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

In this role, you'll lead multiple teams of Customer Success Managers, develop frontline leaders, and work hands-in-hand with Sales, Product, Support, and RevOps to drive retention, expansion, and long-term customer value.

This role is ideal for someone who has scaled a CX org through a similar SMB to enterprise transition, and who is genuinely energised by the challenge of building, not just running.

Who you’ll be working with and reporting to

You'll report to our VP of Customer Experience and work closely with leaders across Sales, Support, Onboarding, Product, RevOps, Finance and 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 a Director, Customer Success, you will:

• Lead the Customer Success strategy for Pleo's mid-market and upmarket segment, with a clear focus on 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 mid-market and upmarket customers: segmentation, engagement motions, success planning, account prioritisation, renewal readiness and 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 that balance scale with meaningful engagement and ensure customers are positioned to realise value quickly
• Use data and portfolio insight to drive decisions on team productivity, retention trends, and commercial outcomes
• Partner cross-functionally with Product, Support, and Operations to reduce friction and advocate for customer needs
• Own business rhythms for the segment: forecasts, risk reviews, performance reviews, and executive updates
• Contribute to Pleo's broader Customer Experience strategy as a senior leader

What you bring

You’ll thrive in this role if you have:

• +10 years of experience in Customer Success leadership in SaaS, fintech, or technology, with a demonstrable track record in customer retention
• Strong people leadership and coaching capability, including 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
• Commercial mindset with clear ability to connect customer outcomes to retention, expansion, and long-term account value
• Data-driven approach with experience using metrics, forecasts, and portfolio insights to drive accountability
• Executive presence and communication skills, both internally and with customers
• Comfort operating across strategy and execution, you set direction and you roll 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
• Experience improving renewal forecasting, health scoring, and 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 a good fit for you if:

• You enjoy leading leaders and building strong, scalable Customer Success organisations
• You are energised by working with large, strategic, and high-growth customers
• You know how to balance customer outcomes, team development, and commercial performance
• You like building structure and clarity in fast-moving environements
• You want to shape how Customer Success scales in a company that is continuing to grow

This role is not a good fit for you if:

• You prefer an individual contributor role rather than leading multiple teams
• You are most comfortable in highly stable environments with limited change
• You do not enjoy balancing strategy, people leadership, customer engagement, and operational accountability
• You are uncomfortable with executive-level customer interaction and complex commercial conversations

• You prefer small-account, high-volume success models over strategic and high-growth customer leadership

How you’ll develop in this role

In your first 6 months at Pleo, you’ll:

• Establish a stronger and more scalable Customer Success model for large and high-growth customers

• Deliver measurable gains in retention customer health, renewal execution, and growth support
• Build a stronger bench of Customer Success leadership and team capability across the organisation
• Be recognised as a key leader in how Pleo supports, retains and grows its most important customers

The location

Please note: We can hire on a remote, hybrid or in-person set-up in any of the locations listed on the advert but you will need to be physically based in the country of your choice with a valid right to work. We are unable to offer visa sponsorship for this role in any of the listed locations.

Show me the benefits!

• Your own Pleo card (no more out-of-pocket spending!)
• Lunch is on us for your work days - enjoy catered meals or receive a lunch allowance based on your local office
• Comprehensive private healthcare - depending on your location, coverage options include Vitality, Alan or Médis
• We offer 25 days of holiday + your public holidays
• For our Team, we offer both hybrid and fully remote working options
• We use MyndUp to give our employees access to free mental health and well-being support with great success so far
• Paid parental leave - we want to make sure that we're supportive of families and help you feel that you don't have to compromise your family due to work

The interview process

We want to ensure you are set-up for success and understand what will be expected of you. If your application is successful, our interview process is as follows:

1. Intro call: A 30-minute chat with our Talent Partner to discuss the role and your background.
2. Hiring Manager Interview: 45 mins interview with the Hiring Manager to go deeper on your experience and how your profile can fit to the role
3. Peer Interview: 45 minute interview with potential future colleagues, it's designed to assess cultural add
4. Pleo Challenge and Panel Interview: We will send you a take home test and invite you to present it during a 60 mins team interview. This is an opportunity to show us how you would handle the day to day of the role
5. Final Interview: A final interview with a Senior Leader

Transparency is important to us so we also wanted to share some insights about what we’re looking for in applications to ensure you can set yourself up for success!

Last time we hired a similar role, we received a vast number of applications but only a few were selected for an intro call. Some of the key reasons why previous candidates didn’t make it past the application screening stage include:

• CV writing and content: we receive a lot of CVs, and many of them are AI-generated. We love seeing people leverage AI—it’s a big focus for us internally too—but without human intervention, these CVs can sometimes become generic and fail to show a candidate in the best light. What we're really looking for is the specific details of real impact that only you know from your previous experience. A top tip from us is to use the “Achieved X, as measured by Y, by doing Z” formula (credit: Laszlo Bock, ~2014) to give a really clear picture of what you’ve worked on. A final note: including links to your previous companies' websites is a huge help and allows us to truly understand your background!
• Application care: every single application we receive is reviewed by a human (yes, hundreds of them) because we believe that candidates' efforts should be matched by an equal level of human care. This means that we expect a similar level of attention put into your application. Read and answer the application questions carefully, they make a huge difference in our decision-making process.
• Profile to role fit: highlight most important aspects of the role, points that might get misunderstood, any specific industry requirements etc.

About your application

• English first. Since it's our company language, please submit your application in English. You’ll be using it a lot if you join us.
• A fair look for everyone. Our talent team reads every single application to ensure the process is fair. To keep things running smoothly, we only accept applications through our system—our support team can’t pass on calls or emails.
• Diversity drives us. We can only reach our goals if our team reflects the world around us. That starts with you hitting apply, even if you don't tick every single box. We encourage people from all backgrounds and experiences to join us.
• Interview at your best. We want you to feel comfortable throughout the process. If you have any accessibility requirements or need a specific format, email belonging@pleo.io. We’ll design a process that works for you.
• Your data is safe. When you apply, we process your personal data as a data processor. For more information on how Pleo processes personal data, read our Privacy Policy here.
• Applying for multiple roles? Nothing is stopping you, and we assess every role independently. However, we do look for alignment, so make sure you can explain why your interest and experience are right for each specific role.
• Reapplying. If you’re applying for the same role again, please wait six months from your last decision before hitting submit.