Head of Enterprise Sales, Leo FM

<p><strong>Leo FM</strong></p> <p>Leo FM is a leading full-suite facilities maintenance company combining in-house self-perform capabilities with a national network of specialist service partners. We deliver responsive, high-quality services across a wide range of verticals (logistics, healthcare, retail, manufacturing, education, banking, etc.).</p> <p>We’re scaling rapidly and looking for a seasoned enterprise sales leader to drive large, complex deals with major commercial, institutional, and national accounts.</p> <p><strong>Role Overview</strong></p> <p>As <strong>Head of Enterprise Sales,</strong> you will own revenue generation from large-scale, strategic IFM customers. You will design and execute a scalable, repeatable sales motion for complex facility services contracts. You’ll coordinate closely with operations, marketing, and service delivery to ensure seamless execution and customer satisfaction.</p> <p>This is a high-impact, high-visibility role: you will set the strategic direction for enterprise sales and be a key driver of the company’s growth trajectory.</p> <p><strong>Key Responsibilities</strong></p> <ul> <li>Build, refine, and execute a go-to-market strategy for enterprise accounts (national chains, multi-site portfolios, institutional clients).</li> </ul> <ul> <li>Forecast pipeline and revenue, set targets, monitor sales metrics (win rates, sales cycles, average deal size, churn, etc.).</li> </ul> <ul> <li>Own and manage large, multi-site, multi-year RFPs and contract negotiations with senior stakeholders (C-suite, facility directors).</li> </ul> <ul> <li>Collaborate with marketing, operations, service delivery, and finance to build compelling proposals, pricing models, value propositions, and support the full sales lifecycle.</li> </ul> <ul> <li>Drive customer relationship management at the executive level, upsell / cross-sell opportunities, renewals, and account expansion.</li> </ul> <ul> <li>Analyze market trends, competition, pricing, and product mix to refine positioning and differentiate Leo FM’s offering.</li> </ul> <ul> <li>Develop scalable processes, tools, sales enablement resources, and operational rigor to support growth.</li> </ul> <ul> <li>Report regularly to executive leadership on sales performance, forecasts, risks/opportunities, and strategic insights.</li> </ul> <p><strong>Required Experience &amp; Skills</strong></p> <ul> <li>15+ years of enterprise B2B sales experience, ideally in facility services, facilities management, building services, real estate services, or a related services industry.</li> </ul> <ul> <li>Proven track record of selling large, complex, multi-site contracts (7–8 figure deals).</li> </ul> <ul> <li>Strong executive presence and ability to engage senior stakeholders for enterprise sales solutioning.</li> </ul> <ul> <li>Expertise in negotiation, RFPs, contracting, pricing strategies, and governance.</li> </ul> <ul> <li>Analytical mindset—comfortable with metrics, forecasting, pipeline management, CRM data.</li> </ul> <ul> <li>Excellent communication, presentation, and storytelling skills.</li> </ul> <ul> <li>Ability to work cross-functionally with operations, marketing, finance, and deliver results in ambiguous, fast-changing environments.</li> </ul> <ul> <li>Bachelor’s degree (MBA or related advanced degree a plus).</li> </ul> <p><strong>Success Metrics (First 6–12 Months)</strong></p> <ul> <li>Establish a qualified enterprise pipeline of target accounts.</li> </ul> <ul> <li>Close anchor enterprise deal(s) — e.g. multi-site contract(s).</li> </ul> <ul> <li>Improve win rates, shorten sales cycle times, and raise deal sizes vs baseline.</li> </ul> <ul> <li>Implement scalable sales processes, playbooks, and tools.</li> </ul> <ul> <li>Achieve assigned deal size in pursuit of $15m+ accounts as a baseline</li> </ul>