Head of Advertising Strategy & Operations

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.

Responsibilities

• 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.

Qualifications

• 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.

Benefits and Working Arrangements

Enjoy private healthcare and dental insurance, a generous work from abroad policy, share purchase plans, an electric vehicle scheme, extra festive time off, and family friendly benefits. We prioritize career growth with clear career paths, transparent pay bands, personal learning budgets, and regular learning days. We operate a hybrid model and ask that employees work from the office at least 60% of the time over a 12 week period, and we also have a 28 day work from abroad policy.

Equality, Diversity and Inclusion

We know that having a diverse team makes us better and helps us succeed. We include all forms of diversity-gender, ethnicity, sexuality, disability, nationality, and diversity of thought-and we are committed to creating inclusive places to work where everyone belongs and differences are valued and celebrated.