Commercial Counsel

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 2026 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 We are seeking a seasoned commercial counsel with deep expertise in commercial transactions and fintech to join our in-house Legal Compliance team as a strategic leader. At this level, you will help own the strategy and operational direction of Flex's commercial contracting function — not just executing on existing processes, but defining how they should evolve. You will be a key thought partner to the VP Legal and senior business leaders across revenue, finance, treasury, privacy, corporate governance, and emerging regulatory matters. This is an exceptional opportunity for a commercially-minded attorney ready to lead with both legal depth and operational vision. You will help shape how our legal team scales, build best-in-class processes and tooling, and pioneer the use of AI to transform how Flex handles contract review, negotiation, and insights. You will act as a key connector between Legal and the broader organization, influencing decisions that extend well beyond the legal department. 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 Own the strategic and operational direction of Flex's commercial contracting function, driving policy, standards, and outcomes across customer, vendor, and partner agreements. Lead the design and implementation of AI-powered legal workflows , including contract review automation, AI-assisted negotiation support, and data-driven contract insights — identifying innovative tools and methodologies to measurably increase legal team velocity and accuracy. Define and drive the legal technology roadmap for commercial and compliance operations; evaluate, select, and oversee deployment of contract lifecycle management (CLM) platforms, AI review tools, and legal analytics systems. Partner with senior business leaders across Revenue, Finance, Product, and Operations to provide proactive, strategic legal counsel — identifying legal risks before they become business problems. Set the legal standards and playbooks for commercial contracting across the company, ensuring consistency, scalability, and alignment with Flex's risk posture and regulatory obligations. Provide mentorship and structured guidance to more junior members of the legal team on commercial matters, contract strategy, and effective use of legal technology. Monitor the evolving legal and regulatory landscape — including consumer lending, data privacy, and fintech regulation — and translate developments into actionable recommendations for the business. Lead cross-functional strategic projects in coordination with internal stakeholders and external counsel, managing multiple workstreams with significant business impact. Drive continuous improvement in how the legal function operates, championing a culture of efficiency, innovation, and high standards. Key qualifications 7 - 10+ years of combined experience at a top-tier law firm and in-house legal department, with a focus on commercial and corporate matters and some experience across general legal matters. Background in fintech, payment or proptech industries; experience with consumer lending, structure ... (truncated, view full listing at source)