GTM Enablement 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 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. S