Manager, Digital Scaled Onboarding

About the role

Join Pleo's Customer Experience team as a Manager, Digital Scaled Onboarding. You will lead a Lisbon-based team of Onboarding Managers, guiding a high volume of customers through successful implementation and adoption of Pleo's solutions. This role focuses on evolving a blended onboarding model, combining digital guidance with strategic human interaction to maximize customer value.

Key facts

What you'll do

• Lead a team of digital-first Onboarding Managers responsible for high-volume customer onboarding.
• Manage and refine an onboarding model that is 70% digital and 30% hands-on.
• Develop and implement the scaled onboarding strategy, including customer segmentation and engagement paths.
• Accelerate customer time-to-value by streamlining onboarding processes and achieving key activation milestones.
• Create repeatable digital onboarding processes using automation, webinars, in-product guidance, and self-service content.
• Determine when human intervention is necessary to enhance activation, retention, and customer confidence.
• Drive AI and automation initiatives to boost onboarding efficiency, personalization, and risk detection.
• Monitor onboarding progress and customer signals to identify and address stalled or at-risk customers.
• Design recovery and re-engagement strategies for customers who miss milestones or show early churn risk.
• Establish high standards for onboarding quality across all customer interactions and support.
• Coach and develop Onboarding Managers through regular performance reviews and feedback.
• Build robust operational rhythms, including pipeline reviews, capacity planning, and forecasting.
• Collaborate with Sales to improve pre-sale and post-sale handoffs, ensuring clear documentation of customer needs.
• Partner with Customer Success to ensure smooth onboarding handovers and accurate transfer of customer information.
• Work with Product and Support to identify and resolve recurring onboarding challenges.
• Collaborate with digital content and education teams to enhance onboarding resources.
• Utilize onboarding data to inform decisions, identify trends, and prioritize process improvements.
• Represent scaled onboarding in cross-functional planning to integrate customer needs into company initiatives.

Requirements

• 5+ years of experience in Customer Onboarding, Customer Success, Implementation, Customer Experience, or a similar customer-facing role.
• 2+ years of people-management experience, specifically leading onboarding, implementation, Customer Success, or digitally enabled customer teams.
• Experience developing or managing scaled onboarding models that integrate digital engagement with targeted human support.
• Strong background in SaaS or technology, with an understanding of subscription customer journeys, product adoption, retention, and customer value.
• Experience managing large customer portfolios, emphasizing prioritization, segmentation, automation, and operational discipline.
• Deep understanding of time-to-value, activation, adoption, and onboarding completion metrics.
• Experience designing digital customer journeys using automated outreach, webinars, self-service content, lifecycle triggers, or in-product education.
• Strong leadership and coaching abilities, with a proven track record of improving team performance.
• Experience using customer data and behavioral signals to identify risks, prioritize engagement, and improve onboarding outcomes.
• Strong process improvement skills, capable of identifying friction, simplifying workflows, and building scalable practices.
• Excellent customer communication skills, with the ability to coach others on clear and outcome-focused engagement.
• Strong cross-functional leadership skills, able to align various departments around customer outcomes.
• Commercial and retention awareness, understanding the impact of onboarding on adoption, customer health, and churn.
• Comfortable operating in a fast-paced growth environment, adapting to evolving priorities and balancing strategy with execution.
• Strong analytical and reporting skills, able to translate onboarding data into actionable insights and updates.

Nice to have

• Experience in fintech, payments, spend management, financial technology, or B2B SaaS.
• Experience establishing or scaling a customer onboarding hub in Lisbon.
• Exposure to AI-powered onboarding, conversational AI, automated customer guidance, or predictive customer health solutions.
• Experience with product-led onboarding and digital adoption platforms.
• Familiarity with customer education, learning management systems, webinars, and digital content programs.
• Experience managing multilingual or multi-market customer onboarding.
• Knowledge of finance workflows, accounting processes, ERP integrations, or expense management.
• Experience supporting both small-business and mid-market customer segments.

Skills & tools

CRM, customer success platforms, onboarding tools, learning platforms, support systems, product analytics, workflow automation, AI solutions, business intelligence tools (e.g., Salesforce, Gainsight, Zendesk, Looker, Tableau, Power BI, Jira, Asana, Slack).

Practical notes

Benefits include a Pleo card, catered meals or lunch allowance, comprehensive private healthcare (Vitality, Alan, or Médis), 25 days of holiday plus public holidays, hybrid and fully remote working options, option to purchase 5 additional holiday days, MyndUp access for mental health support, and paid parental leave.