GTM Enablement Specialist

Pleo · Madrid, Madrid · London, England · Lisbon, Lisbon

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 an Enablement Specialist to join our GTM Enablement team at Pleo. In this role, you'll own the delivery and measurable impact of enablement programmes across Go-to-Market functions. You'll report to the Revenue Operations Director and work closely with our GTM Enablement Manager. If you're excited about making enablement sticks, driving adoption at scale, and working in a fast-moving, data-driven function, this is the opportunity for you.

WHO YOU’LL BE WORKING WITH AND REPORTING TO

You'll report to our Director, GTM Enablement and work closely with our GTM Enablement Manager as well as teams in sales, Revenue Operations, Product Marketing and Product. Our GTM Enablement team is highly collaborative and dedicated to unlocking commercial performance across Pleo's go-to-market organisation.

WHAT YOU’LL BE DOING

As a GTM Enablement Specialist you will:

• Own enablement programme delivery end to end Work with external suppliers and internal subject experts to design, implement, and manage enablement programmes tailored to GTM functions, from kickoff through launch and adoption. Manage timelines, dependencies, stakeholder alignment, and iterative feedback loops to ensure successful execution and behaviour change aligned to performance indicators.

• Run the enablement intake and calendar. Manage a single intake process for enablement requests, so every request comes with a clear why, an owner and a realistic lead time. Maintain a monthly enablement calendar visible to the whole GTM organisation.

• Drive adoption and behaviour change Move beyond content delivery to ensure programmes actually change how people work. Co-facilitate live sessions, develop supporting materials and e-learning, gather real-time feedback, and iterate quickly. Understand what reinforcement looks like and how to embed learning into ongoing work.

• Measure impact and report on ROI Build dashboards that track completion, engagement, and business outcomes. Connect enablement activity to commercial metrics (win rates, deal velocity, customer outcomes). Report transparently on what's working, what's not, and what we should double down on.

• Partner on content and validate quality Work with subject-matter experts to validate enablement content for accuracy, relevance, and fit-for-purpose. Gather field feedback from reps and managers, iterate rapidly, and ensure content lands with real sellers in real deals.

• Collaborate cross-functionally and own stakeholder relationships Be a trusted point of contact for Go-to-Market managers and leaders (Sales, Customer Success, Partnerships). Keep them updated on programme progress, blockers, and outcomes. Build credibility through expertise and clear communication of impact.Partner with Sales Leadership, RevOps, Product Marketing, and Product to ensure enablement is aligned to commercial strategy and directly tied to business outcomes

• Diagnose and solve delivery challenges When a programme isn't landing or blockers emerge, help to diagnose the root cause, drive timely solutions, and escalate strategically to maintain momentum.

• Run onboarding. Coordinate GTM onboarding end to end and help reduce ramp time and time to first deal.

• Leverage technology and tools Use Sana Learn for platform management and content hosting. Work with Gong to analyse real calls and identify enablement gaps. Familiarise yourself with Hubspot for data. Explore how AI tools can accelerate content creation and personalised learning. To put things into context, we're currently scaling our mid-market and enterprise segment in various regions, and investing heavily in the skills, content, and infrastructure needed to support longer, more complex sales cycles. You can expect to work with tools including Hubspot, Gong, Sana, and AI-powered learning technologies.

WHAT YOU BRING

You’ll thrive in this role if you have:

• Enablement or GTM-adjacent experience 3–5 years in Sales Enablement, L&D, or Go-to-Market operations. Track record of owning programmes end-to-end and knowing what it takes to make learning stick. Or 5+ years of SaaS sales experience with a strong passion for coaching and developing others.

• Programme delivery capability Proven ability to manage complex programmes from design through adoption. You understand the difference between one-off training and systemic behaviour change. You think in phases: awareness → skill-building → reinforcement → measurement.

