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?
The Director of Sales will be responsible for leading and developing a high-performing sales team to achieve ambitious revenue targets and drive market share growth with a focus on enterprise-level clients and key accounts. This role requires a strategic leader with a proven track record in sales management, account planning, and team development. The Director of Sales will be instrumental in crafting and executing strategic account plans for our top key accounts, fostering a culture of continuous improvement through regular coaching, ensuring a robust sales pipeline, and ultimately delivering strong unit performance results.
What you’ll doSales Strategy & Planning
- Develop and execute a comprehensive sales strategy to drive revenue growth, expand market reach, and create strategic plans for key enterprise accounts.
- Analyze market trends, competitor activity, and customer needs to continuously refine sales tactics and strategy.
- Collaborate with Revenue Operations, Marketing, and Product teams to ensure alignment with overall business objectives.
- Represent Flex at industry events and conferences to enhance brand visibility and generate new opportunities.
Team Leadership & Development
- Recruit, build, and lead a high-performing enterprise sales team, providing ongoing coaching, mentorship, and performance management to foster a culture of excellence.
- Establish a results-driven team environment that encourages collaboration, accountability, and continuous learning.
Pipeline & Performance Management
- Oversee all aspects of the sales pipeline, from lead generation to deal closure, ensuring accurate forecasting and process efficiency.
- Monitor key sales metrics and performance indicators, driving the team to consistently meet and exceed revenue targets and quotas.
- Prepare and present regular sales performance reports, utilizing CRM data to deliver insights on progress, challenges, and market opportunities to senior leadership.
- 8+ years of experience in sales, with at least 4 years in a senior leadership role managing enterprise sales teams.
- A demonstrable track record of exceeding revenue targets in a competitive B2B environment, ideally within FinTech, PropTech, or SaaS industries.
- Proven success in developing and executing strategic account plans for large, complex, and key enterprise accounts.
- Extensive experience in recruiting, coaching, and developing a high-performing sales team focused on enterprise-level clients.
- Deep understanding of complex sales cycles and methodologies for navigating large organizations.
- Exceptional negotiation and communication skills, with experience presenting to and building relationships with C-level executives.
- Proficiency in using CRM software (e.g., Salesforce) for pipeline management, forecasting, and reporting.
- Strong analytical skills with the ability to use data to drive strategy and performance.
- Willingness and ability to travel frequently to meet with key clients and strategic partners.
The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks. This is a commission earning role. The OTE pay range will be $344,000-366,000.
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
Top Skills
What We Do
Flex, an NYC-headquartered FinTech company, has created a trusted rent payment experience. It’s hard to believe that it’s 2024 and paying rent on time is expensive, inflexible, and difficult; we’re here to change that! We enable our users to pay rent throughout the month on a schedule that better fits their finances and budget, while also helping them build credit.
Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense.
Why Work With Us
We believe it takes a diverse team of curious, determined, empathetic, and self aware people to grow a successful company. We value the unique and dynamic perspectives our team brings to solve critical problems that impact the lives of our users and the financial decisions they make.
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