Fractional Commercial Counsel

Department: Corp Ops - Finance

Reports to: CFO

Location: Remote

FLSA Status: Non-Exempt (Hourly)

As our in-house Commercial Counsel, you will play a critical role in accelerating revenue by enabling the business to close deals faster and smarter. This is a highly cross-functional, business-facing role where success is measured not just by risk mitigation—but by how effectively you help the company win and execute deals.

At One Rail, you won't sit on the sidelines. You'll be embedded in the business, helping shape how we scale revenue while protecting the company in a thoughtful, modern way.

• Own the Contract Lifecycle: Draft, review, and negotiate a wide range of commercial agreements, including MSAs, SaaS agreements, NDAs, SOWs, and vendor contracts
• Enable Sales Velocity: Partner closely with Sales, Customer Success, and Finance to move deals forward efficiently without unnecessary friction
• Negotiate with Judgment: Identify real risks vs. perceived risks and apply practical, business-oriented solutions
• Standardize & Scale: Develop contract templates, fallback positions, and playbooks that streamline negotiations and reduce cycle times
• Advise the Business: Provide clear, actionable guidance to internal stakeholders—translating legal language into business impact
• Balance Risk & Growth: Protect the company while enabling smart, calculated risk-taking in support of revenue goals
• Collaborate Cross-Functionally: Work closely with the CFO, sales leadership, and external counsel when needed
• Continuously Improve: Identify bottlenecks in the contracting process and implement scalable improvements

• 3–6 years of experience in commercial contracting (law firm or in-house)
• Experience reviewing and negotiating B2B SaaS and/or enterprise commercial agreements
• J.D. from an accredited law school and active bar membership
• Strong familiarity with common contracting areas (liability, indemnity, data privacy, SLAs, etc.)
• Ability to operate independently in a fast-paced, high-growth environment

• Experience in logistics, supply chain, or transportation technology
• Prior experience as an in-house counsel supporting a sales organization
• Exposure to data security and privacy frameworks

This role will likely average 10-15 hours per week, with the expectation of the hours increasing with company growth. Remote position with occasional travel to One Rail headquarters in Orlando, Florida required for onboarding and as-needed basis thereafter.