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Director, Customer Success
About Pleo
Messy spend management is tricky business. And tedious processes are a lose-lose situation for all involved, not just finance. At Pleo, we're changing that. We build spend solutions that make managing money seamless, empowering, and surprisingly effective for finance teams and employees alike—with a vision to help all businesses ‘go beyond.’
The word ‘Pleo’ actually means ‘more than you’d expect’, and living by that mantra has been the secret to our success over the last 10 years.
Now, we’re at a pivotal moment in our journey; every move we make has a direct impact on our 40,000+ customers, our business, and our collective success. We need people who take pride in uncovering customer needs, who turn complex problems into simple solutions, challenge the way things are done (respectfully), and always aim high. With great ambitions driving us forward, we can’t say we’ve got this whole thing figured out. And frankly, that’s half the fun! What we can say is that we’re a driven, progressive, and—importantly—a kind bunch of 850+ people from over 100 nationalities, all committed to delivering the future of business spending, together.
About The Role
We’re looking for a Director, Customer Success, to lead our mid-market and upmarket segments at Pleo. This is a transformation role.
Who You’ll Work With & Report To
You’ll report to our VP of Customer Experience and work closely with leaders:
- Sales
- Support
- Onboarding
- Product
- RevOps
- Finance
- Marketing
You’ll lead multiple teams of Customer Success Managers and frontline people leaders across the mid-market and upmarket segment.
What You’ll Be Doing
As Director, Customer Success, you will:
- Lead the Customer Success strategy for Pleo’s mid-market and upmarket segment, with retention as the foundation and expansion as the growth lever.
- Lead multiple teams through frontline managers, creating clarity, accountability, and a strong coaching culture.
- Build and scale the operating model for mid-market and upmarket customers:
- Segmentation & engagement motions
- Success planning
- Account prioritisation
- Renewal readiness
- Growth plays
- Drive proactive risk management and customer health visibility across the portfolio, with a particular emphasis on churn prevention.
- Partner closely with Sales on renewals, account strategy, and coordinated customer engagement.
- Create stronger success motions for high-growth customers, ensuring:
- Balance of scale & meaningful engagement
- Customers positioned to realise value quickly.
- Use data & portfolio insight to drive decisions on:
- Team productivity
- Retention trends
- Commercial outcomes.
- Partner cross-functionally with Product, Support, and Operations to:
- Reduce friction
- Advocate for customer needs.
- Own business rhythms for the segment:
- Forecasts
- Risk reviews
- Performance reviews
- Executive updates.
- Contribute to Pleo’s broader Customer Experience strategy as a senior leader.
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What You Bring
You’ll thrive in this role if you have:
✅ +10 years of experience in Customer Success leadership in:
- SaaS
- Fintech
- Technology
- A demonstrable track record in customer retention.
✅ Strong:
- People leadership & coaching skills
- Development of frontline managers.
✅ Experience managing portfolios at mid-market or upmarket scale, with the commercial judgement to:
- Prioritise appropriately across a large account base.
✅ A commercial mindset, with the ability to:
- Connectcustomer outcomes to retention, expansion & long-term account value.
✅ A data-driven approach, including:
- Using metrics, forecasts & portfolio insights to drive accountability.
✅ Executive presence & communication skills, both internally and with customers.
✅ Comfort operating across strategy & execution, setting direction and rolling up your sleeves.
What will set you apart:
- Experience in fintech, spend management, payments, or financial operations.
- Exposure to global or multi-region CX organisations.
- Improving renewal forecasting, health scoring & customer operating cadences.
- Familiarity with building segment-specific CX models from the ground up.
Why Is This Role a Good Fit for You?
This role is right for you if:
- You enjoy leading leaders and building strong, scalable Customer Success organisations.
- You’re energised by working with large, strategic, and high-growth customers.
- You know how to balance customer outcomes, team development, & commercial performance.
- You like building structure & clarity in fast-moving environments.
- You want to shape how Customer Success scales in a company that’s still growing.
This role is not a good fit if:
- You prefer an individual contributor role rather than leading multiple teams.
- You’re most comfortable in highly stable environments with limited change.
- You don’t enjoy balancing strategy, people leadership, customer engagement & operational accountability.
- You’re uncomfortable with executive-level customer interaction & complex commercial conversations.
- You prefer small-account, high-volume models over strategic & high-growth customer leadership.
How You’ll Develop In This Role
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Within your first 6 months at Pleo, you’ll:
- Establish a stronger, more scalable Customer Success model for large and high-growth customers.
- Deliver measurable gains in:
- Retention
- Customer health
- Renewal execution
- Growth support.
- Build a stronger bench of Customer Success leadership & team capability across the organisation.
- Be recognised as a key leader in how Pleo supports, retains & grows its most important customers.
Location Flexibility
We can hire on remote, hybrid, or in-person—just your location (any of the listed countries) and valid right to work. We cannot sponsor visas.
The Benefits
💳 Your own Pleo card (no more out-of-pocket spending!) 🍽️ Lunch on us (catered or lunch allowance in your local office). 🏥 Comprehensive private healthcare (Vitality, Alan, or Médis, depending on location). 📅 25 days holiday + all public holidays. 🏠 Hybrid & remote options for our team. 🧠 MyndUp access (free mental health & wellbeing support). 👶 Paid parental leave—we believe in work-life balance.
Interview Process
- Intro Call (30 mins with a Talent Partner).
- Hiring Manager Interview (45 mins).
- Peer Interview (45 mins to assess cultural fit).
- Pleo Challenge + Panel Interview (take-home test, 60 mins).
- Final Interview (with a Senior Leader).
Key Insights on Applications
🔹 Our last similar hire saw hundreds of applications, but only a few progressed to the intro call. Reasons previous candidates were screened out:
📄 CV Quality:
- Many applications were AI-generated—human review is essential.
- Why? AI can lack nuance. Focus on real-world impact using the formula: “Achieved X, as measured by Y, by doing Z.”
📝 Careful Application Writing:
- Every application is reviewed by humans, so thoroughness and attention matter.
- Always answer questions fully—poor effort hurts your chances.
🔍 Profile to Role Fit:
- Highlight key role aspects and industry requirements.
About Your Application
🌍 English only—it’s our company language. 🔒 Applications go through our system only (no external calls/emails). 🌟 Diversity matters—beyond ticking boxes, lives are transformed when varied teams succeed.
🤝 Accessibility: If you need adjustments, reply to belonging@pleo.io. 📡 Data privacy: Your info is processed securely. Review our Privacy Policy. 🔄 Multiple roles? Apply independently—we look for role-specific alignment. ⏳ Reapplying? Wait 6 months from the last decision.
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