Senior Enterprise Customer Success Manager

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 Enterprise Customer Success Manager to join our Customer Experience team at Pleo. In this role, you’ll own a portfolio of large, complex, and strategically important enterprise customers, helping them achieve measurable business outcomes, expand adoption, manage change, and build long-term value with Pleo.

You’ll serve as a trusted advisor to senior customer stakeholders while coordinating the broader Pleo relationship across Customer Success, Product, Support, Sales, Finance, and other internal teams.

This is not a reactive account-management role. You’ll be expected to understand each customer’s business priorities, operating model, success criteria, and risk profile. You’ll turn that understanding into clear success plans, executive engagement strategies, adoption programs, renewal plans, and growth opportunities.

The right candidate will bring at least three years of direct experience managing enterprise customers, along with the communication skills, commercial judgment, and operational discipline required to manage high-value relationships in a fast-paced technology environment.

Who you’ll be working with and reporting to

You’ll report to our Manager of Customer Success, Large & High-Growth Customers and work closely with teams across:

• Customer Support

• Customer Onboarding

• Sales and Account Management

• Product and Product Operations

• Revenue Operations

• Finance

• Data and Analytics

• Program Management and Operations

You’ll work with customer stakeholders across finance, procurement, operations, technology, transformation, and executive leadership.

You’ll be responsible for creating alignment across these stakeholders, establishing clear governance, and ensuring Pleo remains connected to the customer’s evolving strategic and operational priorities.

What you’ll be doing

As a Senior Enterprise Customer Success Manager, you will:

• Own a portfolio of enterprise customers with accountability for customer health, value realisation, adoption, retention, renewal readiness, advocacy, and growth.

• Build trusted relationships with senior and executive stakeholders, positioning yourself as a credible advisor who understands their business priorities and operating environment.

• Develop detailed customer success plans that connect the customer’s strategic goals to measurable outcomes, adoption milestones, responsibilities, and timelines.

• Lead executive business reviews and strategic customer meetings that demonstrate value, address risks, align stakeholders, and create clear next steps.

• Drive product adoption across complex customer organisations, helping customers expand usage across teams, entities, locations, use cases, and workflows.

• Create and maintain detailed stakeholder maps, identifying decision-makers, champions, influencers, operational contacts, blockers, and executive sponsors.

• Identify churn risk early using product usage, engagement, stakeholder, support, financial, organisational, and external business signals.

• Build and execute churn-prevention plans with clear actions, owners, timelines, customer commitments, and executive escalation paths.

• Maintain detailed and accurate forecasts across renewals, risk, customer health, expected outcomes, growth opportunities, and major account milestones.

• Lead renewal-readiness activities by ensuring customer value is documented, risks are addressed, stakeholders are aligned, and commercial partners have accurate account intelligence.

• Identify and support expansion opportunities by connecting additional Pleo capabilities, products, or use cases to the customer’s evolving business needs.

• Coordinate complex customer escalations across Support, Product, Engineering, Finance, and other teams while maintaining clear and confident customer communication.

• Act as the customer’s internal advocate, ensuring customer needs, feedback, risks, and opportunities are visible to the right stakeholders at Pleo.

• Navigate customer change effectively, including leadership transitions, reorganisations, acquisitions, market expansion, platform changes, and evolving business priorities.

• Track customer commitments and outcomes with strong operational discipline, ensuring actions are documented, owned, and completed.

• Contribute to the evolution of Pleo’s enterprise Customer Success model by sharing best practices, customer insights, playbooks, and recommendations.

• Support peer development and knowledge sharing across the Customer Success team without holding direct people-management responsibility.

To put things into context

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

• strengthening relationships with Pleo’s largest and most strategic customers

• improving enterprise customer retention and renewal predictability

• increasing adoption across complex customer organisations

• creating stronger executive engagement and governance

• identifying churn risk before it becomes a renewal issue

• improving forecast accuracy and account visibility

• coordinating complex customer needs across multiple internal teams

• helping customers quantify and communicate the value they receive from Pleo

• identifying opportunities for expansion and deeper product adoption

• improving the consistency and quality of enterprise success planning

• helping customers navigate operational and organisational change

• turning customer feedback into actionable Product and CX insight

You can expect to work across a technology environment that includes CRM, Customer Success platforms, support systems, product analytics, business intelligence tools, workflow tools, and collaboration platforms.

Examples may include Vitally, Gainsight or similar, Zendesk, Looker, Tableau or Power BI, Jira, Asana, and Slack.

What you bring

You’ll thrive in this role if you have:

• At least three years of direct enterprise Customer Success or strategic account-management experience, managing large, complex, and high-value B2B customers.

• Five or more years of overall experience in Customer Success, account management, consulting, implementation, or a related customer-facing role.

• Experience working in SaaS, fintech, enterprise technology, or another complex B2B technology environment.

• A proven record of retaining and growing enterprise customers, including managing renewals, adoption, risk, and value realisation.

• Strong executive relationship-management skills, with the confidence and credibility to engage senior decision-makers and business leaders.

• Experience managing complex stakeholder environments involving multiple teams, business units, regions, entities, or decision-makers.

• Strong churn-prediction and prevention skills, including the ability to interpret customer signals, identify root causes, and build effective recovery plans.

• Detailed forecasting experience across renewals, customer risk, account health, adoption, and expansion opportunities.

