Senior Manager, Onboarding

About the role

Pleo seeks a Senior Manager, Onboarding to guide the strategy and operations for integrating its largest and most complex customers. This role ensures enterprise clients successfully transition from contract signing to full implementation, adoption, and measurable value through a structured, relationship-focused onboarding journey. You will lead a team managing intricate customer programs that may span multiple business units, countries, technical integrations, senior stakeholders, and change management needs.

Key facts

What you'll do

• Define and implement the onboarding strategy for Pleo's most significant customers, leading the team responsible for its execution.
• Manage and develop a team of four Enterprise Onboarding and Enablement Managers, setting clear objectives for customer outcomes, quality, and time-to-value.
• Oversee the complete onboarding process, from initial discovery and planning through configuration, integrations, enablement, launch, and smooth handover to Customer Success.
• Cultivate trust with high-level stakeholders, including CFOs, finance leaders, transformation leads, IT leaders, and executive sponsors.
• Maintain a focus on business value in all onboarding discussions, connecting Pleo's capabilities to the customer's strategic goals.
• Lead executive discussions on program progress, value, risks, and readiness, while also engaging in technical conversations with Product, Engineering, Solutions, and Security teams.
• Establish clear governance for each program, defining scope, milestones, owners, decisions, dependencies, and risks.
• Organize regular steering calls and reviews for critical programs.
• Identify and address risks early, such as stalled decisions, low engagement, technical blockers, or stakeholder changes, and develop recovery plans with clear actions and timelines.
• Collaborate with Sales before and during handover to confirm requirements, complexity, and commitments.
• Partner with Product and Engineering to resolve integration issues, technical challenges, and customer-specific implementation risks.
• Ensure a strong handover to Customer Success, transferring goals, relationships, risks, and open items effectively.
• Design enablement programs that help administrators, finance teams, managers, and employees effectively use Pleo.
• Customize enablement approaches for different user groups, recognizing varied needs.
• Support customers in managing change, preparing users, fostering champions, and embedding new workflows.
• Monitor onboarding health, timelines, capacity, and go-live confidence, and forecast upcoming needs.
• Use insights to refine the onboarding model, identify patterns, and reduce unnecessary complexity.
• Act as the voice of the enterprise customer within Pleo, ensuring recurring blockers and product friction are communicated to Product, Engineering, and leadership.
• Continuously elevate the standard of support for Pleo's most complex customers, from initial contact to realized value.

Requirements

• 8+ years of experience in customer onboarding, enterprise implementation, customer success, customer enablement, or a similar customer-facing role.
• 4+ years of experience leading teams, preferably in enterprise onboarding, implementation, solutions, or customer success.
• Proven track record of successfully delivering onboarding or implementation programs at enterprise technology companies.
• Experience working with large, complex customers involving multiple stakeholders, regions, entities, workflows, or technical dependencies.
• A leadership style that prioritizes relationships and quickly builds trust with senior customer stakeholders.
• Strong executive presence, comfortable presenting to CFOs, finance leaders, technology leaders, and executive sponsors.
• Experience leading technical discussions with Product teams regarding integrations, security, data, or configuration.
• Experience developing enablement programs tailored for diverse audiences.
• Strong people management and coaching abilities, with a history of building high-performing, customer-facing teams.
• Commercial awareness, understanding the impact of onboarding quality on adoption, retention, customer confidence, revenue, and account growth.
• Strong cross-functional leadership skills, capable of influencing teams and leaders without direct authority.
• A data-driven and disciplined approach, using metrics, forecasts, and customer signals to inform decisions.
• Adaptability to a rapidly growing environment.

Practical notes

This role offers a hybrid work setup in Lisbon. Candidates must be physically based in the country of their choice with valid right to work; visa sponsorship is not available. Benefits include a Pleo card, catered lunches or allowance, comprehensive private healthcare (Vitality, Alan, or Médis), 25 days of holiday plus public holidays, MyndUp access for mental health support, and paid parental leave. The interview process includes an intro call, a hiring manager interview, a take-home challenge with a panel interview, and a final interview with a senior leader. Applications must be submitted in English through the system.