Director of Sales Training & Enablement jobs in United States
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Flex ยท 2 days ago

Director of Sales Training & Enablement

Flex is a growth-stage FinTech company headquartered in NYC that aims to revolutionize the rent payment experience. They are seeking a Director of Sales Training & Enablement to build and scale their Revenue Enablement function, empowering global go-to-market teams to achieve their highest potential through strategic programs and data-driven insights.

AppsBillingFinancial ServicesFinTechSoftware

Responsibilities

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

Qualification

Revenue Enablement strategySales methodologiesAnalytical mindsetEnablement toolsPerformance data analysisTeam managementLeadership through influenceFacilitation skillsStorytelling skillsCommunication skills

Required

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

Benefits

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
Competitive compensation + company equity
Unlimited PTO

Company

Flex enables people to pay rent bills on a schedule that fits their personal finances.

Funding

Current Stage
Growth Stage
Total Funding
unknown
2025-03-31Series A
2019-11-01Seed
2019-07-24Pre Seed

Leadership Team

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Shragie Lichtenstein
Co-Founder & CEO
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Michael Jannain
Staff Software Engineer
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Company data provided by crunchbase