OverviewAbout Pleo. Messy spend management is tricky business. 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. 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 RoleWe '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 Rev Ops 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 ToYou 'll report to our VP of Customer Experience and work closely with leaders across Sales, Support, Onboarding, Product, Rev Ops, 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 DoingLead 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 leverLead multiple teams through frontline managers, creating clarity, accountability, and a strong coaching cultureBuild and scale the operating model for mid-market and upmarket customers: segmentation, engagement motions, success planning, account prioritisation, renewal readiness and growth playsDrive proactive risk management and customer health visibility across the portfolio, with a particular emphasis on churn preventionPartner closely with Sales on renewals,



account strategy, and coordinated customer engagementCreate stronger success motions for high-growth customers that balance scale with meaningful engagement and ensure customers are positioned to realise value quicklyUse data and portfolio insight to drive decisions on team productivity, retention trends, and commercial outcomesPartner cross-functionally with Product, Support, and Operations to reduce friction and advocate for customer needsOwn business rhythms for the segment: forecasts, risk reviews, performance reviews, and executive updatesContribute to Pleo 's broader Customer Experience strategy as a senior leaderWhat You BringYou’ll thrive in this role if you have:+10 years of experience in Customer Success leadership in Saa S, fintech, or technology, with a demonstrable track record in customer retentionStrong people leadership and coaching capability, including development of frontline managersExperience managing portfolios at mid-market or upmarket scale, with the commercial judgement to prioritise appropriately across a large account baseCommercial mindset with clear ability to connect customer outcomes to retention, expansion, and long-term account valueData-driven approach with experience using metrics, forecasts, and portfolio insights to drive accountabilityExecutive presence and communication skills, both internally and with customersComfort operating across strategy and execution, you set direction and you roll up your sleevesWhat Will Set You ApartExperience in fintech, spend management, payments, or financial operationsExposure to general or multi-region CX organisationsExperience improving renewal forecasting, health scoring, and customer operating cadencesFamiliarity with building segment-specific CX models from the ground upWhy Is This Role a Good Fit for YouThis role is a good fit for you if:You enjoy leading leaders and building strong, scalable Customer Success organisationsYou are energised by working with large, strategic, and high-growth customersYou know how to balance customer outcomes,



team development, and commercial performanceYou like building structure and clarity in fast-moving environmentsYou want to shape how Customer Success scales in a company that is continuing to growHow You’ll Develop In This RoleIn your first 6 months at Pleo, you’ll:Establish a stronger and more scalable Customer Success model for large and high-growth customersDeliver measurable gains in retention, customer health, renewal execution, and growth supportBuild a stronger bench of Customer Success leadership and team capability across the organisationBe recognised as a key leader in how Pleo supports, retains and grows its most important customersThe LocationPlease 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 - catered meals or lunch allowance based on your local officeComprehensive private healthcare - coverage options include Vitality, Alan or Médis25 days of holiday + public holidaysHybrid and fully remote working optionsAccess to free mental health and well-being supportPaid parental leaveThe Interview ProcessWe 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:Intro call: A 30-minute chat with our Talent Partner to discuss the role and your backgroundHiring Manager Interview: 45 mins with the Hiring Manager on your experience and fitPeer Interview: 45 minutes with potential future colleagues to assess cultural addPleo Challenge and Panel Interview: Take-home test and 60-minute team interviewFinal Interview: With a Senior LeaderAbout Your ApplicationEnglish first. Submit your application in EnglishA fair look for everyone. Applications are reviewed manuallyDiversity drives us. We encourage applicants from all backgroundsInterview accessibility: email belonging@ for accommodationsYour data is safe. Privacy policy explains how we process personal dataApplying for multiple roles: roles are assessed independentlyReapplying: wait six months from your last decision before submitting

📌 Director, Customer Success (Madrid)
🏢 Pleo
📍 Madrid