Head of Strategy

Introducing Commercial Finance at Trainline. This position will sit in our Commercial Finance team, reporting into the VP of Finance. At Trainline, it is not just about reporting numbers; Commercial Finance is at the centre of how we grow, make decisions and define our future. This is a high performing, high impact team that combines analytical rigour with sharp commercial instinct. We partner closely with leaders across the business, helping shape some of the most important decisions Trainline makes. The bar is high, and so is the opportunity to do meaningful, visible work. This role is a rare opportunity to step into a truly career-defining position. It sits at the intersection of strategy, finance and leadership, with direct exposure to the VP Finance, CFO and wider executive team. You will be working on the questions that matter most, with the space and support to shape the answers. As a newly defined role, there is real scope to build and define what great looks like.

You will own the annual strategy process end to end, set the agenda for the biggest strategic questions we face, and lead the thinking that guides where Trainline goes next. Success in this role comes from the quality of your ideas, the depth of your analysis, and your ability to influence at the highest levels. If you are looking for a role where you can stretch yourself, operate at pace, and have a genuine impact on the direction of a fast growing tech business, this is it.

What you will be doing:

• Owning the annual strategy process: Lead Trainline’s annual strategy cycle from start to finish, shaping the approach, timeline and final output for leadership and Board. Design and run strategy workshops with senior leaders, bringing together perspectives into a clear multi-year plan. Partner with Finance, Product, Commercial and Operations to ensure priorities are clearly defined and owned. Establish a clear rhythm to track progress against strategic priorities and long term ambitions.
• Leading strategic projects and commercial analysis: Identify and evaluate key opportunities such as new markets, products or partnerships, answering “should we do this” with clear, data driven recommendations. Lead strategic projects from hypothesis through to Board level output. Build robust financial models and scenario analysis to support decision making. Translate complex analysis into clear, impactful materials for senior stakeholders. Support M&A and corporate development activity as needed.
• Partnering across the business: Act as a trusted strategic partner to Product, Marketing, Commercial and Tech teams. Bring an external perspective on market trends, competition and the wider travel technology landscape. Support the VP Finance and CFO with independent, well informed strategic thinking.
• Shaping how we tell our story: Create clear and compelling materials for the C suite and Board. Support the Board strategy process, including timelines and content development. Partner with Investor Relations to shape the external narrative and ensure it reflects our ambition.
• Embedding strategy into the business: Own key business rhythms such as MBRs and QBRs, ensuring they drive accountability and progress. Track performance against our North Star and strategic priorities. Work with teams to help land strategic initiatives in a practical and effective way.

What you will bring:

• 3 to 7 years of experience in management consulting or in-house strategy within a listed or high growth business.
• Strong analytical and financial modelling skills, with the ability to build models from scratch and generate meaningful insight.
• A structured approach to solving complex problems and forming clear, well reasoned conclusions.
• Experience contributing to or owning strategy or planning cycles.
• Confidence presenting to senior stakeholders and simplifying complex topics without losing depth.
• A track record of influencing and partnering across teams.

It is a bonus if you have:

• Experience running a strategy cycle in a matrixed tech organisation.
• An MBA or equivalent postgraduate qualification.
• Language skills in French, Italian or Spanish.
• Experience working with or shaping strategy in an AI driven environment.

Enjoy fantastic perks like private healthcare and dental insurance, a generous work from abroad policy, 2-for-1 share purchase plans, an EV scheme to further reduce carbon emissions, extra festive time off, and excellent family-friendly benefits. We prioritise career growth with clear career paths, transparent pay bands, personal learning budgets, and regular learning days. We operate a hybrid model to work and ask that Trainliners work from the office a minimum of 60% of their time over a 12-week period. We also have a 28-day Work from Abroad policy. We know that having a diverse team makes us better and helps us succeed. And we mean all forms of diversity - gender, ethnicity, sexuality, disability, nationality, and diversity of thought. That's why we're committed to creating inclusive places to work, where everyone belongs and differences are valued and celebrated.