Head of Advertising Strategy & Operations

Requirements

• 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.

What the job involves

• 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.
• 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.