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.
• Build repeatable digital onboarding motions using automated communications, webinars, in-product guidance, self-service content, education programs, and triggered customer journeys.
• Define when human engagement is required and ensure Onboarding Managers intervene at moments where personal guidance can materially improve activation, retention, or customer confidence.
• Drive AI and automation opportunities that improve onboarding efficiency, customer personalisation, risk detection, next-best-action recommendations, and proactive engagement.
• Monitor onboarding health and customer signals to identify stalled, disengaged, at-risk, or complex customers before they fail to complete onboarding.
• Develop customer recovery and re-engagement plays for customers who miss milestones, delay implementation, or show early signs of churn risk.
• Set clear standards for onboarding quality across customer communication, discovery, configuration support, education, expectation-setting, and handover.
• Coach and develop Onboarding Managers through regular one-to-ones, performance reviews, call coaching, development planning, and structured feedback.
• Build strong operating rhythms including pipeline reviews, capacity planning, performance reviews, risk reviews, and onboarding forecast updates.
• Partner with Sales to improve pre-sale and post-sale handoffs, ensuring customer goals, technical requirements, timelines, stakeholders, and commitments are documented clearly.
• Partner with Customer Success to improve onboarding handovers, ensuring success plans, adoption risks, stakeholder information, and outstanding actions transfer accurately.
• Work with Product and Support to identify recurring onboarding friction, including product gaps, technical blockers, knowledge gaps, and avoidable customer contacts.
• Partner with digital content and education teams to improve onboarding guides, webinars, learning paths, tutorials, checklists, and self-service resources.
• Use onboarding data to drive decisions, identify trends, evaluate program effectiveness, and prioritise process improvements.
• Represent scaled onboarding in cross-functional planning, ensuring customer onboarding needs are considered in product launches, process changes, and company initiatives.

To put things into context

In this role, you can expect to work on priorities such as:

• moving customers from purchase to activation faster
• increasing digital onboarding completion and engagement
• reducing manual steps and unnecessary customer meetings
• improving customer education and self-service during onboarding
• identifying stalled or at-risk onboarding customers earlier
• improving the consistency and quality of onboarding delivery
• creating stronger onboarding segmentation and engagement paths
• improving Sales-to-Onboarding and Onboarding-to-Customer-Success handoffs
• introducing AI and automation into onboarding workflows
• increasing the capacity of each Onboarding Manager without reducing customer outcomes
• building a scalable onboarding centre of excellence in Lisbon
• improving the measurement of onboarding success, customer effort, and time-to-value

You can expect to work across a technology environment that includes CRM, customer success platforms, onboarding tools, learning platforms, support systems, product analytics, workflow automation, AI solutions, and business intelligence tools.

Examples may include Salesforce, Gainsight or similar, Zendesk, learning management and webinar platforms, customer engagement tools, product analytics platforms, Looker, Tableau or Power BI, Jira, Asana, and Slack.

What you bring

You’ll thrive in this role if you have:

• 5+ years of experience in Customer Onboarding, Customer Success, Implementation, Customer Experience, or a related customer-facing function.
• 2+ years of people-management experience, ideally leading onboarding, implementation, Customer Success, or digitally enabled customer teams.
• Experience building or managing scaled onboarding models that combine digital engagement with targeted human support.
• Strong SaaS or technology experience with an understanding of subscription customer journeys, product adoption, retention, and customer value.
• Experience leading high-volume customer portfolios where prioritisation, segmentation, automation, and operational discipline are essential.
• A strong 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 people-leadership and coaching skills with a track record of improving individual and team performance.
• Experience using customer data and behavioural signals to identify risk, prioritise engagement, and improve onboarding outcomes.
• Strong process-improvement capability with the ability to identify friction, simplify workflows, and build scalable operating practices.
• Strong customer communication skills with the ability to coach others on clear, confident, and outcome-focused customer engagement.
• Strong cross-functional leadership skills and the ability to align Sales, Customer Success, Support, Product, and Operations around customer outcomes.
• Commercial and retention awareness, with an understanding of how failed or delayed onboarding affects adoption, customer health, revenue, and churn.
• Comfort operating in a fast-paced growth environment where priorities evolve and leaders are expected to move between strategy and execution.
• Strong analytical and reporting skills with the ability to translate onboarding data into decisions, actions, and leadership updates.

Nice to have

• Experience in fintech, payments, spend management, financial technology, or B2B SaaS
• Experience building 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

Why is this role a good fit for you?

This role is a good fit for you if:

• You believe digital onboarding can be scalable without becoming impersonal.
• You understand where automation creates value and where human engagement is still essential.
• You enjoy leading and developing customer-facing teams.
• You are motivated by improving time-to-value, adoption, and customer outcomes.
• You enjoy using data and customer signals to improve journeys and team performance.
• You are comfortable redesigning processes rather than simply maintaining them.
• You know how to balance customer experience, operational efficiency, and business impact.
• You want to build a modern, digital-first onboarding model in a fast-growing technology company.

Show me the benefits

Your own Pleo card (no more out-of-pocket spending!)

Lunch is on us for your work days - enjoy catered meals or receive a lunch allowance based on your local office

Comprehensive private healthcare - depending on your location, coverage options include Vitality, Alan or Médis

We offer 25 days of holiday + your public holidays

For our Team, we offer both hybrid and fully remote working options

Option to purchase 5 additional days of holiday through a salary sacrifice

We use MyndUp to give our employees access to free mental health and well-being support with great success so far

Paid parental leave - we want to make sure that we're supportive of families and help you feel that you don't have to compromise your family due to work

About your application

• English first. Since it's our company language, please submit your application in English. You’ll be using it a lot if you join us.
• A fair look for everyone. Our talent team reads every single application to ensure the process is fair. To keep things running smoothly, we only accept applications through our system—our support team can’t pass on calls or emails.
• Diversity drives us. We can only reach our goals if our team reflects the world around us. That starts with you hitting apply, even if you don't tick every single box. We encourage people from all backgrounds and experiences to join us.
• Interview at your best. We want you to feel comfortable throughout the process. If you have any accessibility requirements or need a specific format, email belonging@pleo.io. We’ll design a process that works for you.
• Your data is safe. When you apply, we process your personal data as a data processor. For more information on how Pleo processes personal data, read our Privacy Policy here.
• Applying for multiple roles? Nothing is stopping you, and we assess every role independently. However, we do look for alignment, so make sure you can explain why your interest and experience are right for each specific role.
• Reapplying. If you’re applying for the same role again, please wait six months from your last decision before hitting submit.