Senior Ads Sales Planning & Operations Manager

About the role

The Senior Ads Sales Planning & Operations Manager acts as the commercial operating partner to Trainline Media's sales leadership and sales team, translating high-level revenue ambitions into actionable plans. This role owns the end-to-end sales performance management process, from defining pipeline requirements to running rigorous sales reviews that drive corrective action. You will be responsible for building and maintaining a prioritised prospect universe, ensuring every seller focuses on the highest-value opportunities. Success in this position depends on combining rigorous analysis with strong commercial judgement to influence experienced sellers without direct management. You will partner cross-functionally to remove barriers, introduce data-driven improvements, and own the frameworks that make the sales engine predictable. The role involves introducing AI-assisted tools and reusable playbooks to sharpen pitches and personalise outreach at scale. Ultimately, you will build the analytical dashboards and reporting cadences that give leadership complete visibility into capacity, productivity, and revenue risk.

Key facts

What you'll do

• Translate annual and quarterly revenue targets into clear pipeline, prospecting and account-planning requirements, and run the sales-performance reviews that keep the team focused on the right actions.
• Define and track the leading and lagging indicators used to manage commercial performance, giving leadership a clear view of capacity, productivity and revenue risk.
• Build and maintain a prioritised prospect universe across advertisers, agencies and verticals, helping each seller focus on the accounts most likely to convert.
• Own pipeline standards, forecasting methodology and commercial reporting, improving the quality of opportunity data in Salesforce and giving leadership an honest view of committed, likely and upside revenue.
• Analyse where the team spends its time and reallocate effort toward the highest-value selling activity.
• Introduce AI-assisted tools and reusable frameworks that sharpen pitches, personalise outreach at scale and simplify repetitive sales processes.
• Partner with Sales, Marketing, Finance and Client Success to remove barriers to revenue and share learnings that improve how the team sells.
• Build analytical dashboards that track sales effectiveness, productivity and the impact of the tools and processes you introduce.
• Develop scenario models to evaluate trade-offs between capacity, conversion rates, and deal size, supporting more informed resourcing decisions.
• Own the governance rhythm for pipeline reviews, forecast accuracy checks, and stakeholder reporting, ensuring consistent and transparent communication.
• Collaborate with Marketing to align demand generation output with the sales pipeline plan and measure the quality of inbound opportunities.
• Work closely with Finance to model revenue outcomes, validate pricing assumptions, and ensure forecasts reflect the latest commercial realities.
• Liaise with Client Success to surface expansion signals and ensure account plans incorporate retention and growth opportunities.
• Standardise sales playbooks and enablement materials, making it easier for sellers to execute a consistent, high-quality approach.
• Track adoption and usage of new tools and processes, iterating based on feedback and performance outcomes.

Requirements

• Experience in sales strategy, sales operations, revenue operations or commercial planning, ideally within media, advertising or adtech.
• Strong analytical skills, with fluency in pipeline, forecasting, conversion and productivity metrics.
• Hands-on comfort with Salesforce and BI (business intelligence) reporting tools.
• A track record of turning revenue targets into concrete plans, and using data to decide where a sales team should focus its time.
• Real commercial judgement, understanding what makes a pitch land and helping sellers sharpen their story as well as their numbers.
• Practical curiosity about AI and automation, ideally with examples of using new tools to make a sales team faster and more effective.
• The credibility and influence to challenge and guide experienced sellers without managing them directly.
• A highly organised, self-directed style, and genuine comfort operating as a hands-on individual contributor.
• Demonstrated ability to manage multiple priorities in a fast-paced, deadline-driven environment while maintaining a high standard of accuracy.
• Strong written and verbal communication skills, with experience tailoring messages for executives, managers, and individual contributors.
• Comfort working with large data sets and drawing insights that inform action.
• Commitment to maintaining data integrity and process discipline even as the business scales quickly.
• Willingness to collaborate across functions and cultures in a diverse, international team.
• Understanding of the rail travel market and the needs of business customers in the travel sector is advantageous.

Practical notes

• 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.
• We're operating a hybrid model and ask that Trainliners work from the office a minimum of 60 percent of the time.
• Please note that this description is intended to outline the general nature and level of work performed within this role and does not specify all responsibilities, duties, or skills required, nor does it exclude any applicable laws, policies, or regulations.

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