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…