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Head of Strategy - Legal & Compliance

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 Head of Strategy for our Legal & Compliance organization, you'll partner directly with the Chief Legal & Compliance Officer to develop and execute on the overall strategy. Your key responsibility will be to ensure urgent execution of our roadmap and to represent Legal & Compliance across the company, collaborating closely with teams in Product, Consumer Protection, Finance, and beyond. You’ll also have opportunities for end-to-end ownership of key strategic projects. Given Flex operates at the intersection of highly regulated industries—consumer finance, housing, and payments—Legal & Compliance is central to every aspect of our enterprise and critical to Flex’s most important initiatives. This role will provide frequent exposure to Flex Founders and Executive Team, giving hands-on experience of what it takes to lead and operate a world-class consumer fintech.

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

  • Partner with your department leader (Chief Legal & Compliance Officer) to set long-range strategy and translate it into tangible near-term goals and frameworks that ensure tight execution
  • Manage a diverse portfolio of projects (e.g., Enterprise AI strategy, Pricing), adapting rapidly to shifting priorities 
  • Own complex special projects that may require: some understanding of legal and compliance topics, ability to navigate and align with cross-functional stakeholders, make a recommendation, and push through execution 
  • Continuously improve processes, streamline collaboration, and identify ways to improve the capacity and velocity of the Legal and Compliance teams
  • Conduct research and prepare communications for senior legal and compliance executives, the executive team, and the board of directors, ranging from company updates to in-depth presentations and data analysis
  • Distill progress into executive-facing monthly memos, facilitating the review meetings to ensure the right strategic conversations are had
  • Communicate effectively with senior stakeholders, navigating complex problem sets with agility
  • Operate at top-decile levels of speed and productivity, dealing constructively with pressure and debate

Who You Are

  • Ideally 5+ years of relevant work experience (e.g., investment banking, management consulting, start-up role in strategy, strategic finance, biz ops, or chief of staff function) 
  • Direct work (or advisory experience) with a high-growth tech/fintech company preferred
  • Advanced degree (JD, MBA) a plus
  • Strong conceptual facility; extremely fast thinker
  • Comfort “fog sculpting,” making amorphous projects tractable 
  • Entrepreneurial; finds the messiness of 0-to-1 building exhilarating 
  • Obsessive attention to detail; high bar for your own work product 
  • Well honed interpersonal skills; able to drive results through others without compromising relationships and rapport
  • Ability to thrive in a fast-paced (and at times chaotic) environment 
  • Strong bias for action 
  • Superior communication skills (e.g., memos, meeting facilitation)

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 $196,000 - $213,000. For all other states, the base salary pay range will be $176,000 - $190,000.

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 + 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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