Director of Sales Training & Enablement

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

We’re looking for a strategic, collaborative, and data-driven leader to build and scale our Revenue Enablement function. As the Director of Revenue Enablement, you’ll be responsible for empowering our global go-to-market (GTM) teams, including Sales across multiple industry verticals, Partner Success, and Business Development, to perform at their highest potential. This role sits at the intersection of strategy, learning, and operations, ensuring our teams have the knowledge, tools, and confidence to deliver consistent, high-impact experiences for our partners. You’ll design programs that align with business goals, drive measurable outcomes, and foster a culture of continuous improvement and shared success.

This role reports to the VP GTM Strategy & Operations and works in close partnership with leaders across Revenue, Marketing, and Product.

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 SF hub. For candidates outside of the NY/NJ/SF area, you may be eligible for our relocation assistance program.

What you’ll do

• Define and execute the Revenue Enablement strategy aligned to business goals, sales objectives, and customer outcomes, balancing long-term vision with agile delivery.

• Partner across the Revenue organization to identify performance gaps, prioritize needs, and design programs that improve efficiency, conversion, and customer satisfaction.

• Build scalable enablement programs covering onboarding, continuous learning, sales methodologies, product readiness, and leadership development for client-facing managers.

• Leverage data and analytics to measure impact, connecting enablement efforts directly to business KPIs such as ramp time, win rate, and retention.

• Coach and develop a high-performing enablement team, providing clarity, mentorship, and accountability to ensure excellence across projects and initiatives.

• Champion technology adoption, ensuring our enablement stack (CRM and other sales/lead tools, content management, conversational intelligence, LMS) is fully utilized to drive productivity and insight.

• Facilitate cross-functional alignment, ensuring consistent messaging, efficient GTM execution, and readiness across all customer touchpoints.

Key qualifications

• 8+ years of progressive experience in Revenue, Sales, or GTM Enablement, with at least 3+ years in a leadership role (team management and strategic program ownership).

• Proven success building, scaling, and measuring enablement programs in a high-growth environment.

• Deep understanding of modern sales methodologies and the end-to-end customer journey.

• Strong analytical and operational mindset, able to interpret performance data, generate insights, and translate them into action.

• Expert-level knowledge of enablement and Revenue tools (Salesforce, HubSpot, Gong, etc.).

• Exceptional facilitation, storytelling, and communication skills; able to engage executive audiences and front-line teams alike.

• Demonstrated ability to lead through influence, partnering across functions to align on goals, resolve challenges, and drive execution.

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, the base salary pay range will be $211,000 - $226,000.

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 & 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