Head of Advertising Strategy & Operations

About us We are champions of rail, inspired to build a greener, more sustainable future of travel. Trainline enables millions of travellers to find and book the best value tickets across carriers, fares, and journey options through our highly rated mobile app, website, and B2B partner channels. Great journeys start with Trainline 🚄 Now Europe’s number 1 downloaded rail app, with over 135 million monthly visits and £6.3 billion in annual ticket sales, we collaborate with 270+ rail and coach companies in over 40 countries. We want to create a world where travel is as simple, seamless, eco-friendly and affordable as it should be. Today, we're a FTSE 250 company driven by our incredible team of over 1,000 Trainliners from 50+ nationalities, based across London, Paris, Barcelona, Milan, Edinburgh and Madrid. With our focus on growth in the UK and Europe, now is the perfect time to join us on this high-speed journey. Introducing the Trainline Advertising Team 👋 Every month, millions of travellers plan, book and take journeys through Trainline, creating valuable moments for brands to connect with customers in a relevant and trusted way. Trainline Advertising has already proven its model, built repeat business, and is now scaling into a more mature, repeatable and high-margin commercial engine across multiple European markets. As Head of Ads Strategy & Operations , you will help connect ad sales, product development, operations and client delivery to ensure Trainline Advertising scales with clarity, consistency and commercial impact. You will shape go-to-market plans, support the development and commercialisation of new ad propositions, lead operational excellence, and build high-performing teams across Ads Strategy, Account Management and Operations. In this role as the Head of Ads Strategy & Operations, you will...🚄 Support the Ads Proposition Strategy Lead in shaping go-to-market strategy, helping ensure Trainline Advertising develops compelling propositions that meet advertiser needs and create differentiation in the market. Develop sales enablement materials, including narratives, playbooks, training decks and communication plans, to equip Ad Sales teams with clear and commercially effective messaging. Partner closely with sales leadership to strengthen pipeline visibility, forecast accuracy and conversion, helping unblock demand and support delivery against commercial targets. Set and evolve operational standards for ad delivery, measurement, quality, reliability and service levels across direct and programmatic campaigns. Lead and develop the Operations and Client Success teams, setting clear priorities, ways of working and development plans that enable the function to scale sustainably. Shape the strategy for the ad tech stack, including Google Ad Manager, SSPs, DSPs, consent frameworks and measurement tools, ensuring the platform remains resilient and fit for future growth. Own key ad tech partner relationships, including performance, costs and commercial negotiations, while working with teams to maintain a privacy-first approach across GDPR, TCF v2.0 and evolving frameworks. Drive client retention and growth by ensuring strong post-sale delivery, proactive account management, campaign optimisation, reporting, renewals and insight-led client conversations. We'd love to hear from you if you have...🔍 Significant experience in retail media, digital publishing, ad tech or platform advertising, with a track record of helping scale a business beyond its early stage. Experience leading teams across a broad remit, ideally including commercial strategy, account management, client success and ad operations. Strong commercial judgement, with experience supporting revenue growth, margin improvement, pricing, yield, pipeline discipline and senior leadership reporting. A strong understanding of the ad tech ecosystem, including Google Ad Manager, SSPs, DSPs and programmatic delivery models, with the confidence to set direction and challenge detail. Good knowledge of privacy-first advertising, consent management and relevant frameworks such as GDPR and TCF v2.0. Experience building operational rigour, scalable processes, documentation and resilience into a growing business. Confidence operating in ambiguity, creating clarity for others and influencing outcomes across teams where you may not hold direct authority. Excellent stakeholder management skills, with the ability to translate between technical and commercial audiences and influence product, sales and operational priorities. More information: Enjoy fantastic perks like private healthcare & 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. Jump on board and supercharge your career from day one! We're operating a hybrid model 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. Our values represent the things that matter most to us and what we live and breathe everyday, in everything we do: 💭 Think Big - We're building the future of rail ✔️ Own It - We focus on every customer, partner and journey 🤝 Travel Together - We're one team ♻️ Do Good - We make a positive impact 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. Interested in finding out more about what it's like to work at Trainline? Why not check us out on LinkedIn , Instagram and Glassdoor !