Head of Enterprise Sales, Leo FM

Leo FM

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.).

We’re scaling rapidly and looking for a seasoned enterprise sales leader to drive large, complex deals with major commercial, institutional, and national accounts.

Role Overview

As Head of Enterprise Sales, 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.

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.

Key Responsibilities

• Build, refine, and execute a go-to-market strategy for enterprise accounts (national chains, multi-site portfolios, institutional clients).

• Forecast pipeline and revenue, set targets, monitor sales metrics (win rates, sales cycles, average deal size, churn, etc.).

• Own and manage large, multi-site, multi-year RFPs and contract negotiations with senior stakeholders (C-suite, facility directors).

• Collaborate with marketing, operations, service delivery, and finance to build compelling proposals, pricing models, value propositions, and support the full sales lifecycle.

• Drive customer relationship management at the executive level, upsell / cross-sell opportunities, renewals, and account expansion.

• Analyze market trends, competition, pricing, and product mix to refine positioning and differentiate Leo FM’s offering.

• Develop scalable processes, tools, sales enablement resources, and operational rigor to support growth.

• Report regularly to executive leadership on sales performance, forecasts, risks/opportunities, and strategic insights.

Required Experience & Skills

• 15+ years of enterprise B2B sales experience, ideally in facility services, facilities management, building services, real estate services, or a related services industry.

• Proven track record of selling large, complex, multi-site contracts (7–8 figure deals).

• Strong executive presence and ability to engage senior stakeholders for enterprise sales solutioning.

• Expertise in negotiation, RFPs, contracting, pricing strategies, and governance.

• Analytical mindset—comfortable with metrics, forecasting, pipeline management, CRM data.

• Excellent communication, presentation, and storytelling skills.

• Ability to work cross-functionally with operations, marketing, finance, and deliver results in ambiguous, fast-changing environments.

• Bachelor’s degree (MBA or related advanced degree a plus).

Success Metrics (First 6–12 Months)

• Establish a qualified enterprise pipeline of target accounts.

• Close anchor enterprise deal(s) — e.g. multi-site contract(s).

• Improve win rates, shorten sales cycle times, and raise deal sizes vs baseline.

• Implement scalable sales processes, playbooks, and tools.

• Achieve assigned deal size in pursuit of $15m+ accounts as a baseline