Head of Business Risk Strategy at Flexcar – Boston, New York

Job Title: Head of Business Risk Strategy
Location: On-site 5 days/week in Boston, MA or New York, NY
Position Type: Full-time Exempt – 50 hours/week
Compensation: $175K - $230K * + Bonus + Full Benefits Package
This role will be leveled, with compensation aligned to experience and demonstrated capabilities.
Flexcar is completely reimagining car ownership. We offer the world’s first month-to-month car lease, with insurance and maintenance included. Members can swap cars anytime as their needs change, without the commitment or hassle of traditional car ownership. By combining operational expertise with technology, data, and AI, we’re transforming every aspect of the customer journey and delivering a more affordable, flexible, and hassle-free alternative to buying or leasing.

Why Join Us
We are building a modern platform where thoughtful risk decisions enable innovation, speed, and long-term value. Risk here is not a gatekeeper—it is a strategic partner. You’ll work directly with senior leaders to shape how we grow, who we serve, and how our products operate in the real world.

The Role
We’re looking for a Business Risk Strategist who brings sharp commercial judgment, product-oriented thinking, and the ability to influence high-stakes decisions. This is a cross-functional, strategy-focused role shaping how we evaluate opportunities, design guardrails, and make confident go / no-go decisions. You’ll act as a trusted thought partner.

What You’ll Do

• Partner with Product, Legal, and Senior leadership on market, customer, and product go / no-go decisions
• Design and evolve risk frameworks and decision systems that enable speed and value creation
• Apply strong business acumen to assess competition, customer expectations, and market dynamics
• Identify when existing processes are no longer effective and redesign them for scale
• Communicate risk tradeoffs clearly and challenge decisions constructively
• Take ambiguous initiatives from concept through execution

What We’re Looking For

• 7 plus years of overall experience in management consulting (BCG, McKinsey, Bain, or similar) and/or risk, product, or strategy roles in fintech or high-growth tech
• Demonstrated experience influencing real business outcomes—not just conducting analysis
• Strong commercial judgment and comfort operating in ambiguous environments
• Product-centric mindset with the ability to assess how systems operate in practice
• Executive presence, independent thinking, and confidence engaging senior stakeholders
• Ability to own work end-to-end and see initiatives through completion

Nice to Have

• Experience supporting or evaluating AI-enabled products from a business perspective
• Early-stage or scale-up company experience
• Background in platform, commercial, or product risk

Why This Role Is Unique

• Direct access to senior leadership and influence on company strategy
• Modern, forward-looking view of risk as a business enabler
• High-impact role shaping how we evaluate customers, partners, and new opportunities
• Opportunity to define what excellent risk looks like in a growing company

What Tops Off the Tank

• Rest & Relaxation: Flexible PTO policy.

• Future Savings: Benefit from a 401(k) plan with company match from day one.

• Benefits: Excellent, low-cost healthcare coverage including : medical, dental, vision, eligibility day one.

• Drive a Flexcar! Discounted employee rate on Flexcar products and no annual membership fee and other amazing perks!
  Disclaimer: This job description may not be inclusive of all assigned duties, responsibilities, or aspects of the job described, and may be amended at any time at the sole discretion of the Employer.

Flexcar is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. Flexcar provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.