Director, Legal - Commercial

About Us Highland Electric Fleets’ mission is to make electric fleets accessible and affordable for all, enabling communities to realize the benefits of cleaner, quieter and healthier fleets. Highland is North America’s leading provider of Electrification-as-a-Service (EaaS). Founded in 2019, Highland partners with school districts, municipalities, and fleet operators to make the transition to electric fleets simple and affordable. Highland proudly serves as the Official Electric School Bus Provider of the LA28 Olympic and Paralympic Games and Team USA. From pioneering vehicle-to-grid technology to managing some of the nation’s largest electric school bus fleets, Highland delivers reliable, cost-effective solutions that support local communities and drive the future of transportation. Summary: Highland has an opportunity for a seasoned commercial counsel with an entrepreneurial mindset. This Director role reports to the General Counsel and supports our core business in driving revenue contracts with public agencies and transportation firms. The ideal candidate will have at least six years of legal experience, including law firm and in-house roles as well as supervisory experience. The candidate should be comfortable navigating strategic partnerships, drafting and negotiating a variety of commercial contracts, and supporting related financings. Experience in one or more of the following industry areas is strongly preferred: transportation, fleet leasing, or energy services (such as power purchase agreements, battery storage, or energy savings contracts). The candidate will work in a fast-paced startup environment and will be comfortable taking on an array of matters. However, the primary focus in this role will be to collaborate with Highland’s sales and origination team and counterparties to drive the sales process from preliminary negotiations (or bid solicitation response) to executed contracts. Key Responsibilities: Establish and manage key commercial alliances, including formal and informal partnerships and joint ventures; Serve as a thought partner to the executive team in ongoing development of commercial strategy and product; Lead deal structuring, navigating business and customer constraints to develop creative commercial solutions; Draft and negotiate transportation equipment services agreements; Oversee commercial contract product offerings, including updates and versioning of forms; Support market development team in crafting RFP responses for vehicle electrification-as-a-service and related requests; Draft and negotiate other contracts supporting sales (LOIs, teaming arrangements, license/lease agreements); Provide pragmatic, business-minded guidance on contract-related issues; Assist with pilot programs in product development and R&D Support special and ancillary services projects, including stationary storage and other energy optimization solutions; and Supervise one or more attorney(s) and/or legal professional(s) in support of the above responsibilities. Other responsibilities may include: Support financing and M&A transactions, including collaborating with internal stakeholders on drafting matters, responding to due diligence inquiries, and managing outside counsel; Develop support materials and provide training to educate the sales and origination team members on contract terms and other legal issues; Support continued development of scalable contracting strategies and tools in coordination with legal operations and the commercial team; Tackle new areas of growth and product development; and Support other legal team members in a dynamic and collaborative environment. Required Qualifications: 8-10+ years as a practicing attorney JD with membership in at least one U.S. state bar (MA preferred) Excellent commercial negotiation and contract drafting skills Executive-level business acumen and judgment Exceptional accuracy and attention to detail Ability to work flexibly with a variety of internal and external stakeholders and to manage multiple matters simultaneously Prior experience supervising attorneys and/or legal professionals Legally authorized to work in the United States without current or future employer sponsorship Preferred Qualifications: Industry experience in one or more of the following: transportation, fleet leasing, or energy services Prior experience executing in a fast-paced, high-ambiguity environment Ability and availability to work at least two (2) days a week in-office at the company’s Beverly, MA headquarters* *For highly qualified candidates, fully remote work may be considered with periodic travel to Beverly HQ required. What You Can Expect from Highland: Competitive base salary and performance-based bonus program A supportive, highly collaborative, team-oriented environment Ability to work with bright, innovative, and forward-thinking colleagues Health, Vision, and Dental coverage for employees & their dependents Generous Paid Time Off 401(k) program and company match Highland Electric Fleets provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. In addition to federal law requirements, Highland Electric Fleets complies with applicable state and local laws governing nondiscrimination in employment. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.