Head of Fleet and Compliance

Stobart (Part of the Culina Group) is a leading ambient transport and logistics business, providing services to many of the UK’s best known brands across core consumer and retail sectors.

At Culina we have a winning culture, we believe that our culture is one of the reasons our company continues to thrive… A place where you're valued, challenged, and inspired!

Job Description

The Head of Fleet and Compliance is responsible for providing strategic leadership, governance, and oversight of fleet compliance, operator licensing, transport regulation, and fleet administration activities across all Eddie Stobart Ltd operations throughout the United Kingdom and Ireland.

The Head of Fleet and Compliance will provide leadership, coaching, and professional development to Transport Managers, Fleet Administration Teams, Compliance Auditors, and operational stakeholders, fostering a culture of accountability, continuous improvement, safety and compliance excellence across all operating centres.

Key Accountabilities / Responsibilities include:

Strategic Leadership & Governance

• Lead and maintain the organisation's fleet governance and transport compliance framework, ensuring robust controls are in place across all operating centres.
• Provide strategic leadership for transport compliance, fleet governance, and regulatory assurance activities across the business.
• Develop, implement, and continuously improve transport compliance policies, standards, and processes in line with legislative requirements, industry best practice, and ISO 9001 accreditation.
• Drive the adoption of a culture of accountability, continuous improvement, safety, and professional excellence throughout all transport operations.
• Develop and deploy effective transport governance, assurance, and performance review processes at all levels of the business

Operator Licence Management & Regulatory Compliance

• Safeguard all Operator Licences by ensuring full compliance with licence undertakings, regulatory obligations, and organisational policies.
• Act as the authorised company signatory for Operator Licence matters and oversee all licence applications, variations, Transport Manager applications, and related regulatory submissions.
• Monitor, interpret, and communicate legislative, regulatory, and industry developments, ensuring business readiness and compliance with evolving requirements.
• Lead engagement with the Driver and Vehicle Standards Agency (DVSA), Office of the Traffic Commissioner, Police, enforcement agencies, and other regulatory bodies.
• Manage regulatory investigations, Public Inquiries, audits, interventions, and notifiable events, ensuring effective governance and timely resolution.

Compliance Assurance & Risk Management

• Oversee compliance risk management activities, including Operator Compliance Risk Score (OCRS) monitoring, corrective action planning, and performance improvement programmes.
• Manage the organisation's central transport compliance systems, ensuring effective utilisation, data integrity, continuous improvement, and operational excellence.
• Lead internal and external compliance audit programmes through the Compliance Audit function, ensuring consistency, objectivity, and operational engagement.
• Oversee targeted improvement initiatives and corrective actions to address identified compliance shortfalls and mitigate risk.
• Ensure effective regulatory reporting, governance controls, and compliance assurance activities are maintained across the fleet operation.

Fleet Compliance & Stakeholder Management

• Work collaboratively with fleet providers, maintenance providers, and operational stakeholders to ensure compliance with Operator Licence commitments and legislative obligations.
• Provide expert guidance and support to Transport Managers and operational teams on legal compliance, fleet governance, and regulatory requirements.
• Develop strong relationships with internal and external stakeholders to ensure effective delivery of compliance objectives and business priorities.
• Represent the organisation on transport compliance matters with customers, regulators, industry bodies, and enforcement agencies as required.

Leadership & Team Development

• Lead, develop, and inspire high-performing Transport Managers, Compliance Auditors, Fleet Administration Managers, and Fleet Administration teams.
• Establish clear objectives, performance standards, and development plans that support organisational goals and continuous professional development.
• Promote succession planning, capability development, and professional excellence across all compliance and fleet administration functions.
• Drive engagement, accountability, and ownership within teams to deliver outstanding compliance and governance outcomes.

Reporting & Performance Management

• Deliver meaningful compliance reporting, analysis, and assurance information to Executive Leadership, Board members, and senior stakeholders.
• Monitor fleet compliance performance, identify emerging trends and risks, and provide strategic recommendations to support informed decision-making.
• Measure and report on compliance effectiveness, audit outcomes, corrective action progress, and organisational compliance maturity.

Finance

• Full ownership for preparing and managing the central transport legal compliance budget.
• Ensure financial probity and value for the Stobart pound is obtained through our compliance systems.
• Liaise with our central IT teams on the contracts for our Compliance systems.

Qualifications

Experience:

Essential

• Minimum 5 years' experience within transport compliance, fleet management, transport operations, or regulatory governance roles.
• Significant senior management experience within a large HGV fleet operation holding multiple Operator Licences across the UK and/or Ireland.
• Proven experience managing Transport Managers, compliance teams, fleet administration functions, or equivalent professional departments.
• Experience leading Operator Licence applications, variations, Transport Manager appointments, and regulatory submissions.
• Experience of successfully managing DVSA investigations, Traffic Commissioner Public Inquiries, compliance audits, and enforcement interventions.
• Experience developing and implementing transport compliance strategies, governance frameworks, and assurance programmes.
• Proven track record of improving compliance performance and reducing regulatory risk across multi-site operations.
• Experience presenting compliance performance and risk reports to Executive Leadership and Board-level stakeholders.

Desirable

• Experience within a national logistics, distribution, supply chain, or road haulage organisation operating large commercial vehicle fleets.
• Experience supporting mergers, acquisitions, business start-ups, or significant operational change programmes.
• Experience implementing digital transport compliance systems and business intelligence reporting solutions.

Qualifications

Essential

• International Transport Manager CPC (National and International).
• Full UK Driving Licence.
• Evidence of ongoing Continuous Professional Development (CPD).

Desirable

• Degree or equivalent qualification in Transport Management, Logistics, Business Management, Compliance, or related discipline.
• Lead Auditor qualification (ISO 9001 or equivalent).
• Membership of an accredited professional body such as CILT, SOE, IoTA, Logistics UK, or RHA.
• NEBOSH, IOSH or equivalent health and safety qualification.

Additional Information

As part of our drive to make Stobart a great place to work. We are proud to be an inclusive and diverse organisation where we are committed to employee development and recognising success for hard working performers.

Our dedicated learning and development programmes are open to every employee to give you the opportunity to shape your own future within logistics and continue to work in an environment where team culture thrives.

Our People are the driving force behind our success, which is why we offer a wide range of benefits which include:

• Private Medical Cover – This gives you peace of mind, you have choice, flexibility and speed of access to the most clinically appropriate care via Bupa
• Company Bonus – We do our best work to succeed together. When we achieve our goals you'll be rewarded through our bonus scheme
• Car Allowance
• Pension scheme – we want colleagues to enjoy a comfortable retirements so we offer a great contribution
• Life Assurance - x 4 your annual salary
• Wellness – Via our Employee Assistance Programme we offer immediate access to a confidential telephone counselling and legal information service that operates 24 hours a days, 365 days a year
• Eye Care Vouchers – We can provide you with substantial savings with free eye tests and discounts on prescription glasses
• Reward & Recognition – We recognise that employees have gone the extra mile via Employee of the month and year, special recognition and long service awards.

If you meet the requirements for the above role and are looking for your next career opportunity please apply now and become a part of our #WinningTeam!