Director of Sales Training & Enablement, Flex
$211-226k
+ Company equity
More information about location
3+ days a week in office
Flexible rent payment application
Open for applications
Flexible rent payment application
501-1000 employees
Open for applications
$211-226k
+ Company equity
More information about location
3+ days a week in office
501-1000 employees
Company mission
Flex's mission is to empower as many renters as possible with flexibility over their most significant recurring expense.
Role
Who you are
- We’re looking for a strategic, collaborative, and data-driven leader to build and scale our Revenue Enablement function
- 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
What the job involves
- 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
- 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
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
- 100% company-paid medical, dental, and vision
- 401(k) + company stock options
- Unlimited paid time off + company paid holidays
- Parental leave + IVF and adoption support
- Flex Cares Program: Non-profit company match + pet adoption coverage
- Pet Insurance
- Free Flex subscription
Company HQ
Midtown Manhattan, New York, NY
Leadership
Shragie Lichtenstein
(Co-Founder & CEO)Experience working in venture capital investments for Point72 and TVC. Also co-founded Boundless Reality.
YeTong Shao
(Co-Founder)Experience as Data Science Researcher. Also co-founded Boundless Reality.
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