Digital Onboarding Specialist I - Lisbon / Madrid

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 Digital Onboarding Solutions Specialist to join our Digital Onboarding Solutions team at Pleo. In this role, you'll help customers who have got stuck while onboarding themselves onto Pleo, unblock them, and make sure they get to a successful first spend. You'll also help us find and fix the friction that causes these blockers in the first place. If you enjoy solving real problems for real people, and you care about making onboarding work better for everyone, then this is the opportunity for you!

Who you'll be working with and reporting to

You'll report to our Manager, Onboarding and work closely with the Digital Onboarding Solutions Manager. Our team is highly collaborative and dedicated to getting every new customer to a smooth, successful start on Pleo. You'll also have the chance to partner with teams across Product, Growth, Sales, Support and RevOps to remove friction for our customers.

What you'll be doing

As a Digital Onboarding Solutions Specialist, you will:

• Monitor escalation channels, handle live chats during coverage hours, diagnose blockers, and agree next steps with customers.

• Pick up Freshdesk tickets raised outside live chat hours, reply by email the next business morning, and offer a call when needed.

• Schedule and run calls with customers who are blocked during self-onboarding and have escalated via chat or email.

• Coordinate internally on specialist escalation consultations and take ownership of seeing each case through to resolution.

• Record the stage, blocker and outcome for every account, and run 1–2 week progress checks to keep customers moving.

• Work closely with the Digital Onboarding Solutions Manager to improve our processes by flagging inefficiencies and proposing fixes.

• Run proactive outreach on stalled accounts before they churn or give up.

What you bring

You'll thrive in this role if you have:

• Experience in customer support, customer success, onboarding or another role where you help people get unstuck quickly.

• A clear, structured approach to diagnosing problems: you ask the right questions, find the real blocker, and agree a next step.

• Confidence running calls with customers, including those who are frustrated or short on time. • Strong attention to detail and the discipline to record stage, blocker and outcome consistently.

• A continuous improvement mindset, and the willingness to raise inefficiencies and help fix them with others.

• Comfort working across different channels (live chat, email, calls) and managing your own queue.

• Working hours are 9am–5pm.

Why is this role a good fit for you

This role is a good fit for you if:

• You get satisfaction from turning a stuck customer into a happy one.

• You like spotting patterns, asking why something keeps going wrong, and doing something about it.

• You are organised and enjoy owning a caseload from start to finish.

• This role is not a good fit for you if:

• You prefer to work without regular contact with customers.

• You find it hard to switch between many open cases and channels in a single day.

How you'll develop in this role

In your first several weeks at Pleo, you'll:

• Build deep knowledge of Pleo's product and the most common onboarding blockers, so you can resolve cases faster.

• Take ownership of your own caseload and proactive outreach to stalled accounts.

• Work with the Digital Onboarding Solutions Manager and cross-functional partners to improve a process or flow that is blocking customers. We're committed to helping you develop your career, whether that means taking on more complex escalations, stepping into a Team Lead role, or building new skills in onboarding design, product, marketing, and digital funnel building.

Show me the benefits

• Your own Pleo card (no more out-of-pocket spending!)

• Lunch is on us for your work days: enjoy catered meals or receive a lunch allowance based on your local office.

• Comprehensive private healthcare: depending on your location, coverage options include Vitality, Alan or Médis.

• 25 days of annual leave + public holidays (additional days may apply in select countries based on local standards).

• For our team, we offer both hybrid and fully remote working options.

• We use MyndUp to give our employees access to free mental health and well-being support.

• Paid parental leave: we want to make sure we're supportive of families and help you feel you don't have to compromise your family due to work.

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.