Company: Trainline

Apply for the Head of Legal – 12 month Fixed Term Contract

Location: London

Job Description:

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.

Introducing the Trainline Legal Team

At Trainline, our Legal team plays a critical role in enabling growth across Europe by helping the business to navigate complex regulatory landscapes, unlock commercial opportunities, and build trusted relationships with industry partners. As we continue to expand across non-UK markets, Legal works closely with teams across the business to shape strategy, support market entry, and ensure we can move forward with confidence in an evolving regulatory environment.

Head of Legal – Role Overview

Reporting into the Deputy General Counsel, this Head of Legal role is a strategic leadership opportunity supporting Trainline’s European growth ambitions on a fixed term basis during a period of maternity leave. Operating at the intersection of regulation, commercial strategy and market expansion, you’ll help shape the business approach across multiple markets, translating complex and evolving frameworks into clear, pragmatic action that supports growth, product development and commercial outcomes.

Responsibilities

Support Trainline’s regulatory and competition strategy across the EU, shaping how the business navigates and influences evolving frameworks to influence commercial strategy and market expansion.
Use legal and regulatory strategy as an enabler for growth and to accelerate innovative customer and industry propositions.
Act as a senior escalation point for complex commercial contract negotiations, providing pragmatic and solutions-oriented legal guidance on high impact issues to shape commercial outcomes.
Partner cross‑functionally with commercial, product and government relations teams to execute strategic priorities outside the UK.
Lead and support a collaborative, high‑performing legal team culture in line with our Team Charter, providing guidance to direct reports while representing Legal as a credible and confident advisor to the business.
Drive continuous improvement across legal processes, including the adoption of AI and legal technology tools to improve efficiency, scalability, and business partnership.

Qualifications

Strong experience advising on EU regulatory matters, ideally within complex, fast‑moving, or highly regulated industries.
Deep understanding of how legal and regulatory developments shape commercial strategy and market positioning.
A preference for operating in areas of ambiguity, using sound judgment where precedent may be limited.
A commercially minded approach to legal partnership, with experience balancing legal risk alongside growth, market opportunity, and customer impact.
Experience supporting sophisticated commercial negotiations and providing business‑facing legal advice to senior stakeholders.
Strong leadership and stakeholder management skills, with the ability to influence across multiple functions and communicate effectively at all levels.
A hands‑on, collaborative approach and a willingness to challenge constructively, support decision‑making, and act as an enabling partner to the business.

Benefits

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’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.

Values

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.

Diversity & Inclusion

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.