Manager, Digital Scaled Onboarding

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 Manager, Digital Scaled Onboarding to join our Customer Experience organisation at Pleo. In this role, you’ll lead a Lisbon-based team of digital-first Onboarding Managers responsible for helping high volumes of customers successfully implement, adopt, and begin realising value from Pleo. You’ll own and evolve an onboarding model that is approximately 70% digital and 30% hands-on. The goal is not to remove human engagement—it is to use it intentionally. Customers should receive scalable digital guidance for repeatable onboarding needs, while getting targeted human support when complexity, risk, customer value, or adoption signals require it. This role is ideal for a customer onboarding leader who understands how to combine people, process, content, data, automation, and AI to create a faster and more consistent path to value. You’ll be responsible for improving the onboarding journey, developing the team, increasing digital engagement, and ensuring customers transition into Customer Success with strong adoption and clear next steps. You should bring experience leading customer-facing teams in a SaaS or technology environment, along with a strong understanding of digital onboarding, customer lifecycle management, and scaled engagement models. WHO YOU’LL BE WORKING WITH AND REPORTING TO You’ll report to our Director of Scaled Customer Success and Onboarding and work closely with teams across: - Customer Success - Customer Support - Digital Content and Self-Service - Product and Product Operations - Sales and Revenue Operations - Implementation and Solutions teams - Data and Analytics - Program Management and Operations You’ll directly lead a team of digital-first Onboarding Managers, setting clear expectations for customer outcomes, digital engagement, productivity, quality, and operational execution. You’ll also partner across the customer journey to ensure onboarding commitments are clear, customer information is transferred accurately, risks are identified early, and customers move into their ongoing success motion with a strong foundation. WHAT YOU’LL BE DOING As a Manager, Digital Scaled Onboarding, you will: - Lead a team of digital-first Onboarding Managers responsible for managing high-volume customer onboarding through a blend of digital and human engagement. - Own the 70% digital and 30% hands-on onboarding model, ensuring customers receive the right type of support based on complexity, value, risk, behaviour, and lifecycle stage. - Define and evolve the scaled onboarding strategy, including customer segmentation, engagement paths, digital journeys, intervention points, and escalation criteria. - Improve time-to-value by simplifying onboarding steps, removing friction, and helping customers reach key activation and adoption milestones faster. - B…