Director of Customer Success – Mid-market & Upmarket

About the role

Pleo is seeking a Director of Customer Success to own the strategy and execution for its mid‑market and up‑market customer base. You will shape the operating model, drive retention, and unlock expansion opportunities for large, high‑growth clients.

Key responsibilities

• Define and lead the Customer Success strategy for mid‑market and up‑market segments, prioritising retention and expansion.
• Build, scale and optimise the operating model, including segmentation, engagement motions, success planning and account prioritisation.
• Manage multiple teams of Customer Success Managers and frontline managers, fostering clarity, accountability and a strong coaching culture.
• Collaborate closely with Sales, Support, Onboarding, Product, RevOps, Finance and Marketing to ensure seamless customer journeys.
• Deliver measurable customer and commercial outcomes, reporting on key performance indicators to senior leadership.

Required profile

• Senior leader with proven experience scaling Customer Success organisations, especially through SMB‑to‑enterprise transitions.
• Deep background working with large, high‑growth customers in the technology sector.
• Track record of achieving measurable retention, expansion and revenue results.
• Strong ability to build high‑performing teams and establish customer‑facing operating rhythms.

Required skills