---
title: 'Director, Legal - Commercial at Highland Electric Fleets'
canonical: 'https://feeny.ai/job/director-legal-commercial-highland-electric-fleets-beverly-me458t57bxdn'
type: 'job'
last_seen: '2026-09-10'
---

# Director, Legal - Commercial at Highland Electric Fleets

- **Company:** Highland Electric Fleets
- **Location:** Beverly, MA
- **Compensation:** $200k–$230k
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-09-01
- **Last confirmed live:** 2026-09-10
- **Apply:** https://jobs.lever.co/highlandfleets-2/aef6ceeb-9765-4bad-a4d7-cb350dd905cf

## Job description

## 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.

## About Highland Electric Fleets

## Company Overview
- **One-liner**: Highland Electric Fleets is North America’s leading provider of Electrification-as-a-Service (EaaS), partnering with school districts, municipalities, and fleet operators to transition diesel fleets to electric.
- **Entity Type**: Private (Venture-backed; latest round: $75M preferred equity, June 2026)
- **Headquarters**: Beverly, Massachusetts, United States
- **Founded**: 2019
- **Founders**: Duncan McIntyre

## Core Business
- **Primary industry/industries**: Transportation Programs, Fleet Electrification, Clean Energy Infrastructure
- **Target customers**: B2G (Business-to-Government) — primarily school districts, municipalities, and municipal fleet operators across North America
- **Mission or purpose statement**: "Make electric fleets accessible and affordable for all communities" [highlandfleets.com](https://highlandfleets.com/about-us/)

## Products & Services
- **Electrification-as-a-Service (EaaS)**: A full-service, long-term contract model covering planning, procurement, implementation, and ongoing optimization of electric fleets. Includes vehicles, charging infrastructure, software, and operational support — all bundled at a cost comparable to traditional diesel.
- **Vehicle-to-Grid (V2G) Integration**: Technology enabling electric school bus batteries to feed power back to the grid, creating an additional revenue stream for fleet operators and supporting grid stability.
- **Major Event Transportation Operations**: Managing large-scale electric fleet operations for events, including serving as the Official Electric School Bus Provider for the LA28 Olympic and Paralympic Games.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Key Metric**: **Total Funding** — $478M across 4 rounds (most recent: $75M from Galvanize Climate Solutions in June 2026)
- **Notable Investors/Partners**:
  - Galvanize Climate Solutions (lead, 2026 preferred equity)
  - Aiga Capital Partners (lead, prior preferred equity)
  - LA28 Olympic and Paralympic Games (official provider)
  - Team USA
- **Growth Signals**:
  - Electric school buses have traveled **over 10 million miles** to date [cbinsights.com](https://www.cbinsights.com/company/highland-electric-transportation)
  - Active deployments in California, Colorado, Massachusetts, Michigan, New Jersey, New York, and Texas
  - 121 employees (stable headcount, +0.6% YoY)
  - 12,934 LinkedIn followers (+10.5% yearly growth)
  - $150M in total preferred equity commitments structured for long-term asset-backed deployment

## Competitive Advantages
- **First-mover scale**: Manages some of the nation’s largest electric school bus fleets, with proven reliability across diverse climates (Florida to Michigan to California).
- **EaaS business model**: Long-term service agreements create predictable, recurring revenue and reduce financial risk for customers by matching electric fleet costs to traditional fuel costs.
- **Vertical integration**: Owns the full stack — vehicles, charging, software, V2G, and operations — making switching costs very high for clients.
- **Major event credential**: The LA28 Olympic selection provides unmatched brand validation and operational experience at global scale.
- **Asset-backed financing**: Capital structure designed specifically for long-term, large-scale infrastructure deployment, a moat against undercapitalized competitors.

## Strategic Focus
- **National expansion**: Deploying electric school buses and charging infrastructure into new U.S. markets.
- **Municipal fleet diversification**: Broadening capabilities beyond school buses into other municipal fleet and energy applications.
- **Energy infrastructure integration**: Advancing projects that combine charging infrastructure with on-site energy resources (solar + storage) for customers.
- **Scaling asset portfolio**: Using the latest $75M capital injection to accelerate vehicle and charger deployments.

## Why Work Here
- **Mission-driven impact**: Directly contributes to reducing childhood asthma, improving local air quality, and combating climate change — measurable community outcomes.
- **Hybrid work model**: Flexible remote/office balance; headquarters in Beverly, MA, with roles listed as hybrid or remote.
- **Exceptional benefits**:
  - **100% premium coverage** for medical, dental, and vision (employees + dependents)
  - Long-Term Disability & Life Insurance
  - Flexible Spending/Saving Accounts
  - 3% Employee-Sponsored 401k Match
  - Stock Options
  - $100/mo Cell Phone Reimbursement
- **Work-life balance**:
  - 15 Paid Vacation Days
  - 10 Paid Holidays
  - 6 Paid Sick Days
  - Bonus week off between Christmas and New Year’s
  - 8 Weeks Paid Parental Leave (birthing parents get up to 16 weeks total)
- **Culture**: "Everybody serves" — each employee gets one paid day of service per year. Innovation and practical ingenuity are core values. In-person employee engagement annually. DEI opportunities available.
- **Current open roles** (as of search date): EV Field Service Technician (Hybrid, Boston), Project Finance Analyst (Hybrid, Beverly), Sr. Manager FP&A and Treasury (Remote, Beverly), General Manager Major Event Operations [jobs.lever.co](https://jobs.lever.co/highlandfleets-2)

## Sources
1. [highlandfleets.com - About Us](https://highlandfleets.com/about-us/)
2. [highlandfleets.com - Careers](https://highlandfleets.com/careers/)
3. [jobs.lever.co - Open Positions](https://jobs.lever.co/highlandfleets-2)
4. [cbinsights.com - Company Profile](https://www.cbinsights.com/company/highland-electric-transportation)
5. [linkedin.com - Company Page](https://linkedin.com/company/highlandelectricfleets)

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