• Data and measurement mindset Comfortable with data analysis and dashboard reporting to analyse performance. Experience connecting enablement initiatives to commercial outcomes (deal velocity, win rates, customer retention). You care about ROI, not just completion metrics.

• Stakeholder management and communication Ability to build trust with commercial leaders and function heads. You communicate clearly, translate between technical and business language, and escalate smartly. You're credible with experienced sellers, not just through title but through expertise.

• Facilitation and coaching Comfortable delivering live programmes, providing feedback, and coaching managers through adoption challenges. You can present confidently to senior commercial audiences and engage experienced sellers.

• LMS and content creation tools Familiarity with Sana or similar LMS platforms. Comfort using content creation tools (Canva, Tella, Google Slides) to build professional learning assets.

• Sales stack familiarity Working knowledge of Hubspot, Gong, Cognism, LinkedIn Sales Navigator. Understanding of how these tools connect and where data lives. Experience integrating AI into Enablement programmes is a strong plus.

• Hands-on and strategic The ability to execute day-to-day programme work while thinking about the bigger picture. You build programmes, not just manage them. You're not afraid to roll up your sleeves and solve the granular problems that get in the way of adoption.

• Fluency in English; an additional European language (German or Spanish) is a strong plus.

WHY IS THIS ROLE A GOOD FIT FOR YOU

This role is a good fit for you if:

• You've delivered enablement programmes in B2B SaaS environments and want to own the end-to-end function in a fast-scaling company moving upmarket.

• You thrive in roles where you're both a trusted partner to commercial leaders and a hands-on builder of programmes and content.

• You're energised by the challenge of making enablement work—connecting the dots between content, adoption, behaviour change, and business outcomes.

• You're comfortable with ambiguity and excited about helping to shape an enablement function as it scales and specialises. This role is continuously evolving as Pleo scales, and ambiguity is part of the job.

• You want to work in a data-driven environment where impact is measured and communicated clearly.

THE LOCATION

Please note: We can hire on a hybrid or in-person setup 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.

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 with great success so far

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

THE INTERVIEW PROCESS

We want to ensure you are set-up for success and understand what will be expected of you. If your application is successful, our interview process is as follows:

1. Intro call: A 30-minute chat with our Talent Acquisition Partner to discuss the role and your background.

2. Hiring Manager Interview: A 45-minute interview with the hiring manager to go deeper on your experience and how your profile fits the role.

3. Pleo Challenge: A take-home test followed by a 60-minute team interview. This is your opportunity to show us how you'd handle the day-to-day of the role (e.g., designing a programme, measuring impact, stakeholder communication).

4. Final Interview: A final interview with a Senior Leader (Adrienne, CRO).

Transparency is important to us so we also wanted to share some insights about what we’re looking for in applications to ensure you can set yourself up for success!

Last time we hired for this role, we received a vast number applications but only a few were selected for an intro call. Some of the key reasons why previous candidates didn’t make it past the application screening stage include:

• CV writing and content: we receive a lot of CVs, and many of them are AI-generated. We love seeing people leverage AI—it’s a big focus for us internally too—but without human intervention, these CVs can sometimes become generic and fail to show a candidate in the best light. What we're really looking for is the specific details of real impact that only you know from your previous experience. A top tip from us is to use the “Achieved X, as measured by Y, by doing Z” formula (credit: Laszlo Bock, ~2014) to give a really clear picture of what you’ve worked on. A final note: including links to your previous companies' websites is a huge help and allows us to truly understand your background!

• Application care: every single application we receive is reviewed by a human (yes, hundreds of them) because we believe that candidates' efforts should be matched by an equal level of human care. This means that we expect a similar level of attention put into your application. Read and answer the application questions carefully, they make a huge difference in our decision-making process.

• Profile to role fit: highlight most important aspects of the role, points that might get misunderstood, any specific industry requirements etc.

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 https://www.pleo.io/en/legal.

• 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.

Apply on Pleo's site