Head of Transformation Delivery

Head of Transformation Delivery (Fixed Term Contract)

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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.

Why Microlise?

When your groceries arrive at your door or you sign for your online parcel, one or more of our software, telematics or proof-of-purchase solutions has probably been used. Our solutions deliver value to many of the UK’s leading grocery retailers and food logistics providers as well as to household names including JCB, Eddie Stobart, Carlsberg, Waitrose and Tesco.

Proudly Midlands-based, Microlise has been operating for over thirty years, and recently became a Publicly Listed Company with shares trading on the London Stock Exchange. Our growing business is guided by our culture which drives the way we behave, the way we work, the way we connect with our customers, and the way we support and develop our people.

Full support and training to ensure you are well equipped to succeed in your role

Private medical insurance with Vitality Health including rewards for members such as: Free Amazon Prime, Apple Watch, discounted gym membership and many more

33 days holiday, including bank holidays, increasing year on year to 38 days, then further increases with length of service

Life Assurance, 4 times your annual salary

Free Costco membership, 20% off EE mobile and line rental, and other discounts with Reward Gateway

Invested in employee health and well-being with over 20 mental health first aiders in the business

Employee Assistance Programmes

Great staff extras: Easter eggs, yearly BBQ, Christmas gifts, annual staff awards and many more incentives

Free Microlise Cresswell Racing Tickets, support British Superbikes

Executive Box at Motorpoint Arena Nottingham

Great Place to Work™ certified – We have been recognised by the global authority on workplace culture, so come be a part of our success

Best Workplace in the UK™ for Development, Technology, Wellbeing and Women

Recruitment Process

For successful candidates, interviews will take place whilst the advert is still live, so early application is encouraged.

Recruitment Agencies

Whilst we make every effort to directly source candidates for our live roles, we maintain a small preferred supplier list. We do not accept speculative CVs or unsolicited contact