Position OverviewWeDriveU is seeking a highly skilled Contract & Compliance Attorney to support our growing transportation operations with a focus on government contracting, bid support, regulatory compliance, and commercial legal matters. This role will partner closely with business development, operations, and leadership teams to provide strategic legal guidance throughout the contract lifecycle-from proposal development and contract negotiations through execution and dispute resolution.
The successful candidate will advise on all aspects of federal, state, and local government contracting, including Requests for Proposals (RFPs), Requests for Qualifications (RFQs), cooperative purchasing programs, and negotiated procurements. Responsibilities include identifying legal and commercial risks in procurement documents; advising on bid responsiveness and responsibility requirements; evaluating contract exceptions; interpreting procurement statutes, regulations, and agency policies; supporting competitive procurements and protests; negotiating contract terms, amendments, renewals, and change orders; advising on equitable adjustments and claims; and providing practical guidance on contract performance, compliance, and enforcement.
The ideal candidate will have experience supporting government contracts, public transportation, paratransit, shuttle, and mobility operations, with a strong understanding of public-sector procurement and compliance with applicable federal, state, and local transportation laws and regulations. This includes experience with Federal Transit Administration (FTA) requirements, Federal Motor Carrier Safety Administration (FMCSA) regulations, state departments of transportation and public utilities/public service commission requirements, ADA paratransit regulations, vehicle and driver compliance, operating authority and permitting, safety regulations, and other legal and regulatory requirements applicable to public transit, demand-response, commuter, and shuttle transportation services.
Key Responsibilities- Provide legal guidance and support for government contracting activities, including RFP reviews, proposal submissions, bid strategy, and contract negotiations.
- Partner with business development teams to review solicitation requirements, identify legal risks, and support competitive proposal responses.
- Draft, review, and negotiate commercial agreements, subcontractor agreements, vendor contracts, and other business-related agreements.
- Advise operations teams on contract compliance obligations, performance requirements, and risk mitigation strategies.
- Monitor and interpret transportation-related regulations, including FTA, FMCSA, and other applicable federal, state, and local requirements.
- Support compliance initiatives, policies, procedures, and internal controls to ensure alignment with contractual and regulatory obligations.
- Assist with commercial disputes, claims management, and contract-related litigation matters.
- Collaborate with internal stakeholders and outside counsel on legal matters requiring specialized expertise.
- Provide practical, business-oriented legal advice to support operational and strategic objectives.
- Maintain awareness of changes in government contracting laws, transportation regulations, and industry trends.
- State DOT and Public Utilities/Public Service Commission regulations
- ADA complementary paratransit requirements
- Drug & Alcohol compliance (49 CFR Parts 40 and 655 where applicable)
- CDL and driver qualification requirements
- Vehicle inspections and maintenance compliance
- Operating authority, permits, and business licensing
- Safety Management Systems and regulatory reporting
- State-specific operating authority (e.g., CPUC, NYSDOT, etc., where applicable)
- Compliance with client contract requirements tied to regulated transit service
Required Qualifications- Juris Doctor (J.D.) degree from an accredited law school and active bar membership.
- 7+ years of legal experience, preferably with a focus on government contracting, commercial contracts, or transportation-related matters.
- Experience reviewing and supporting government contracts, RFPs, and procurement processes.
- Strong understanding of contract compliance, risk management, and regulatory requirements.
- Experience interpreting and applying transportation regulations, including FTA and/or FMCSA requirements.
- Excellent negotiation, communication, and analytical skills.
- Ability to translate complex legal requirements into practical business solutions.
Preferred Qualifications- Experience supporting the transportation, transit, fleet, mobility, or public-sector services industries.
- Experience with government agencies, municipal contracts, or public-private partnerships.
- Litigation, claims management, or dispute resolution experience.
- Familiarity with transportation operations, service contracts, and operational compliance requirements.
- Experience managing outside counsel and cross-functional legal projects.
We OfferPhysical Health- Exceptional Medical, Dental, Vision, and Life Insurance benefits
Financial Health- Competitive compensation packages
- 401(k) with 4% employer match
- Financial Wellness Tool
- Commuter Benefits
Emotional Health- Employee Assistance Program (EAP)
- Unlimited PTO
- Paid holidays
- Pet & Legal Insurance
Personal Development- On-the-job training and skills development
- Internal transfer opportunities for career growth
*Benefits vary by position and location 
