Head of Pricing and Packaging

  • Wayfindi
  • Jan 28, 2026
Full time Manufacturing

Job Description

At Cleo, we're not just building another fintech app. We're embarking on a mission to fundamentally change humanity's relationship with money. Imagine a world where everyone, regardless of background or income, has access to a hyper-intelligent financial advisor in their pocket. That's the future we're creating.

Cleo is a rare success story: a profitable, fast-growing unicorn with over $200 million in ARR and growing over 2x year-over-year. This isn't just a job; it's a chance to join a team of brilliant, driven individuals who are passionate about making a real difference. We have an exceptionally high bar for talent, seeking individuals who are not only at the top of their field but also embody our culture of collaboration and positive impact.

If you're driven by complex challenges that push your expertise, the chance to shape something truly transformative, and the potential to share in Cleo's success as we scale, while growing alongside a company that's scaling fast, this might be your perfect fit.

We're hiring a Head of Pricing & Packaging to own how our subscription offering and monetisation strategy can evolve: how features are bundled, priced, and positioned to drive sustainable growth in paid subscribers and revenue.

This is a highly commercial and analytical role. You will translate insight, data, and business strategy into tangible subscription propositions that users understand, value, and pay for.

  • You'll be hands-on in the data while also setting the long-term direction for how our monetisation strategy and proposition function evolves.
Key Responsibilities
  • Own Pricing & Packaging Strategy:
  • Lead the end-to-end strategy for subscription pricing and tier packaging, ensuring our subscription offering is competitive, distinctive, and commercially sound across markets
  • Define how existing and new features are bundled into clear, differentiated subscription tiers
  • Stay on top of cross-company product roadmap to optimise our monetisation and subscription model.
  • Decision making and Cross-Functional Leadership:
  • Collaborate closely with Product, Commercial, Lending, and Analytics to scope, prioritise, and run pricing and packaging experiments
  • Work with Commercial, Marketing, and Compliance teams to ensure propositions are clear, coherent, compliant, and scalable
  • Translate experiment results into clear go / no-go decisions by truly understanding short and long-term impact
  • Build feature-level P&Ls and business cases to assess ROI and trade-offs together with our commercial team
  • Analyse conversion, retention, ARPU, and LTV to inform pricing and bundling decisions
  • Independently run analysis using Excel / spreadsheets (hands-on expected)
  • Partner with Commercial and Finance and other pillars to align pricing strategy with forecasting, targets, and long-term revenue plans
  • Translate Insight into Propositions:
  • Work closely with User Research to understand perceived value, willingness-to-pay, and unmet needs. Run pricing and WTP research independently if needed.
  • Partner with Product Analysts to synthesise behavioural data and performance insights
  • Turn qualitative and quantitative insight into concrete pricing and packaging recommendations
  • Build & Scale the Function:
  • Hire and develop a team as our subscription strategy matures
  • Define experimentation frameworks, decision principles, and commercial guardrails
  • Act as the internal authority on subscription monetisation and proposition design
What We're Looking For
  • 6-10+ years of experience in pricing, packaging, monetisation, commercial strategy, revenue ops, or product marketing
  • Strong commercial and financial acumen, with experience analysing feature-level economics and track record of growing revenue
  • Comfortable being hands-on in Excel - building models, scenarios, and business cases yourself
  • Deep understanding of consumer subscription businesses
  • Strong product sense and intuition for value proposition design
  • Experience working inside or alongside product squads running experiments
  • Confident influencing senior stakeholders
  • Knowledge of the US financial market (consumer behaviour, regulation, pricing norms) preferred
What do you get for all your hard work?
  • A competitive compensation package (base + equity) with bi-annual reviews, aligned to our quarterly OKR planning cycles. You can view our public progression framework and salary bandings here:
  • Work at one of the fastest-growing tech startups, backed by top VC firms, Balderton & EQT Ventures
  • A clear progression plan. We want you to keep growing. That means trying new things, leading others, challenging the status quo and owning your impact. Always with our complete support.
  • Flexibility. We can't fight for the world's financial health if we're not healthy ourselves. We work with everyone to make sure they have the balance they need to do their best work
  • Work where you work best. We're a globally distributed team. If you live in London we have a hybrid approach, we'd love you to spend one day a week or more in our beautiful office. If you're outside of London, we'll encourage you to spend a couple of days with us a few times per year. And we'll cover your travel costs, naturally.
Other Benefits
  • Company-wide performance reviews every 6 months
  • Generous pay increases for high-performing team members
  • Equity top-ups for team members getting promoted
  • 25 days annual leave a year + public holidays (+ an additional day for every year you spend at Cleo, up to 30 days)
  • 6% employer-matched pension in the UK
  • Private Medical Insurance via Vitality, dental cover, and life assurance
  • Enhanced parental leave
  • 1 month paid sabbatical after 4 years at Cleo
  • Regular socials and activities, online and in-person
  • We'll pay for your OpenAI subscription
  • Online mental health support via Spill
  • Workplace Nursery Scheme
  • And many more!
Welcoming Everyone

We strongly encourage applications from people of colour, the LGBTQ+ community, people with disabilities, neurodivergent people, parents, carers, and people from lower socio-economic backgrounds.

If there's anything we can do to accommodate your specific situation, please let us know.

Download the Test Flight

App access for people in the UK & Europe:If you are an iOS user, please use this link to sign up to ourTestFlightversion of the app, so you can have a play around with the functionality and features:

By submitting this application, I confirm that all the information given by me in this application for employment and any additional documents attached hereto are true to the best of my knowledge and that I have not wilfully suppressed any material fact. I confirm I have disclosed if applicable any previous employment with Cleo AI. I accept that if any of the information given by me in this application is in any way false or incorrect, my application may be rejected, any offer of employment may be withdrawn or my employment with Cleo AI may be terminated summarily or I may be dismissed. By submitting this application, I agree that my personal data will be processed in accordance with Cleo AI's Candidate Privacy Notice