About the role
We’re looking for a Director, Customer Success, Large and High 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 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 lead 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 partner closely with cross‑functional teams to ensure customer priorities are understood, customer risk is addressed 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 customers, ensuring the team is focused on customer outcomes, value realisation, retention, expansion, and long‑term relationship strength.
- Lead multiple teams of Customer Success Managers through 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 bar 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 customers.
- 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 looks like at scale for Pleo.
What you bring
- +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 of 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 teams.
- 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 environments.
- 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
You 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.
- 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.
- 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.
