Director, Customer Success (Large & High Growth)

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, Large and Hight Growth to join our Customer Experience team at Pleo. In this role, you'll lead the Customer Success strategy, operating model, and team performance for a portfolio of large, high-growth customers. You'll be responsible for building and leading multiple teams of Customer Success Managers focused on driving customer outcomes, retention, expansion, and long-term strategic value.

This role is ideal for a Senior Customer Success leader who knows how to scale high-performing teams, build strong customer - facing operating rhythms, and lead in a fast-paced, growth environment. You should bring deep experience working with a large customers, a strong background in the technology vertical, and a proven track record of delivering measurable customer and commercial results.

You will play a critical leadership role in how Pleo supports strategic and growth-stage customers- ensuring we deepen relationships, accelerate time-to-value, proactively manage risk, and create strong alignment across Customer Success, Support, Product, Sales and the broader business

WHO YOU’LL BE WORKING WITH AND REPORTING TO

You'll report to our VP of Customer Experience and work closely with leaders across Customer Support, Onboarding, Program Management and Operations, Product, Sales, RevOps, Finance and Marketing.

You'll led multiple teams of Customer Success Managers and frontline people leaders, creating strong execution, consistency, and accountability across the large and high-growth customer segment. You'll also partner closely with cross-functional teams to ensure customer priorities are understood, customer risk is addresses early, and the overall customer experience supports both retention and growth.

WHAT YOU’LL BE DOING

As a Director, Customer Success, you will:

• Lead the Customer Success strategy for large and high-growth customer, ensuring the team is focused on customer outcomes, value realisation, retention, expansion, and long-term relationship strength

• Lead multiple teams of Customer Success Managers though frontline managers or team leads, creating clarity, accountability, strong coaching, and consistent performance

• Build and scale the operating model for managing large and high-growth customers, including segmentation, engagement motions, success planning, account prioritisation, renewal readiness, and growth plays

• Drive customer health, retention, and expansion performance by building proactive risk management, better visibility into account health, and stronger execution across the customer lifecycle

• Partner closely with Sales and Account teams to ensure smooth transitions, aligned account strategy, and coordinated customer engagement across renewals and growth opportunities

• 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 operational insight to drive decisions across customer health, portfolio performance, team productivity, retention trends, and commercial outcomes

• Partner cross-functionally with Product, Support, and Operations to address recurring friction, improve customer experience and advocate for the needs of strategic customers

• Strengthen talent, leadership capability, and team development across the Customer Success organisation by raising the bard on coaching, execution discipline, and customer-centric leadership

• Own business rhythms and reporting for the segment, including forecasts, risk reviews, performance reviews, executive updates, and action planning

• Contribute to broader Customer Experience strategy as a senior leader, helping shape how Pleo scales service, success, and customer outcomes across the business

To put things into context, in this role, you can expect to work on priorities such as:

• Improving retention and expansion performance across large and high-growth customer

• Strengthening customer health visibility and proactive engagement

• Building scalable success motions for strategic and growth-stage accounts

• Improving executive engagement and relationship management

• Reducing churn risk through earlier intervention and stronger account planning

• Improving renewal readiness and commercial coordination with Sales

• Strengthening customer success leadership capability across multiple teams

• Improving cross-functional alignment between Customer Success, Support, Product, and Sales

• Creating more consistency in how large customers are managed across lifecycle stages

• Helping define what great Customer Success look like at scale for Pleo

WHAT YOU BRING

You’ll thrive in this role if you have:

• +10 years of experience in Customer Success leadership with a proven track record of leading teams in SaaS, fintech, or technology environments

• Strong experience leading multiple teams of Customer Success Managers, including direct management of people leaders and/or larger team structures

• A strong background in technology vertical, with a clear understanding of how to support complex customers in fast-moving, product-led or service-enabled environments

• Proven results in fast-paced, high-growth environments where scale, prioritisation, and cross-functional execution are critical

• Proven success working with large customers including strategic accounts, complex stakeholders, executive relationships, renewals, and growth motions

• A strong commercial mindset with the ability to connect customer outcomes to retention, expansion, and long-term account value

• Deep understanding customer health, lifecycle management, success planning, and risk mitigation

• Strong leadership and coaching capability with a track record of developing managers and building high-performing Customer Success team

• Strong cross-functional leadership skills and the ability to align effectively with Sales, Product, Support, RevOps, and Operations

• A data-driven approach with experience using metrics, forecasts, and portfolio insights to drive action and accountability

• Strong executive presence and communication skills with the ability to influence internally and externally at senior levels

• Comfort operating at both strategic and execution levels, moving from high-level direction into practical operating improvements when needed

Nice to have:

• Experience in fintech, spend management, payments, or financial operations

• Experience building or scaling segment-specific Customer Success models

• Familiarity with enterprise and mid market growth accounts motions

• Experience improving renewal forecasting, health scoring, playbooks, or customer operating cadences

• Exposure to global or multi-region customer success organisations

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 https://www.pleo.io/en/legal.

• 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.