Pleo
Director, Customer Success
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Director, Customer Success
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. Pleo is changing that by building spend solutions that make managing money:
- Seamless
- Empowering
- Surprisingly effective—our vision is to help all businesses ‘go beyond’
The word ‘more than you’d expect’ is where Pleo finds its roots—and this ethos has driven our success for the past 10 years.
About The Role
We’re at a pivotal moment in our journey: every move we make touches 40,000+ customers, our business, and our collective success.
We need bold leaders—people who:
- Uncover unmet customer needs
- Simplify complex problems
- Thoughtfully challenge the status quo
- Aim high and embrace uncertainty as half the story’s fun
We currently comprise 850+ people from over 100 nationalities—collectively determined to shape the future of business spending.
This Role
We are seeking a Director, Customer Success to spearhead our mid-market to upmarket transition at Pleo. This is a transformation role requiring vast people leadership and results-driven execution.
Key Responsibilities
Who You’ll Collaborate With & Report To
You’ll report to our VP of Customer Experience and partner with leaders across:
- Sales
- Support
- Onboarding
- Product
- Revenue Operations (RevOps)
- Finance
- Marketing
You’ll lead multiple Customer Success and frontline leadership teams within the mid-market and upmarket segment.
Core Responsibilities
- Lead Customer Success strategy for mid/upmarket segments:
- Prioritise retention as the foundation
- Use expansion and value growth as catalysts
- Build a scalable operating model for these segments:
- Refine segmentation, customer engagement, and account prioritisation
- Develop deeper value proposition planning and revenue management strategies
- Sustain a proactive risk-assessment culture, focusing on churn prevention through customer health monitoring
- Umsg deeply with Sales teams on renewals, account strategy, and holistic customer engagement
- Optimise success motions for high-growth customers, balancing scale with personalized, value-driven engagement—ensuring swift time to value
- Turn portfolio data insights into actionable decisions for:
- Team productivity
- Retention trends
- Commercial outcomes
- Work cross-functionally with Product, Support, and Operations teams to:
- Reduce customer friction points
- Advocate for customer-centric improvements
- Define business rhythms for the segment:
- Forecasting sessions
- Risk reviews
- Performance assessments
- Executive-level updates
- Invest in Pleo’s broader Customer Experience strategy
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About You: The Must-Haves
You’ll get excited by this opportunity if you have:
- +10+ years leading Customer Success in SaaS, fintech, or tech, with demonstrated expertise in retention and growth
- Strong people leadership and coaching skills, ideal for frontline manager development
- Experience managing large customer portfolios (mid/upmarket), with the ability to assess commercial priorities effectively
- Commercial acumen—clearly linking customer outcomes to retention, account development, and long-term value
- A data-driven mindset, leveraging metrics (health scores, forecasts, churn indicators) to drive holistic success
- Executive clarity and persuasion, both internally and externally with stakeholders
- A balance of strategic slowness and execution hustle—you set direction while rolling up sleeves
What Will Make You Stand Out?
- Industry experience in fintech, spend management, payments, or financial operations
- Exposure to global or multi-region Customer Success environments
- Proven impact around:
- Renewal forecasting or customer health scoring improvements
- Segmented customer operating cadences
- Skills in building tailored, scalable Customer Experience frameworks from the ground up
Fit vs. Misalignment
✅ This Role Aligns With You If:
- You thrive on leading leaders and overseeing scalable success teams
- You get energised by supporting strategic, high-potential accounts
- You balance customer success with commercial imperatives seamlessly
- You add tangibility and process clarity to chaotic operational environments
- You believe in growth through scalable yet human solutions
❌ This Role May Not Be a Fit If:
- You prefer individual contributor roles over managing multiple teams
- You flourish only in stable, low-change environments
- Running teams, customers, commercial outcomes, and strategy simultaneously feels overwhelming
- You’re unfamiliar with executive-level stakeholder conversations
- Your experience excels in high-volume, transactional customer workflows rather than large, strategic accounts
Growth & Impact In Your First Six Months
Our roadmap for you:
- Strengthen scalability and Cust Success models for large, high-potential customers
- Hit key KPIs in retention, engagement readiness, and customer growth
- Demonstrate deep leadership, empowering CS teams and partners across the whole customer lifecycle
- Earn recognition as an inspirer—where Pleo’s most strategic customers feel sustainably empowered
Location
We provide fully remote, hybrid, or in-office structures across available locations, but note:
- You must be legally permitted to work in your chosen country
- Visas will not be sponsored in any listed locations
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Culture, Perks & Rewards
Tangible ways we support you as a Pleo Associate:
- Personal Pleo card—no more reimbursements, just financial freedom
- Personalized cafeteria benefits: Daily lunch catering or fixed allowance
- Private health coverage, tailored to your location (e.g.: Vitality, Alan), and embedded in work practices
- 28 days annual leave + all required public holidays
- Flexible work options: Hybrid / fully remote arrangements backed by growth-minded team norms
- Mental health well-being support, managed through MyndUp (fully accessible to all)
- Parental leave benefits—aligned with local standards
Hiring Journey
Pleo’s interview process is transparent and equity-based:
- Intro Call with a Talent Partner (30 mins): Overview of the role and your application fit
- Hiring Manager Chat (45 mins): Dive into your experience and alignment with key priorities
- Peer Interview (45 mins): Evaluate our culture fit through authentic team matchmaking
- Pleo Challenge and Panel Review (60 mins): Showcasing your problem-solving capabilities through a take-home assignment
- Final Interview with Senior Leadership: Confirm commitment and shared vision
Selection Insights
The most impactful applications we’ve received were crafted with human perspective, showcasing real-world achievements. Here’s why many candidates were overlooked earlier:
- CVs were generic or AI-overwritten, lacking specific results narratives. Presentation matters, details make a difference.
- Tip: Frame results as: “Achieved X (as measured by Y) with Z”
- Bonus: Join your previous employers’ website for further context
- ** üzer ittikre ve misfit i did not carefully rework questions! Answer problem points directly
- Proof of tailored alignment: Highlight nuances that tie you to our unique priorities
Your Application: A Shared Partnership
- Language requirements: Every application must be submitted in English.
- Equity: We ensure human-facilitated, ethical progress with consistent processes.
- Please apply via our platform only (emails/calls can’t be accommodated).
- Diversity is core to Pleo. We’ll see you! Apply and bring your specific story.
- Accessibility and flexibility: Reach out to belonging@pleo.io if you have special interview requirements.
- Transparency on privacy: Personal data flow is governed by our Privacy Policy.
Applying for multiple roles? Alignment matters—confirm why each specific role suits your journey.
Reapplying? Wait 6 months since your last decision before resubmitting.
See you there! 🚀
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