Holiday Extras
Head of Software Delivery
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Salary: £95,059 - £118,824 DOE + Benefits + Bonus
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
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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!
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How we hire for this role
We know your time is precious, so we keep our recruitment process as quick and easy as possible. If we believe you might be a match for a job you’ve applied for, you’ll enter our hiring process as follows:
- Interview with Recruitment Lead & PDLT member
- Panel interview & presentation with COO & Product Director
- Final meet the team
Cultivating a diverse and inclusive culture is paramount for us.
Recognising we are all different, if for whatever reason you need us to adapt the process, please get in touch via recruitment@holidayextras.com.
Why choose Holiday Extras?
We believe that holidays are the most precious time of all, so we create products, tech and services that make travel and holidays memorable and fun. We’re on a mission to be the only place to go for your holiday extras, offering unparalleled choice, value and service, turning our customers’ ordinary trips into extraordinarily good times.
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
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