At a Glance
- Tasks: Lead strategy processes, 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 opportunities, and exposure to senior leadership.
- Other info: Dynamic role with potential for significant career growth and influence.
- 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 required.
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 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 be part of a high-performing team that not only values analytical rigor but also encourages innovative thinking and collaboration across departments. With ample opportunities for professional growth and direct exposure to senior leadership, this role offers a unique chance to make a significant impact in a fast-paced, tech-driven environment.
StudySmarter Expert Advice🤫
We think this is how you could land Head of Strategy
✨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 need to present complex ideas clearly, so think about how you can simplify your past experiences into engaging narratives that highlight your analytical prowess and strategic thinking.
✨Tip Number 3
Showcase your financial modelling skills! Be ready to discuss how you've built models from scratch in previous roles. Bring examples to the table that demonstrate your ability to generate meaningful insights and influence decision-making.
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets noticed. Plus, it shows you’re genuinely interested in being part of the Trainline team and ready to take on the challenge of shaping our strategy.
We think you need these skills to ace Head of Strategy
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:We love a structured approach to problem-solving! In your application, give examples of complex problems you've tackled and how you reached clear conclusions. This will show us you can handle the challenges of the role.
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
As a Head of Strategy, you'll need to demonstrate strong analytical and financial modelling skills. Brush up on your financial models and be ready to discuss how you've built them from scratch in the past. Prepare to share specific examples where your insights led to meaningful decisions.
✨Master the Art of Simplification
You'll be presenting complex topics to senior stakeholders, so practice simplifying your ideas without losing depth. Use clear, concise language and consider using visuals to help convey your points. Think about how you can break down intricate strategies into digestible pieces.
✨Showcase Your Collaborative Spirit
This role requires influencing and partnering across teams. Be prepared to discuss instances where you've successfully collaborated with different departments. Highlight your ability to bring diverse perspectives together to shape strategic decisions, especially in a matrixed environment.
✨Prepare for Strategic Questions
Since you'll be leading the annual strategy process, anticipate questions about your approach to strategic planning. Think about how you would set the agenda for key strategic questions and what metrics you'd use to track progress. Show that you can think critically about the future direction of the company.
