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?
As a Strategic Account Executive at Flex, you will play a critical role in driving revenue growth and expanding our presence within the rental real estate sector. This senior-level sales position is responsible for engaging and closing high-value enterprise accounts, developing long-term strategic partnerships, and working closely with cross-functional teams to ensure customer success. The ideal candidate has a strong background in enterprise sales, a history of exceeding revenue targets, and experience managing complex sales cycles with executive stakeholders.
What you’ll do- Identify, target, and engage key enterprise accounts within the rental real estate industry to drive revenue growth.
- Own the entire sales cycle, from prospecting and initial outreach to negotiation, closing, and contract execution.
- Build and maintain relationships with C-level executives, property management firms, and key decision-makers.
- Conduct high-impact sales presentations and product demonstrations to showcase the value of Flex’s solutions.
- Collaborate with Marketing, Product, and Customer Success teams to ensure a seamless sales process and client onboarding.
- Manage a strategic sales pipeline, utilizing CRM tools to track progress and accurately forecast revenue.
- Develop and execute account-specific sales strategies to maximize adoption and engagement.
- Consistently exceed sales quotas and revenue targets.
- 8+ years of enterprise sales experience, preferably in FinTech, PropTech, or SaaS industries.
- Proven track record of consistently exceeding quotas and driving substantial revenue growth.
- Strong ability to build and nurture executive-level relationships within enterprise accounts.
- Excellent communication, presentation, and negotiation skills.
- Ability to navigate complex sales cycles and manage multiple stakeholders.
- High level of initiative, self-motivation, and the ability to thrive in a fast-paced, dynamic environment.
- Experience leveraging various outbound prospecting channels, including phone, email, and social media.
- Proficiency with CRM tools (e.g., Salesforce) and data-driven sales methodologies.
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 range will be $194,000-$244,000,
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
Similar Jobs
What you need to know about the Boston Tech Scene
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
