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 GTM Enablement Manager (Mid-Market and Enterprise) to join our GTM Enablement team at Pleo. In this role, you'll design and deliver world-class enablement programs for our mid-market and enterprise sales functions, and be part of a team driving Pleo's ambitious move upmarket. If you're excited about shaping how complex, high-value deals get won at scale and are passionate about developing elite sales talent, then 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 teams in sales, Revenue Operations, Product Marketing and Product. Our GTM Enablement team is highly collaborative and dedicated to unlock commercial performance across Pleo's go-to-market organisation. You'll also have the chance to partner with Sales Leadership and cross-functional stakeholders to drive alignment and capability uplift as we scale upmarket

What you’ll be doing

As a GTM Enablement Manager, you will:

Own upmarket enablement end to end: Design, implement, and manage enablement programs tailored specifically to mid-market and enterprise sales motions, from onboarding new hires through to ever boarding for tenured sellers
Build enterprise sales capability: equip Account Executives, Account Managers, and support roles with mastery of complex sales skills: multi-threaded stakeholder engagement, executive discovery, value selling, business case development, MEDDPICC, competitive displacement, and mutual close planning
Drive coaching and development: lead deal coaching, win/loss reviews, and role-based competency frameworks that continuously raise the bar for our upmarket sales teams
Collaborate cross-functionally: partner with Sales Leadership, RevOps, Product Marketing, and Product to ensure enablement is aligned to commercial strategy and directly tied to business outcomes
Deliver impactful content: create and manage high-quality enablement content across on-demand and in-person formats, including live workshops with experienced sellers, leveraging tools like Sana, Tella and Canva
Beyond sales, you will also support enablement across our Customer Success and Customer Support functions - helping these teams deliver a consistently excellent experience to our mid-market and enterprise customers through onboarding, product knowledge, and customer-facing skills programs.

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:

Deep B2B SaaS enablement experience: At least 3 years in Sales Enablement (or a closely related L&D function) with a clear track record of enabling mid-market and enterprise sales teams; or +5 years of SaaS sales experience in complex, multi-stakeholder deals with a strong passion for coaching others
Enterprise methodology expertise: practical, hands-on knowledge of frameworks like MEDDPICC, Command of the Message, Challenger, or Force Management, and proven ability to operationalise them across a sales team
Strong communication and facilitation skills: Comfortable presenting to senior commercial audiences and designing content that lands with experienced sellers
A data informed mindset: Experience with survey design, analysis, and connecting enablement initiatives directly to commercial outcomes
A hands-on, strategic approach: The ability to execute day-to-day while thinking about the bigger picture; you build credibility with senior sellers and leaders through expertise, not just authority
Experience with LMS/CMS platforms (eg. Sana) and content creation tools (eg Tella, Canva, Google Slides)
Familiarity with sales stack tools (Hubspot, Salesforce, Gong, Cognism) and experience integrating AI into L&D programs is a strong plus.
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 enabled enterprise or mid-market sales teams before and want to own the function end-to-end in a fast-scaling, product-led company.
You thrive in roles where you need to be both a strategic partner to senior leaders and a hands-on builder of programs and content.
You're energised by the challenge of helping experienced sellers get even better, and you have the credibility and communication skills to make that happen.

This role is not a good fit for you if:

Your experience is primarily in SMB or transactional sales enablement and you haven't worked with complex, multi-stakeholder enterprise cycles.
You prefer a stable, defined scope, this role is continuously evolving as Pleo moves upmarket, and ambiguity is part of the job.
You're looking for a role where you mainly manage content or tools, rather than directly influencing seller capability and commercial outcomes.

How you’ll develop in this role

In your first 6 to 12 months at Pleo, you’ll:

Build a deep understanding of Pleo's upmarket sales motion, ICP, and competitive landscape, and use it to shape your enablement strategy.
Launch or significantly evolve segment-specific onboarding and everboarding programs for mid-market and enterprise roles.
Grow your influence across the commercial organisation, establishing yourself as a trusted partner to Sales Leadership and contributing to revenue outcomes.

The location

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

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
We offer 25 days of holiday + your public holidays
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:

Intro call: A 30-minute chat with our Talent Acquisition Partner to discuss the role and your background.
Hiring Manager Interview: A 45 mins interview with the Hiring Manager to go deeper on your experience and how your profile can adapt to the role
Pleo Challenge: We will send you a take home test and invite you to present it during a 60 minute team interview. This is an opportunity to show us how you would handle the day to day of the role
Final Interview: A final interview with a Senior Leader

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 a similar role, we received a vast amount of 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.
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.