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 Program Manager, Digital Content & Self-Serve CX to join our Customer Experience team at Pleo. In this role, you’ll help design, scale, and improve the digital customer experience across help content, help center strategy, community, education content, self-service journeys, and CX programs that reduce friction and improve customer outcomes.

This role is ideal for someone who understands that great customer experience is not only delivered by people, but also through clear content, intuitive self-help, smart automation, and scalable digital experiences. You will act as an individual contributor with no direct reports, but you will be expected to lead through influence, cross-functional coordination, and strong program ownership.

You should bring prior Customer Experience experience and a strong point of view on how digital content, self-service, AI, and automation can work together to improve customer outcomes, reduce effort, and support scale.

Who you’ll be working with and reporting to

You’ll report to the Manager of Customer Success and work closely with teams across Support, Customer Success, Onboarding, Product, Product Operations, Engineering, Marketing, Data, and RevOps.

Our team is highly collaborative and focused on improving the end-to-end customer experience through better journeys, stronger content, scalable self-service, and smarter operating models. You’ll partner with stakeholders across the business to ensure customers can find answers faster, solve more on their own, and have a more seamless digital experience.

What you’ll be doing

As a Program Manager, Digital Content & Self-Serve CX, you will:

• Own and drive programs across digital content and self-service CX including help center strategy, knowledge content, education content, customer community, and self-help journeys.

• Lead improvements to the help center experience by identifying content gaps, structural issues, search friction, and opportunities to improve findability, usefulness, and resolution.

• Drive digital content strategy across customer education, support content, onboarding guidance, FAQs, and scalable knowledge experiences that help customers achieve outcomes faster.

• Build and improve self-serve customer journeys that reduce customer effort, improve issue resolution, and support stronger time-to-value.

• Partner with cross-functional teams to launch AI and automated self-serve solutions including intelligent guidance, workflow automation, chatbot experiences, content recommendations, and other digital support mechanisms.

• Use customer insight and operational data to prioritise improvements by analysing content usage, deflection opportunities, search behaviour, case drivers, friction points, and customer feedback.

• Coordinate CX programs tied to digital experience improvement across content, education, support, onboarding, and community.

• Establish measurement and reporting for digital self-service performance including adoption, engagement, content usefulness, containment, search success, case avoidance, and customer effort.

• Drive governance and content quality standards to ensure self-service experiences stay accurate, current, useful, and aligned to product and customer needs.

• Partner with Product, Support, and CX leaders to ensure digital self-service is treated as a strategic lever for customer experience, scale, and operational efficiency.

To put things into context

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

• improving help center structure, content quality, and search experience

• building a stronger digital education and self-help strategy

• expanding scalable onboarding and product education content

• strengthening customer community engagement and value

• identifying self-service gaps that create avoidable support demand

• introducing AI and automation into self-serve experiences

• improving how digital content supports customer success and support outcomes

• connecting content and self-service performance to broader CX priorities

You can expect to work across a tech environment that includes help center and knowledge tools, CRM, support tooling, community platforms, customer education tools, AI and automation solutions, BI/reporting tools, workflow tools, and collaboration platforms.

Examples: Zendesk or similar, Salesforce, Gainsight or similar, learning/content platforms, chatbot and AI tools, Looker/Tableau/Power BI, Jira/Asana, and Slack.

What you bring

You’ll thrive in this role if you have:

• Program management experience in Customer Experience, Digital CX, Content Operations, Support Operations, Customer Education, Knowledge Management, or a similar function.

• Prior Customer Experience experience with a strong understanding of how digital touchpoints impact customer effort, satisfaction, resolution, and outcomes.

• Experience leading or supporting help center, self-service, knowledge, education content, or community programs in a SaaS, fintech, or digital environment.

• Experience driving AI and automated solutions for self-service including chatbot optimisation, intelligent content experiences, automated workflows, or related digital support capabilities.

• A structured, analytical mindset with the ability to identify friction, prioritise improvements, and translate insight into action.

• Strong cross-functional collaboration skills and the ability to work effectively with Product, Engineering, Support, Success, Marketing, and Data teams.

• Strong written communication and content judgment with the ability to improve clarity, usefulness, and consistency across customer-facing content.

• Experience with reporting and performance metrics related to digital content, self-service, search, case drivers, content engagement, or customer effort.

• Strong execution skills with the ability to manage multiple workstreams and move initiatives forward without direct authority.

• A builder mentality with energy for improving systems, content, journeys, and self-service experiences in a scaling environment.

Nice to have

• Experience with knowledge management, help center platforms, or content operations

• Experience with customer education programs, academies, or learning content

• Familiarity with community strategy and customer engagement programs

• Exposure to journey mapping, service design, automation strategy, or conversational AI

• Experience in fintech, spend management, B2B SaaS, or digital product environments

Why is this role a good fit for you

This role is a good fit for you if:

• You believe great content and self-service are core parts of great customer experience.

• You enjoy building scalable digital solutions that help customers solve problems faster and more independently.

• You are strong at connecting customer needs, content strategy, and operational execution.

• You like working across teams to improve journeys, reduce friction, and create smarter ways for customers to get help.

• You want to help shape how AI and automation improve self-serve customer experiences in a practical, measurable way.

This role is not a good fit for you if:

• You are looking for a people-management role with direct reports.

• You prefer brand or marketing content over operational, educational, and support-oriented content.

• You do not enjoy working across multiple stakeholders to improve systems, processes, and customer journeys.

• You are uncomfortable owning metrics, prioritising trade-offs, or driving change through influence.

• You are not interested in AI, automation, or scalable self-service as part of the customer experience strategy.

How you’ll develop in this role

In your first month at Pleo, you’ll:

• Learn the current help center, self-service, education, and community landscape.

• Build a view of where customers experience friction across digital content and self-help journeys.

• Assess current performance, gaps, and opportunities across help content, findability, search, and automation.

• Start improving visibility and prioritisation for high-impact digital CX opportunities.

In your first 6 months, you’ll:

• Deliver improvements to help center structure, self-service journeys, and content governance.

• Begin driving measurable progress in content effectiveness, self-service adoption, and customer effort reduction.

• Launch or improve targeted AI and automation use cases that support self-serve resolution and scale.

• Become a trusted program owner for digital CX and self-service improvement initiatives.

In your first 12 months, you’ll:

• Help establish a stronger self-service operating model across content, education, help, and community.

• Deliver measurable gains in content performance, self-serve success, and digital customer experience.

• Improve the connection between customer insight, case drivers, and digital content prioritisation.

• Be recognised as a strong program owner who helps Pleo scale a smarter, more effective self-serve experience.

Success in this role looks like

• Help center and self-service experiences are easier to use, easier to trust, and more effective.

• Customers can find answers faster and solve more on their own.

• Education content is more aligned to customer needs and lifecycle moments.

• AI and automated self-serve solutions are implemented in practical ways that improve experience and reduce friction.

• Content gaps, search issues, and recurring case drivers are more visible and better prioritised.

• Digital content and self-service become stronger contributors to CX quality, scale, and operational efficiency.

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.