Senior Director, Head of Risk & Compliance

The Director of Risk Management is responsible for developing, leading, and continuously improving WeDriveU's enterprise rick and compliance program. This role provides oversight of the operational, regulatory, contractual, and organizational risks across the company's transportation operations and ensures that compliance expectations are translated into clear, practical operating procedures.

Director of Risk Management will work closely with Operations, Safety, Maintenance, Human Resources, Legal, Procurement, Finance, and other business leaders to identify risk, strengthen controls, prepare for audits, and address compliance concerns before they affect employees, customers, service delivery, or the company's reputation.

This leader must be able to balance strong regulatory discipline with the practical realities of operating a complex, multi-state transportation organization. The role requires someone who can move beyond identifying issues and build sustainable solutions that improve accountability and operational performance.

Key Responsibilities

Risk Management Strategy and Governance

• Develop and maintain an enterprise compliance framework aligned with applicable federal, state, local, contractual, and customer requirements.
• Establish clear compliance ownership, accountability, policies, controls, reporting standards, and escalation protocols across the organization.
• Maintain an inventory of applicable regulatory and contractual obligations and assign responsible business owners.
• Provide senior leadership with clear reporting on compliance performance, emerging risks, audit findings, corrective actions, and areas requiring executive attention.
• Advise leadership on the compliance implications of new contracts, acquisitions, operating models, service expansions, and market entries.
• Promote a culture in which compliance is integrated into day-to-day business decisions and operating practices.
• Maintain visibility into key regulatory, contractual, operational, financial, and reputational risks across the organization.

Transportation Regulatory Compliance

• Oversee compliance with applicable U.S. Department of Transportation, Federal Motor Carrier Safety Administration, Federal Transit Administration, state transportation, and local operating requirements.
• Provide governance over driver qualification, commercial driver's license, medical certification, motor vehicle record, hours-of-service, controlled substances and alcohol testing, Drug and Alcohol Clearinghouse, vehicle inspection, maintenance, and record-retention requirements.
• Partner with Safety, Operations, Maintenance, Human Resources, and Recruiting to ensure employees performing safety-sensitive work meet all applicable qualification and testing requirements.
• Monitor changes in transportation regulations and determine the operational impact on company policies, systems, training, and procedures.
• Support compliance with customer-specific transit requirements, public agency obligations, and federally funded transportation program requirements where applicable.
• Maintain appropriate oversight of third-party administrators, testing providers, background screening partners, subcontractors, and other vendors performing compliance-related services.

Risk Assessment Audit and Monitoring

Develop a risk-based compliance audit and monitoring program covering corporate functions and operating locations.

Lead or coordinate internal audits, customer reviews, regulatory inspections, and compliance assessments.

Establish standardized audit tools, testing methods, documentation requirements, and reporting processes.

Track findings through closure and verify that corrective actions are timely, complete, and sustainable.

Identify recurring or systemic issues and work with business leaders to address root causes rather than relying on temporary corrections.

Conduct targeted reviews when performance data, complaints, incidents, or control failures indicate increased risk.

Conduct periodic risk assessments to identify areas of increased regulatory, operational, contractual, financial, or reputational exposure.

Partner with business leaders to develop practical mitigation plans for identified risks and control weaknesses.

Evaluate the severity, likelihood, and potential business impact of identified risks to help prioritize corrective actions and resources.

Policies, Procedures, and Training

Develop, review, and maintain compliance policies, standards, procedures, and operating guidance.

Ensure policies are practical, clearly communicated, and consistently implemented across locations.

Partner with Learning and Development and business leaders to create required compliance training for employees, managers, and safety-sensitive personnel.

Provide guidance to leaders regarding the interpretation and application of compliance requirements.

Evaluate whether policy or training changes are needed following audits, incidents, regulatory developments, or identified control gaps.

Investigations and Corrective Action

Lead or support investigations involving potential regulatory violations, falsification of records, control failures, conflicts of interest, or other compliance concerns.

Coordinate investigations with Legal, Human Resources, Safety, Security, Internal Audit, and Operations as appropriate.

Maintain confidential and complete investigation records.

Recommend corrective action based on the facts, level of risk, applicable requirements, and consistency of company practices.

Escalate significant violations or patterns of noncompliance to senior leadership.

Support disclosures, response plans, or remediation activities when required by regulators, customers, or contractual partners.

Contract and Customer Risk

Partner with Legal, Business Development, Operations, and Procurement to evaluate compliance obligations contained in customer contracts, requests for proposals, and vendor agreements.

Support the development of compliance plans for new contracts and operational launches.

Establish processes to ensure required licenses, permits, certifications, reports, and customer deliverables remain current.

Monitor compliance with disadvantaged business enterprise, accessibility, Title VI, equal employment opportunity, safety, drug and alcohol, and other public transportation requirements where applicable to the contract.

Serve as a senior point of contact during customer compliance reviews and regulatory audits.

Data, Systems, and Risk Reporting

Define compliance metrics and dashboards that provide leadership with meaningful visibility into performance and risk.

Use data to identify trends, recurring findings, overdue actions, documentation gaps, and higher-risk operating locations.

Partner with Technology, Human Resources, Safety, and Operations to improve the accuracy and integration of compliance-related systems and records.

Establish controls over sensitive compliance information and ensure access is limited to authorized personnel.

Regularly assess whether compliance processes can be standardized, automated, or simplified without weakening controls.

Develop and maintain risk registers, heat maps, or similar reporting tools that allow leadership to understand and prioritize significant risks.

Leadership and Partnership

Build and lead a capable compliance function aligned with the size and risk profile of the organization.

Develop strong working relationships with operational leaders and act as a practical, credible compliance advisor.

Clarify the responsibilities of corporate departments, field leadership, and local operating teams.

Provide direct and constructive feedback when practices create unacceptable risk.

Represent WeDriveU professionally with regulators, customers, auditors, and external partners.

Develop team members and establish clear performance expectations and succession plans.

Required Qualifications

Bachelor's degree in business, law, transportation, safety, risk management, public administration, or a related field.

At least 10 years of progressively responsible experience in risk management, compliance, transportation, safety, legal, audit, or a closely related function.

Strong knowledge of transportation regulatory requirements and operational risk in a multi-state environment.

Experience supporting a geographically dispersed, multi-state operation.

Demonstrated experience developing risk and compliance controls, audit programs, corrective action plans, and executive reporting.

Experience responding to regulatory audits, customer reviews, investigations, or government inquiries.

Strong judgment and the ability to assess legal, regulatory, operational, financial, and reputational risk.

Ability to interpret complex requirements and convert them into clear operating expectations.

Strong written, verbal, presentation, and executive communication skills.

Ability to travel regularly to company locations and customer sites.

Preferred Qualifications

Juris Doctor, master's degree, or other relevant advanced degree.

Relevant professional certification in risk management, compliance, audit, safety, or a related discipline.

Experience in passenger transportation, public transit, motor carrier operations, fleet services, school transportation, paratransit, or another safety-sensitive industry.

Familiarity with Safety Management Systems and public transportation agency safety requirements.

Experience working with unionized operations and government or public agency contracts.

Experience implementing compliance technology, automated monitoring, or enterprise risk systems.

About WeDriveU

WeDriveU powers mobility for organizations across the United States, operating fixed route shuttles, on demand microtransit, and other passenger services that connect people to work, school, health care, and community. Our culture is safety first and people first. We invest in training, recognize great performance, and promote from within.

EEO and Accommodations

WeDriveU is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected status. If you need a reasonable accommodation for any part of the hiring process, please let us know.