Head Of Software Delivery

Holiday Extras; Folkestone; On-site; GBP 90,000 - 130,000; Full time

Benefits offered by this job

Pizza Fridays

Profit sharing

Pension scheme

Gym discounts

Hybrid/Office campus

Job summary

Holiday Extras is seeking a Head of Software Delivery to run the delivery system and rhythm for Product Development. You will collaborate with Product, Engineering, Architecture and IT to provide visible, structured delivery and informed decision-making across initiatives.

You will unite strategic work, platform, security and health into a coherent delivery picture, leading agile delivery, improving planning and surfacing risks early for the leadership team.

Qualifications

• Experience coordinating delivery of complex initiatives with multiple teams.
• Translate business objectives into actionable delivery plans with milestones.
• Clear and concise communication for senior leaders and teams.
• Ability to surface risks and dependencies early with owners.
• Strong organisational skills to create structure and momentum.

Responsibilities

• Create and maintain one integrated view of Product Development delivery across strategic initiatives, platform and domain work, security and technical health.
• Own and coordinate the Product Development planning and operating rhythm, including planning cycles, PDLT inputs, delivery reviews, decision and action tracking, consistent communication and follow-through.
• Give PDLT clear, concise and reliable information about progress, forecasts, capacity, risks and the trade-offs requiring a decision.
• Surface dependencies and delivery risks early, with clear owners and next steps, establish clear escalation routes and help the right people reach decisions.
• Coordinate and report Product Development’s contribution to enterprise programmes, working closely with the leaders responsible for the overall programmes.
• Lead, support and develop a high- performing agile delivery team.
• Strengthen team-level planning, work breakdown, reviews, retrospectives, forecasting and continuous improvement.
• Establish pragmatic delivery standards and reliable use of tools and data, without imposing one way of working on every team.
• Use evidence to improve delivery health, quality, flow and predictability rather than measuring activity for its own sake.
• Build trusted relationships across Product Development and the wider business, turning complex delivery information into clear communication.
• Facilitate difficult cross-functional discussions and workshops so that they end with clear decisions, owners and actions.

Skills

Relationship building

Influence without authority

Delivery coordination

Progress reporting

Cross-functional collaboration

Agile delivery

Risk & dependency management

People leadership

Strategic planning

Job description

Office based, Hythe, Kent

We care deeply about inclusive working practices and diverse teams. If you'd prefer to work full-time, part-time or as a job-share, we'll facilitate this wherever we can - whether to help you meet other commitments or to help you strike a great work-life balance.

About

We’re looking for a Head of Software Delivery to run the delivery system and organisational rhythm for Product Development. As a key senior member of the Product Development Leadership Team (PDLT), you'll collaborate closely with leaders in Product, Engineering, Architecture and IT. You’ll create the shared visibility, structure and follow-through that help our teams deliver and enable our PDLT to make timely, informed decisions.

You’ll bring together our strategic initiatives, platform and domain work, security and technical health into one coherent delivery picture. You’ll lead our agile delivery team, improve the way teams plan and learn, and make sure risks, dependencies, capacity constraints and changes to forecasts are surfaced early.

This is a senior leadership role alongside Product, Engineering and Architecture. You won’t set product priorities or make technical decisions. You’ll make sure accountable leaders have the information, rhythm and delivery discipline to make good choices and follow them through.

The Role

By joining our team you’ll:

• Create and maintain one integrated view of Product Development delivery across strategic initiatives, platform and domain work, security and technical health
• Own and coordinate the Product Development planning and operating rhythm, including planning cycles, PDLT inputs, delivery reviews, decision and action tracking, consistent communication and follow-through
• Give PDLT clear, concise and reliable information about progress, forecasts, capacity, risks and the trade-offs requiring a decision
• Surface dependencies and delivery risks early, with clear owners and next steps, establish clear escalation routes and help the right people reach decisions
• Coordinate and report Product Development’s contribution to enterprise programmes, working closely with the leaders responsible for the overall programmes
• Lead, support and develop a high- performing agile delivery team
• Strengthen team-level planning, work breakdown, reviews, retrospectives, forecasting and continuous improvement
• Establish pragmatic delivery standards and reliable use of tools and data, without imposing one way of working on every team
• Use evidence to improve delivery health, quality, flow and predictability rather than measuring activity for its own sake
• Build trusted relationships across Product Development and the wider business, turning complex delivery information into clear communication
• Facilitate difficult cross-functional discussions and workshops so that they end with clear decisions, owners and actions

Requirements

What you can bring to our team:

• Strong relationship-building skills, with the ability to establish trust across teams, disciplines and levels of seniority
• The judgement and ability to challenge constructively, influence without relying on authority and work through disagreement
• Experience coordinating the delivery of complex initiatives involving multiple teams, dependencies, priorities and stakeholders
• Experience helping and facilitating translation of business objectives into clear, sequenced and actionable delivery plans, with defined outcomes, dependencies, responsibilities and milestones
• Clear and concise communication, from translating complexity for senior leaders to giving teams useful context and direction
• Exceptional organisational skills, with a natural ability to create structure, maintain momentum and ensure decisions and commitments are followed through
• Strong people leadership, with experience coaching, developing and creating clarity for a team
• The ability to make incomplete or conflicting information visible and useful without creating false certainty
• Broad experience of different delivery approaches, with the judgement to choose and adapt the right techniques for the team, context and desired outcome
• Curiosity, and a willingness to change your approach as technology, AI and the needs of the organisation evolve
• A practical, evidence-led approach to improving how work flows, without imposing a standard method on every team
• Clear commercial, product and technology understanding to connect delivery decisions to customer and business outcomes

Everyone’s career path is individual and different, so this is just a guide. If your experience doesn't precisely match this, you’re encouraged to apply so that we can discover your unique talents!

Cultivating a diverse and inclusive culture is paramount for us.

Our roles are fully office based at our campus in Newingreen, in the heart of the Kent countryside - just minutes from Folkestone and the M20, where in person connection and collaboration is at the heart of how we work. You'll find free parking, an on-site café, and a state of the art campus that makes the commute worth it.

At Holiday Extras, we’re creating a workplace where everyone can thrive, build their careers and reach their limitless potential. As a Sunday Times Best Place to Work 2025, we’re proud to offer a world of benefits designed to enhance your lifestyle and well‑being. By joining our team, you’ll feel supported and rewarded every day. Learn more about our culture and benefits .

• Time is precious: 25 days annual leave (+BH’s), extra holidays through Holiday Buy, Birthday Day Off, and Sabbaticals at each milestone.
• Parental Leave: Enhanced parental leave - Up to 1 year off, including 13 weeks at 100% pay, 13 weeks at 50% pay
• Road to well-being: Access to Gym Discounts, Private Dental Insurance and Private Medical Insurance (after 4 years)
• Celebrate success together: Enjoy a Profit Share Bonus and a pension scheme with Aviva.
• Good for the soul: Join our Social Club for 25% off any ticket or event in the UK, Discounts on the latest tech, or give back to your community with our Volunteering Scheme.
• Plan ahead: Income protection, Critical illness cover and Life assurance