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VP of Sales

New York, New York, United States

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

As the Vice President of Sales, you will be responsible for building and executing a high-impact sales strategy that drives revenue growth, market expansion, and enterprise adoption of Flex’s solutions. Reporting directly to the Revenue Leader, you will oversee the sales organization, leading all unit acquisition activities and establish scalable processes to accelerate growth. The ideal candidate is a strategic sales leader with deep experience in FinTech, PropTech, or high-growth SaaS industries.

This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters. For candidates outside of the NY/NJ area, you may be eligible for our relocation assistance program.

What you’ll do

  • Develop and execute a strategic sales plan to drive revenue growth and expand Flex’s market presence.
  • Build, lead, and mentor a high-performing sales team, fostering a culture of accountability, collaboration, and excellence.
  • Define and optimize the sales process, implementing best practices and leveraging CRM tools to improve efficiency and pipeline visibility.
  • Establish strong relationships with key stakeholders in the rental real estate industry, including property managers, real estate investors, and industry partners.
  • Own and drive enterprise and mid-market sales cycles, from prospecting through contract negotiation and closing.
  • Collaborate with Marketing, Product, and Partner Success teams to align sales strategies with company goals and ensure seamless customer onboarding.
  • Analyze sales data and performance metrics to refine strategies, improve forecasting, and drive continuous improvement.
  • Represent Flex at industry events, conferences, and networking opportunities to enhance brand visibility and thought leadership.
  • Identify emerging market trends, competitive threats, and new business opportunities to inform long-term strategy.

Key qualifications

  • 15+ years of experience, with at least 7 years in a leadership role within FinTech, PropTech, or SaaS industries.
  • Proven track record of driving significant revenue growth and scaling high-performance sales teams.
  • Strong ability to build and nurture executive-level relationships within enterprise accounts.
  • Expertise in complex B2B sales cycles, with a consultative approach to selling.
  • Deep understanding of sales operations, forecasting, and pipeline management.
  • Ability to coach and mentor existing sales organization and develop a program to manage top talent.
  • Exceptional communication, negotiation, and leadership skills.
  • Experience with CRM tools (e.g., Salesforce) and data-driven sales methodologies.
  • High level of initiative, self-motivation, and the ability to thrive in a fast-paced, dynamic environment.
  • Experience with managing both revenue targets and other critical OKR deliverables at the same time.
  • Ability to thrive in a fast-paced, high-growth environment and adapt to evolving business needs.

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/CA, the base salary pay range will be $248,000 - $267,000. 

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. For full time, U.S. based employees we offer:

  • Competitive pay
  • 100% company-paid medical, dental, and vision
  • 401(k) + company equity
  • Unlimited paid time off with a PTO minimum + 13 company paid holidays
  • Parental leave 
  • Flex Cares Program: Non-profit company match + pet adoption coverage
  • Free Flex subscription

 For full time non-US employees, we offer

  • Competitive Pay
  • Company Equity
  • Unlimited PTO

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