Head of Learning & Development

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 People Team

At Trainline, our People team plays a critical role in helping our business and colleagues thrive. We create the conditions for high performance, growth, and meaningful career development by building the capabilities, culture, and leadership needed to support our ambitious goals. As we continue to evolve, Learning & Development is a key enabler of organisational success, helping our people adapt, grow, and perform at their best.

As our Head of Learning & Development, you will define and lead Trainline’s learning strategy, ensuring it is closely aligned to business priorities and future capability needs. Reporting to the Director of People Partnering & L&D, you will partner closely with People Partners, leaders, and stakeholders across the organisation to deliver scalable, impactful learning solutions that drive measurable outcomes. This role combines strategic thinking with a practical, hands‑on approach, leading a small team while shaping the learning experiences, behaviours, and capabilities that will support Trainline’s continued growth and transformation.

In this role as the Head of Learning & Development, you will...

Learning Strategy & Business Alignment

• Define and lead Trainline's Learning & Development strategy and roadmap, ensuring capability‑building initiatives are aligned with business priorities, organisational goals, and future workforce needs.
• Partner closely with People Partners and business leaders to identify capability gaps and design targeted learning solutions that drive measurable business outcomes.
• Embed learning as a strategic enabler of performance, productivity, and organisational effectiveness, ensuring initiatives are commercially grounded and outcome‑focused.

AI & Future of Work Enablement

• Shape the learning strategy that supports AI adoption and evolving ways of working, helping colleagues and leaders build the skills, behaviours, and confidence needed to embrace new technologies.
• Develop scalable approaches to continuous learning and upskilling that enable Trainline to adapt to an increasingly dynamic business and technology landscape.

Performance & Leadership Development

• Design and embed learning interventions that strengthen leadership capability, enhance manager effectiveness, and support a high‑performance, feedback‑rich culture.
• Partner with People Partners and business leaders to build greater ownership and accountability for performance, coaching, and development across the organisation.

Learning Experience & Ecosystem

• Own and continuously evolve Trainline's learning ecosystem, including platforms, tools, external partnerships, and core learning journeys such as onboarding, leadership development, and compliance learning.
• Make informed build‑versus‑buy decisions that balance effectiveness, scalability, colleague experience, and return on investment.

Leadership & Stakeholder Partnership

• Lead, coach, and develop a high‑performing Learning & Development team, creating clarity of purpose while encouraging innovation and continuous improvement.
• Build trusted relationships with senior stakeholders across the business, influencing decision‑making and bringing external insight, emerging trends, and best practice into Trainline's approach to learning and development.

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

• Significant experience in Learning & Development, with deep expertise across learning strategy, leadership development, and organisational capability building.
• Experience operating at Senior Manager, Principal, Head of Learning & Development, or a similar leadership level, with responsibility for shaping and delivering impactful learning strategies.
• A strong track record of designing scalable learning frameworks, programmes, and operating models that deliver measurable business outcomes.
• Experience partnering with senior leaders, People teams, and cross‑functional stakeholders to diagnose needs, influence priorities, and co‑create effective solutions.
• Strong capability in leadership and manager development, with experience building learning interventions that improve performance and strengthen organisational culture.
• A good understanding of modern learning methodologies and learning technologies, alongside experience managing or evolving learning platforms and ecosystems.
• Experience supporting organisational transformation, behavioural change, digital adoption, or future of work initiatives, ideally including exposure to AI‑enabled ways of working.
• A commercially minded and pragmatic approach, with the ability to balance long‑term strategy with hands‑on execution and adapt effectively in a fast‑moving environment.

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!

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