales orgs of 75+ HC in a high-velocity, verticalized GTM Motion
• Track record selling up and down market (SMB to Enterprise), leveraging inbound and outbound Lead Gen motions
• Experience evolving and expanding GTM processes/playbooks to support new product expansion and high-velocity cross-sell
• Proven ability to collaborate with and ideally lead supporting functions (e.g., Partner Marketing, Implementation) to further accelerate growth
• Adept with business intelligence tools; can quickly isolate the “so what” for the business and push evolution of processes and tooling to track it
• Strong analytical, strategic thinking, and problem-solving skills
• Exceptional interpersonal and communication skills
• Ability to work collaboratively across teams and departments
• Prefer to tackle problems from first principles
• Bachelor's degree in Business, Marketing, or a related field. Master's degree a plus

The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks. For working locations in NY/NJ/CA, the base salary pay range will be $278,000 - $295,000.

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. For full time, U.S. based employees we offer:

• Competitive pay
• 100% company-paid medical, dental, and vision
• 401(k) + company equity
• Unlimited paid time off with a PTO minimum + 13 company paid holidays
• Parental leave
• Flex Cares Program: Non-profit company match + pet adoption coverage
• Free Flex subscription

For full time non-US employees, we offer

• Competitive Pay
• Company Equity
• Unlimited PTO