The Head of Transformation Delivery is a senior leadership role responsible for driving Microlise's digital transformation agenda and the end-to-end delivery of the company's capital programmes. Reporting directly to the Chief Technology Officer, this role provides the governance, structure and executive-level visibility required to ensure strategic technology investments are delivered on time, on budget, and at the quality expected by the business.

The Head of Transformation Delivery acts as the connective tissue between Engineering, Product, Architecture, Go-to-Market and Data Science, translating strategy into a disciplined delivery operation and ensuring that investment cases are robust, well-governed, and aligned to Microlise's growth ambitions.

This is an initial 18-month Fixed Term Contract to deliver three critical transformational projects, Microlise One TMS, Data and AI Platform, and Fleet telematics for the mid market.

 What you'll be doing: 

 Digital Transformation Leadership

• Own and orchestrate the Microlise digital transformation programme, ensuring strategic alignment with the CTO's technology vision and the broader business strategy.
• Define and maintain a rolling programme roadmap, translating board-level priorities into structured, deliverable workstreams.
• Champion continuous improvement in delivery methodology, tooling and governance across all transformation initiatives.
• Act as a visible leader and advocate for change, helping teams navigate complexity and ambiguity throughout transformation cycles.

 Capital Programme Delivery & Governance

• Lead the delivery of all capital programmes within the technology portfolio, maintaining full accountability for programme scope, schedule, budget and risk.
• Establish and run an effective Programme Management Office (PMO) structure, including governance frameworks, RAID logs, tollgate reviews and escalation pathways.
• Manage a team of two direct reports and a broader community of Project Managers, providing clear direction, coaching and performance management.
• Ensure consistent, high-quality reporting of programme status to the CTO, ExCo and Board as required - including KPIs, milestone progress, budget variance, and risk posture.
• Drive rigorous benefits realisation tracking, ensuring programmes deliver the outcomes documented in approved investment cases.

 Reporting & Executive Communication

• Produce concise, insight-led programme reports for the CTO, Board and senior leadership, translating complex delivery data into clear narratives and actionable recommendations.
• Maintain a single consolidated view of all active capital programmes, providing real-time transparency on progress, dependencies, and risk across the portfolio.
• Prepare and present programme updates at ExCo, Board and investor-facing forums as required.
• Define and own programme performance metrics, ensuring a consistent and credible reporting cadence across the PMO.

 Stakeholder Relationships

• Build trusted, collaborative relationships with Heads of Product Management to ensure alignment between programme delivery and product strategy.
• Partner closely with the Head of Architecture to ensure all capital programmes are delivered in line with the approved architecture roadmap and target state.
• Work hand-in-hand with Engineering leadership (UK and India) to resource programmes appropriately, remove blockers and maintain delivery momentum.
• Engage Go-to-Market teams to ensure new capabilities land effectively with customers, with readiness and launch activities incorporated into programme plans.
• Build strong relationships with Finance, Legal and Commercial teams to support investment case development, approvals and contract governance.

 Business & Investment Cases

• Lead the development of high-quality business cases and investment cases for new capital programmes, strategic initiatives and growth opportunities.
• Structure cases to include clear problem statements, options appraisals, financial models, risk assessments, and benefit projections - to a standard suitable for Board approval.
• Work collaboratively with Product, Architecture, Engineering and Finance to ensure cases are technically credible, commercially sound and strategically compelling.
• Track and report on the realisation of approved business cases post-delivery, providing evidence of ROI to the CTO and Board.
• Champion a culture of evidence-based investment decision making across the technology function.

What we’re looking for:

• Proven experience delivering large-scale digital transformation programmes in a technology-led organisation.
• Strong track record of managing capital programmes end-to-end, including budget accountability, governance and stakeholder reporting.
• Experience managing and developing Project Managers, building high-performing delivery teams.
• Demonstrated ability to write and present investment and business cases to senior leadership and Board level.
• Exceptional communication and influencing skills - able to engage credibly with technical and non-technical stakeholders at all levels.
• Strong commercial acumen and financial literacy, including programme budgeting and benefits tracking.
• Deep understanding of programme governance frameworks (MSP, PRINCE2 or equivalent).
• Highly organised and structured - able to manage multiple complex workstreams simultaneously without losing sight of the detail.
• Resilient under pressure, with a calm and decisive approach to navigating risk and uncertainty.
• Collaborative by nature - builds bridges across functions and brings people with them through change.
• Commercially minded - understands the connection between technology delivery and business outcomes.
• Proactive and outcome-focused - drives programmes forward with energy and accountability.

Desirable

• Experience in SaaS, telematics, transport technology or logistics software environments.
• Familiarity with Agile delivery methodologies and hybrid programme management approaches.
• Exposure to M&A integration programmes or platform consolidation initiatives.
• MSP Practitioner, PRINCE2 Practitioner, PMP or equivalent programme management certification.
• Experience working across geographically distributed engineering teams.