Senior Manager, Onboarding (high-touch customers)

Pleo

United States

Hybrid

USD 180,000 - 240,000

Full time

14 days+

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Benefits offered by this job

Pleo card

Lunch allowance

Job summary

Pleo is seeking a Senior Manager, Onboarding to lead the strategy, operating model, and team responsible for onboarding its largest, most complex customers. You’ll drive end-to-end programs, from discovery and implementation planning through configuration, integrations, enablement, go-live, and handover to Customer Success.

You’ll partner with Finance, Product, Engineering, Sales, and senior executives to ensure value delivery, measurable outcomes, and strong governance, while developing a

Qualifications

8+ years of experience in customer onboarding and enterprise implementation.
4+ years leading people, ideally in enterprise onboarding or customer success teams.
Proven track record delivering onboarding programs at enterprise tech companies.
Experience with large, complex customers, multiple stakeholders, regions, entities, or dependencies.
Relationship-first leadership style with quick trust-building with senior stakeholders.
Executive presence: comfortable presenting to CFOs, technology leaders, and sponsors.
Experience leading technical conversations with product/engineering on integrations and security.
Experience building enablement programs for diverse audiences.
Strong people-management and coaching skills for high-performing teams.
Commercial awareness: onboarding quality affects adoption, retention, revenue, and growth.
Strong cross-functional leadership to influence without direct authority.
Data-driven, disciplined approach using metrics and forecasts.

Responsibilities

Lead the onboarding strategy for the largest and most complex customers.
Manage and grow Enterprise Onboarding and Enablement Managers.
Oversee end-to-end onboarding from discovery to handover to Customer Success.
Build relationships with senior stakeholders and connect business value to customer goals.
Govern programmes with scope, milestones, owners, decisions, and risks.
Ensure alignment with Sales, Product, Engineering, and Security during handover.
Develop governance and a steady rhythm of steering calls for key programmes.
Drive adoption and enablement programs to ensure effective use of our solutions.
Be the voice of the enterprise customer inside Pleo to reduce blockers and friction.

Skills

Enterprise onboarding

Team leadership

Executive presence

Cross-functional collaboration

Data-driven decision making

Stakeholder management

Customer success

Program management

Job description

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 different audiences

Strong people-management and coaching skills, with a record of building high-performing, customer-facing teams.

Commercial awareness: you understand how onboarding quality affects adoption, retention, customer confidence, revenue, and account growth over time.

Strong cross-functional leadership, you can influence teams and leaders even without direct authority over them.

A data-driven, disciplined approach: you use metrics, forecasts, and customer signals to guide decisions.

Comfort with fast-paced growth

Why is this role a good fit for you

This role is a good fit for you if:

You think in outcomes, not tickets. You want onboarding to prove value to the customer, not just tick off a technical implementation

You like leading a team through complexity, juggling multiple stakeholders, competing priorities, and the occasional at‑risk programme doesn't rattle you, it's where you do your best work.

You'd rather be in the room with a CFO than behind a project plan, you enjoy building trust with senior stakeholders and leading high‑stakes conversations, not just coordinating tasks.

This role is not a good fit for you if:

You prefer a narrower, more predictable scope, this role spans strategy, people leadership, executive relationships, and hands‑on risk management, all at once.

You'd rather stick to the technical side of implementation, this role needs you to hold the business case as tightly as the technical detail, and move fluidly between the two.

You're looking for a purely individual‑contributor role, leading and developing a team is core to this job, not a side responsibility.

How you’ll develop in this role

In your first 6 months at Pleo, you’ll:

Build a mature and repeatable enterprise onboarding and enablement operating model.

Deliver measurable improvements in time-to-value, go-live success, adoption, and customer satisfaction.

Establish stronger relationships and governance across Pleo’s largest customer implementations.

Reduce implementation delays caused by unclear ownership, technical dependencies, or stakeholder misalignment.

Improve how customer value is defined, positioned, measured, and transferred into ongoing Customer Success plans.

Be recognised as a key leader in how Pleo launches, enables, and retains large enterprise customers.

The location

Please note: We can hire on a hybrid set-up in any of the locations listed on the advert but you will need to be physically based in the country of your choice with a valid right to work. We are unable to offer visa sponsorship for this role in any of the listed locations.

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