Head of Strategy

Trainline

Head of Strategy at Trainline responsible for leading the annual strategy cycle and defining strategic priorities. Collaborating with senior leadership to shape business direction in the travel industry.

Posted 5/9/2026full-timeLondon • 🇬🇧 United KingdomLead💰 £100,000 - £120,000 per yearWebsite

About the role

Key responsibilities & impact

Lead Trainline’s annual strategy cycle from start to finish, shaping the approach, timeline and final output for leadership and Board
Design and run strategy workshops with senior leaders, bringing together perspectives into a clear multi year plan
Partner with Finance, Product, Commercial and Operations to ensure priorities are clearly defined and owned
Establish a clear rhythm to track progress against strategic priorities and long term ambitions
Identify and evaluate key opportunities such as new markets, products or partnerships, answering “should we do this” with clear, data driven recommendations
Lead strategic projects from hypothesis through to Board level output
Build robust financial models and scenario analysis to support decision making
Translate complex analysis into clear, impactful materials for senior stakeholders
Support M&A and corporate development activity as needed
Act as a trusted strategic partner to Product, Marketing, Commercial and Tech teams
Create clear and compelling materials for the C suite and Board
Support the Board strategy process, including timelines and content development
Own key business rhythms such as MBRs and QBRs, ensuring they drive accountability and progress

Requirements

What you’ll need

3 to 7 years of experience in management consulting or in house strategy within a listed or high growth business
Strong analytical and financial modelling skills, with the ability to build models from scratch and generate meaningful insight
A structured approach to solving complex problems and forming clear, well reasoned conclusions
Experience contributing to or owning strategy or planning cycles
Confidence presenting to senior stakeholders and simplifying complex topics without losing depth
A track record of influencing and partnering across teams
Bonus: Experience running a strategy cycle in a matrixed tech organisation
Bonus: An MBA or equivalent postgraduate qualification
Bonus: Language skills in French, Italian or Spanish
Bonus: Experience working with or shaping strategy in an AI driven environment

Benefits

Comp & perks

Private healthcare & dental insurance
Work from abroad policy
2-for-1 share purchase plans
EV Scheme to further reduce carbon emissions
Extra festive time off
Excellent family-friendly benefits
Clear career paths
Transparent pay bands
Personal learning budgets
Regular learning days

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

financial modelingdata analysisscenario analysisstrategic planningproblem solvingmarket evaluationM&A supportstrategy workshopsimpactful presentationstrategy cycle management

Soft Skills

analytical skillscommunication skillsinfluencing skillspartnering skillsstructured thinkingconfidencecollaborationaccountabilityleadershipsimplifying complex topics

Certifications

MBApostgraduate qualification