Head of Learning & Development

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.

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.

Qualifications and Experience Desired

• 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.

Benefits and Work Conditions

• Enjoy fantastic perks like private healthcare and 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 are 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.
• 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.