Sales Strategy & Planning Manager - Advertising

About us

At Trainline, our purpose is to empower greener travel choices, connecting people and places. 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 🚄 

We’re Europe’s leading independent rail platform, helping millions of travellers find and book the best-value rail and coach journeys across our app, website and partner channels.

Our job is to make the green travel choice the best choice. By building a better train travel experience, we help more people choose rail - creating a positive impact for customers, our business and the planet.

We’re a team of more than 1,000 Trainliners from over 50 nationalities, working across London, Paris, Barcelona, Milan, Edinburgh and Madrid. Now is a brilliant time to join us and help shape the future of travel.

Introducing the Trainline Media Team 👋

Trainline Media has proven advertiser demand and is now focused on building a larger, more predictable and repeatable sales engine. This role is central to that next phase, improving how the team plans, prioritises and manages sales performance so that sellers are focused on the right advertisers, generating high-quality opportunities and taking the actions needed to deliver revenue goals.

You will act as the commercial operating partner to Trainline Media's sales leadership and sales team, working backwards from revenue targets to define the pipeline, prospecting and sales activity required to deliver the plan. This is a hands-on, individual-contributor role with no direct reports, where success depends on combining rigorous analysis with strong commercial judgement, and on influencing experienced sellers without managing them directly. You will work closely with Sales, Marketing, Finance and Client Success to remove barriers to revenue.

In this role as the Sales Strategy & Planning Manager, you will...🚄

• 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.

We'd love to hear from you if you have...🔍

• 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.

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!