Director, Customer Success

About the role

Pleo is seeking a Director of Customer Success to lead our mid-market and upmarket segments. This is a pivotal, transformational role focused on scaling our customer experience organization. You will build and optimize strategies to ensure customer retention, drive expansion, and maximize long-term value for our growing customer base.

Key facts

What you'll do

• Develop and execute the Customer Success strategy for mid-market and upmarket customers, prioritizing retention and expansion.
• Oversee multiple Customer Success Manager teams and their frontline leaders, fostering a culture of clear communication, accountability, and coaching.
• Design and implement the operational framework for mid-market and upmarket customers, covering segmentation, engagement models, success planning, account prioritization, renewal readiness, and growth initiatives.
• Proactively manage customer risks and enhance visibility into customer health across the portfolio, with a strong focus on preventing churn.
• Collaborate closely with the Sales team on renewals, account strategies, and coordinated customer interactions.
• Create effective success pathways for high-growth customers, balancing scalability with meaningful engagement to ensure rapid value realization.
• Utilize data and portfolio insights to inform decisions regarding team productivity, retention trends, and commercial outcomes.
• Partner with Product, Support, and Operations teams to streamline processes and advocate for customer needs.
• Manage business rhythms for the segment, including forecasts, risk assessments, performance reviews, and executive updates.
• Contribute as a senior leader to the broader Customer Experience strategy at Pleo.

Requirements

• Over 10 years of leadership experience in Customer Success within SaaS, fintech, or technology, with a proven history of strong customer retention.
• Demonstrated ability in people leadership and coaching, including developing frontline managers.
• Experience managing mid-market or upmarket customer portfolios, with sound commercial judgment for prioritizing across a large account base.
• A commercial mindset, capable of connecting customer outcomes to retention, expansion, and long-term account value.
• Data-driven approach, using metrics, forecasts, and portfolio insights to drive accountability.
• Strong executive presence and communication skills, both internally and with customers.
• Comfortable with both strategic planning and hands-on execution.

Nice to have

• Background in fintech, spend management, payments, or financial operations.
• Experience with global or multi-region Customer Experience organizations.
• Track record of improving renewal forecasting, health scoring, and customer operating cadences.
• Familiarity with building segment-specific CX models from the ground up.

Skills & tools

• Customer Success leadership
• People management
• Strategic planning
• Data analysis
• Commercial acumen
• Risk management
• Cross-functional collaboration

Practical notes

• This role does not offer visa sponsorship. Applicants must have a valid right to work in the UK.
• Benefits include a Pleo card, catered lunches or allowance, comprehensive private healthcare (Vitality, Alan, or Médis), 25 days of holiday plus public holidays, hybrid and remote work options, MyndUp access for mental health support, and paid parental leave.
• The interview process includes an intro call, hiring manager interview, peer interview, a take-home challenge with panel presentation, and a final interview with a senior leader.
• Applications should be submitted in English and focus on specific, measurable impacts from previous roles.