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.

About the role

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 do

Sales 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.
• 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.

Key Qualifications

• 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.

We offer many employee benefits, including competitive pay, 100% company-paid medical, dental, and vision, 401(k) + company equity, unlimited paid time off + 13 company paid holidays, parental leave, Flex Cares Program, and free Flex subscription.

Flex is an equal opportunity workplace. We do not discriminate on the basis of any protected group status under any applicable law.