Senior Manager, Onboarding (high-touch customers)

About this role

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 Senior Manager, Onboarding to join our Customer Experience team at Pleo!. In this role, you'll lead the strategy, operating model, and team responsible for onboarding Pleo's largest, most complex, and strategically important customers.

You'll ensure enterprise customers move from contract signature to successful implementation, adoption, and measurable value through a structured, relationship-driven onboarding experience. You'll lead a team responsible for complex customer program that may involve multiple business units, entities, countries, technical integrations, senior stakeholders and change-management requirements

WHO YOU’LL BE WORKING WITH AND REPORTING TO

You'll report to our Director, Customer Success and work closely with leaders and team across customer success and support, sales and account management, product, and others.

You'll lead a team of 4 enterprise onboarding managers responsible for delivering high-touch onboarding programs to Pleo's largest customers.

WHAT YOU’LL BE DOING

As a Senior Manager, Onboarding you will:

Lead the team and the strategy:

- Set the strategy for onboarding our biggest, most complex customers, and lead the team that delivers it.

- Manage and grow a team of Enterprise Onboarding and Enablement Managers. Give them clear goals around customer outcomes, quality, and time-to-value.

- Run the end-to-end onboarding model: from discovery and implementation planning through configuration, integrations, enablement, go-live, and handover to Customer Success.

Build relationships that matter:

- Build trust with senior stakeholders, CFOs, finance leaders, transformation leads, IT leaders, and executive sponsors.

- Keep every onboarding conversation focused on business value, not just technical delivery. Connect what Pleo does to what the customer is actually trying to achieve.

- Lead executive conversations on progress, value, risk, and readiness, and hold your own in technical conversations with Product, Engineering, Solutions, and Security, without losing the bigger picture.

Keep programmes on track:

- Set clear governance for every programme: scope, milestones, owners, decisions, dependencies, and risks.

- Build a steady rhythm of steering calls and reviews for the programmes that matter most.

- Spot risk early, stalled decisions, low engagement, technical blockers, changed stakeholders, and lead recovery plans when a programme needs one, with clear actions, owners, and timelines.

Strengthen the handoffs:

- Work with Sales before and during handover to confirm requirements, complexity, timelines, and what we've committed to, so nothing gets lost in translation.

- Work with Product and Engineering to unblock integrations, technical issues, and customer-specific implementation risks.

- Build a strong handover to Customer Success, so goals, relationships, risks, and open items carry over cleanly.

Drive adoption, not just go-live:

- Build enablement programmes that help admins, finance teams, managers, and employees actually use Pleo well.

- Tailor how you enable different people, a finance admin needs something different from an employee submitting expenses.

- Help customers manage the change: preparing users, building champions, and making new ways of working stick.

Use data to keep improving:

- Track onboarding health, timelines, capacity, and go-live confidence, and forecast what's coming.

- Use what you learn to improve the model, spot patterns, and cut out unnecessary complexity.

- Be the voice of the enterprise customer inside Pleo, make sure recurring blockers and product friction get seen by Product, Engineering, and leadership.

- Keep raising the bar for how Pleo supports its most complex customers, from the first conversation to real value realised.

WHAT YOU BRING

You’ll thrive in this role if you have:

- 8+ years of experience in customer onboarding, enterprise implementation, customer success, customer enablement or a related customer-facing function

- 4+ years leading people, ideally in enterprise onboarding, implementation, solutions, or customer success teams

- A track record of delivering onboarding or implementation programmes at enterprise tech companies

- Experience with large, complex customers, multiple stakeholders, regions, entities, workflows or technical dependencies

- A relationship-first leadership style, and the ability to earn trust with senior customer stakeholders quickly.

- Real executive presence: you're comfortable presenting to CFOs, finance leaders, technology leaders, and executive sponsors.

- Experience leading technical conversations with Product team covering integrations, security, data or configuration

- Experience building enablement programmes for…