Commercial Counsel

Job Description - Commercial Counsel

Overview

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

As Commercial Counsel, you will be a key member of Flex’s growing Legal & Compliance team. Your primary mission is to own Flex’s commercial contracting function from proposal to signature, and to scale that function through playbooks, policies, and technology — including AI-assisted workflows. You will take proactive ownership of your scope, contribute to large cross-functional legal projects, and drive continuous improvements to how the legal department operates.

This opportunity is ideal for an entrepreneurial attorney who wants to build, not just execute. You will be empowered to design and implement tools and processes that measurably increase team velocity, and your manager will be intensely focused on your development and career growth at Flex.

For roles based in NYC, SF, and Salt Lake City: This is a hybrid position with on-site expectations of 3 days per week in our offices in NYC, San Francisco, and Salt Lake City. For candidates outside of these areas, you may be eligible for our relocation assistance program.

What you’ll do

• Optimize, oversee and maintain all aspects of the company’s customer and vendor contracting cycles, including the negotiation and drafting of services and other commercial agreements.
• Build out and maintain contracting playbooks, policies and frameworks for the escalation of complex requests, repository management.
• Design and implement AI-assisted legal workflows for the team — including prompt templates, contract review checklists, and automated intake pipelines — and train team members on effective and compliant AI use. Identify where AI output requires escalation or attorney review, and build appropriate oversight into workflows.
• Help build the foundation of a best-in-class legal team, including our in-house commercial function.
• Keep the department and business apprised of new laws and regulations that could have an impact on the company’s commercial business, both regionally and nationally.
• Voice your opinion and a drive for continuous improvement.
• Close strategic deals by finding pragmatic solutions to any issue you encounter.
• Adapt to change in a fast paced, dynamic environment.
• 3 - 5+ 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.
• Experience with consumer lending, fintech, or proptech is a plus.
• Demonstrated ability to use AI tools for legal tasks (contract review, research, drafting) and to design AI‑assisted workflows; able to craft effective prompts, critically evaluate AI output, and apply good judgment before relying on AI-generated work.
• Preference for candidates able to work out of our NYC, SF, or Salt Lake City offices on a hybrid basis.
• Strong interpersonal skills to build productive cross‑functional relationships, with a strong tolerance for sarcasm and dry humor.
• Coachable, with a willingness to learn and improve.
• Persistence, drive and a goal‑focused mindset as you own projects from initiation to completion.
• Strong attention to detail and ability to effectively prioritize tasks within a fast‑paced environment.
• Ability to work independently and as part of a team.
• A bias for action, clear and concise communication skills, and a willingness to prioritize what truly matters.
• JD from an accredited law school and member in good standing of a US state bar.

Flex takes a market‑based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 markets (NYC/ SF) , the base salary pay range for this role is $184,000—$230,000 USD . For all other U.S. locations, Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the Tier 1 states listed above, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location.

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.

Offices

Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on‑site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program.

For full‑time U.S. employees we offer:

• Competitive medical, dental, and vision
• Company equity
• 401(k) plan with company match
• 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‑U.S. employees, we offer:

• Competitive compensation + company equity
• Unlimited PTO