• Strong commercial judgment, with an understanding of how customer outcomes connect to retention, revenue, expansion, and long-term account value.

• Excellent verbal and written communication skills, including the ability to lead difficult conversations, present to executives, and simplify complex issues.

• Experience building strategic success plans, account plans, stakeholder maps, and executive business reviews.

• Strong analytical skills, with the ability to interpret customer data, product usage, service trends, and business information.

• Strong cross-functional leadership skills, with the ability to align internal stakeholders without relying on direct authority.

• A structured and proactive approach to account management, with excellent follow-through and attention to detail.

• Comfort working in a fast-paced growth environment where customer expectations, internal priorities, and business needs can evolve quickly.

• The ability to balance strategic relationship management with detailed operational execution.

Nice to have

• Experience in fintech, payments, spend management, financial operations, or expense-management technology

• Experience working with finance leaders, procurement teams, controllers, CFO organisations, or transformation leaders

• Experience managing multi-country or multinational enterprise customers

• Familiarity with ERP, accounting, procurement, or financial-system integrations

• Experience supporting customers through significant organisational or technology transformation

• Exposure to AI-enabled Customer Success, predictive health models, automated risk detection, or digital engagement

• Experience partnering with Product teams on strategic customer feedback and roadmap discussions

• Experience managing accounts with complex security, compliance, governance, or implementation requirements

Why is this role a good fit for you?

This role is a good fit for you if:

• You enjoy building strategic relationships with complex enterprise customers.

• You are comfortable engaging senior leaders and navigating high-stakes customer situations.

• You know how to connect product adoption to measurable customer outcomes.

• You are proactive about identifying and addressing churn risk.

• You combine strong relationship skills with rigorous account-management discipline.

• You are confident leading executive reviews, renewal discussions, and difficult customer conversations.

• You enjoy coordinating internal teams around complex customer needs.

• You want direct responsibility for protecting and growing some of Pleo’s most important customer relationships.

This role is not a good fit for you if:

• You have not directly managed enterprise or strategic customer relationships.

• You prefer transactional or high-volume customer portfolios.

• You are uncomfortable owning customer risk, retention, and renewal readiness.

• You prefer reacting to customer requests rather than building proactive engagement strategies.

• You are uncomfortable engaging executive stakeholders or leading difficult conversations.

• You do not enjoy detailed forecasting, CRM management, and account planning.

• You prefer working independently without significant cross-functional coordination.

• You are looking for a people-management role rather than a senior individual-contributor position.

How you’ll develop in this role

In your first 1 month at Pleo, you’ll:

• Learn Pleo’s product, enterprise customer journey, value proposition, and Customer Success operating model.

• Build a detailed understanding of your customer portfolio, including revenue, renewal dates, usage, stakeholders, open issues, risks, and growth potential.

• Establish relationships with key customer stakeholders and internal account partners.

• Review and improve success plans, stakeholder maps, account plans, and risk assessments.

• Establish clear operating rhythms for customer engagement, internal coordination, and forecasting.

• Identify immediate risks, adoption gaps, and opportunities across your portfolio.

In your first 3 months, you’ll:

• Lead consistent executive and operational engagement across your customer portfolio.

• Improve customer success planning, value documentation, and renewal readiness.

• Strengthen the accuracy and detail of customer health and renewal forecasts.

• Deliver measurable progress against adoption, engagement, and customer outcome goals.

• Build and execute mitigation plans for at-risk customers.

• Identify and support qualified expansion opportunities.

• Become a trusted advisor to customer stakeholders and a reliable source of account intelligence internally.

In your first 5 months, you’ll:

• Build a healthy and well-managed portfolio of enterprise customers.

• Deliver strong retention and renewal performance.

• Improve adoption and value realisation across complex customer organisations.

• Develop trusted relationships with senior and executive customer stakeholders.

• Demonstrate strong forecast accuracy and proactive risk management.

• Contribute repeatable best practices and insight to Pleo’s broader enterprise Customer Success model.

• Be recognised as a senior individual contributor capable of managing Pleo’s most important and complex customer relationships.

Success in this role looks like

• Enterprise customers have clear success plans connected to measurable business outcomes.

• Executive and operational customer relationships are strong and multi-threaded.

• Customer risks are identified early and addressed through structured mitigation plans.

• Renewal forecasts are detailed, accurate, and supported by clear account evidence.

• Customers demonstrate stronger product adoption and value realisation.

• Escalations are managed with urgency, clarity, and strong customer communication.

• Internal teams are aligned around customer priorities, responsibilities, and next steps.

• Renewal and retention performance is strong across the assigned portfolio.

• Expansion opportunities are identified through customer value and business need rather than transactional selling.

• Pleo is viewed as a strategic partner rather than simply a product provider.

Candidate profile summary

The strongest candidate for this role is an experienced enterprise Customer Success professional who combines senior-level relationship skills with commercial awareness, analytical thinking, and disciplined account execution.

They have at least three years of direct enterprise experience and are comfortable managing complex customers with multiple stakeholders, high expectations, and significant revenue impact.

They know how to earn executive trust, demonstrate value, predict and prevent churn, maintain accurate forecasts, and mobilise cross-functional teams around customer outcomes. They are proactive, credible, highly organised, and capable of protecting and growing Pleo’s most strategic customer relationships.

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.

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• 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.