At a Glance
- Tasks: Lead strategy cycles, shape key decisions, and drive impactful projects at Trainline.
- Company: Join a fast-growing tech company at the forefront of travel technology.
- Benefits: Competitive salary, career-defining role, and exposure to senior leadership.
- Other info: Opportunity to define your role and influence across teams.
- Why this job: Make a real impact on strategic direction in a high-performing team.
- Qualifications: 3-7 years in management consulting or strategy, strong analytical skills.
The predicted salary is between 80000 - 100000 € per year.
Requirements
- 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
- (Desirable) Experience running a strategy cycle in a matrixed tech organisation
- (Desirable) An MBA or equivalent postgraduate qualification
- (Desirable) Language skills in French, Italian or Spanish
- (Desirable) Experience working with or shaping strategy in an AI driven environment
What the job involves
This position will sit in our Commercial Finance team, reporting into the VP of Finance. At Trainline, it is not just about reporting numbers; Commercial Finance is at the centre of how we grow, make decisions, and define our future. This is a high performing, high impact team that combines analytical rigour with sharp commercial instinct. We partner closely with leaders across the business, helping shape some of the most important decisions Trainline makes. The bar is high, and so is the opportunity to do meaningful, visible work.
This role is a rare opportunity to step into a truly career defining position. It sits at the intersection of strategy, finance, and leadership, with direct exposure to the VP Finance, CFO, and wider executive team. You will be working on the questions that matter most, with the space and support to shape the answers. As a newly defined role, there is real scope to build and define what great looks like. You will own the annual strategy process end to end, set the agenda for the biggest strategic questions we face, and lead the thinking that guides where Trainline goes next.
Success in this role comes from the quality of your ideas, the depth of your analysis, and your ability to influence at the highest levels. If you are looking for a role where you can stretch yourself, operate at pace, and have a genuine impact on the direction of a fast growing tech business, this is it.
Owning the annual strategy process
- 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
Leading strategic projects and commercial analysis
- 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
- Partner with other teams as a trusted strategic partner to Product, Marketing, Commercial, and Tech teams
- Bring an external perspective on market trends, competition, and the wider travel technology landscape
- Support the VP Finance and CFO with independent, well-informed strategic thinking
Shaping how we tell our story
- Create clear and compelling materials for the C suite and Board
- Support the Board strategy process, including timelines and content development
- Partner with Investor Relations to shape the external narrative and ensure it reflects our ambition
Embedding strategy into the business
- Own key business rhythms such as MBRs and QBRs, ensuring they drive accountability and progress
- Track performance against our North Star and strategic priorities
- Work with teams to help land strategic initiatives in a practical and effective way
Head of Strategy in London employer: Deepstreamtech
At Trainline, we pride ourselves on being an exceptional employer that fosters a dynamic and inclusive work culture. As the Head of Strategy, you will have the unique opportunity to influence key decisions at the highest levels while working alongside a high-performing team dedicated to driving growth and innovation in the travel technology sector. With a strong emphasis on employee development, we offer ample opportunities for professional growth and the chance to make a meaningful impact in a fast-paced environment.
StudySmarter Expert Advice🤫
We think this is how you could land Head of Strategy in London
✨Tip Number 1
Network like a pro! Reach out to people in your industry, especially those who work at Trainline or similar companies. A friendly chat can open doors and give you insights that might just help you land that Head of Strategy role.
✨Tip Number 2
Prepare for interviews by practising your storytelling skills. You’ll want to showcase your analytical prowess and strategic thinking, so have examples ready that highlight your experience in management consulting and financial modelling.
✨Tip Number 3
Don’t underestimate the power of follow-ups! After an interview, send a thank-you note to express your appreciation and reiterate your enthusiasm for the role. It shows you’re genuinely interested and can set you apart from other candidates.
✨Tip Number 4
Apply through our website! It’s the best way to ensure your application gets seen by the right people. Plus, it shows you’re proactive and really keen on joining the team at Trainline.
We think you need these skills to ace Head of Strategy in London
Some tips for your application 🫡
Tailor Your CV:Make sure your CV is tailored to the Head of Strategy role. Highlight your experience in management consulting or strategy, and don’t forget to showcase those analytical and financial modelling skills we’re looking for!
Craft a Compelling Cover Letter:Your cover letter is your chance to shine! Use it to explain why you’re the perfect fit for this role. Talk about your experience with strategy cycles and how you’ve influenced decisions in previous roles.
Showcase Your Problem-Solving Skills:In your application, give examples of how you’ve tackled complex problems in the past. We want to see your structured approach and how you’ve formed clear conclusions that led to impactful decisions.
Apply Through Our Website:Don’t forget to apply through our website! It’s the best way for us to receive your application and ensures you’re considered for this exciting opportunity. We can’t wait to see what you bring to the table!
How to prepare for a job interview at Deepstreamtech
✨Know Your Numbers
Make sure you brush up on your analytical and financial modelling skills. Be prepared to discuss how you've built models from scratch in the past and how they generated meaningful insights. This will show that you can handle the data-driven aspects of the role.
✨Master the Art of Simplification
Practice presenting complex topics in a simplified manner. You might be asked to explain intricate strategies or financial concepts to senior stakeholders, so being able to break these down without losing depth is crucial. Use examples from your previous experience to illustrate this skill.
✨Showcase Your Strategic Influence
Prepare to discuss specific instances where you've influenced decisions across teams. Highlight your experience in running strategy cycles and how you've partnered with various departments. This will demonstrate your ability to work collaboratively and lead strategic initiatives.
✨Be Ready for Scenario Analysis
Expect to engage in discussions about evaluating new opportunities and making data-driven recommendations. Brush up on your scenario analysis skills and be ready to present a clear, structured approach to problem-solving. This will showcase your strategic thinking and decision-making capabilities.
