Case Study: How Sizemore Built a Modern Sales Engine and Unlocked Its Next Era of Growth

“Chief Outsiders stood up the business development structure needed to build a brand-new sales origination function at Sizemore. The work they did allowed us to invest with more clarity and confidence and has set us up for continued organic growth.”

Aashish Chaturvedi, Vice President, Operations, Inspirit Equity 

Sizemore, Inc., a third generation facility services company, had grown to roughly $135 million in revenue without ever having a formal sales or marketing organization. With 74% of revenue concentrated in a single client and a future ownership transition underway, leadership engaged Chief Outsiders Fractional Chief Revenue Officer (CRO), Dave MacIntosh, to build a modern revenue engine. Over eight months, MacIntosh strengthened valuation ahead of acquisition by Inspirit Equity, delivered a complete sales infrastructure, recruited Sizemore’s first VP of Sales, and repositioned the pipeline upmarket.

Business Background

Strong Reputation Drives Organic Growth

Founded in 1955, Sizemore, Inc. built a strong reputation across janitorial, security, and industrial staffing services. For decades, the company grew organically through relationships, referrals, and operational excellence.

“Our growth has been organic through word of mouth,” CEO Preston Sizemore explained. “We did not have a sales infrastructure, a sales department, or organization.” Despite exceeding $130 million in revenue, Sizemore had never developed a formal sales function or go‑to‑market strategy.

A Family Business at an Inflection Point

The pandemic accelerated Sizemore’s growth dramatically. Amazon’s rapid expansion of distribution centers scaled Sizemore from $40 million to $135 million in just a few years. But the surge created a new challenge: 74% of revenue was now tied to one client.

“We were 70% Amazon,” Preston said. “We wanted to diversify our client base.” The company’s leadership recognized that concentration risk threatened both stability and valuation.

At the same time, Sizemore faced a generational transition. With no fourth‑generation successor and increasing pressure to modernize, the company began exploring private equity investment.

Choosing the Right Partner

Seeking to address the sales challenges, Sizemore’s CFO, a Vistage member, introduced leadership to Chief Outsiders. About going outside the company, Preston Sizemore recalled how difficult it had been to build a recruiting team internally: “It was painful. We didn’t want to repeat that with sales.”

Chief Outsiders presented several candidates, but Fractional CRO Dave MacIntosh stood out immediately. “Culturally, I thought he fit our organization,” Preston Sizemore said. “He impressed everyone with his approach and knowledge.”

MacIntosh’s background in facility services, private equity environments, and revenue transformation made him uniquely equipped to guide Sizemore through both sales modernization and acquisition readiness.

Strategy

Architecting Sizemore’s First Revenue Organization

MacIntosh began with a full field assessment, stakeholder interviews, and a deep dive into Sizemore’s operations. He quickly identified the core challenge:

“No sales strategy, no sales plan, no growth strategy existed,” Preston Sizemore explained. “Fundamental building blocks were missing.” The company lacked ICPs, sales stages, qualification criteria, proposal templates, CRM structure, compensation plans, and performance management.

Working on-site and remotely with leadership, he designed and executed a comprehensive, multi‑workstream plan:

1. Sales Strategy & Foundation - Developed Sizemore’s first formal go‑to‑market strategy, including ICPs, competitive positioning, value propositions, and revenue targets by service line and geography. Mapped the company’s growth path toward $175 million, aligning strategy with operational capacity and diversification goals.
2. Sales Process & Methodology - Built a standardized stage‑gate sales process with clear entry/exit criteria, qualification frameworks, objection‑handling guidance, and proposal templates. He also optimized HubSpot CRM to match the new workflow, enabling pipeline visibility.
3. Talent & Team Development - Defined sales roles, competencies, and compensation plans. Created a complete onboarding program and training curriculum then led recruitment of Sizemore’s first VP of Sales using OMG sales aptitude assessments and a boutique recruiting partner.
4. Implementation & Optimization - Launched cross‑selling programs, outbound prospecting frameworks, and performance dashboards. Established weekly sales meetings, coaching rhythms, and reporting cadence.
5. Sustainability & Handoff - MacIntosh delivered a 100‑day plan for the new VP of Sales and documented all processes, systems, and institutional knowledge to ensure continuity.

Total Addressable Market (TAM) of $144 billion

Among the many insights MacIntosh gathered and prepared, his TAM analysis helped Sizemore understand the scale of opportunity beyond Amazon and guided ICP development and diversification strategy.

Building the Infrastructure Sizemore Never Had

Preston Sizemore described the transformation: “Dave built long‑lasting value from what he gave us—guidelines, step‑by‑step processes, the sales process, onboarding, compensation, assessments—that we continue to use going forward.”

MacIntosh’s work included:

• Designing ICPs across all service lines
• Mapping revenue targets by geography and industry
• Creating compensation plans that aligned incentives with diversification
• Implementing HubSpot as the central CRM
• Building proposal templates and sales enablement tools
• Establishing KPIs, dashboards, and reporting cadence
• Leading recruitment of the VP of Sales through a boutique firm he trusted

Recruiting and Onboarding the VP of Sales

MacIntosh led a rigorous recruitment process, using OMG sales aptitude assessments and a specialized recruiting partner. “We did not want someone just off LinkedIn,” Preston Sizemore said. “We wanted a veteran from our industry.” That search produced Josh Nelson, who joined Sizemore as its first VP of Sales.

“Josh knew what our ideal prospect looked like,” Preston Sizemore related. “He and Dave had many conversations. He needed to get up to speed quickly—and he did.”

Supporting Private Equity Due Diligence

During the engagement, Sizemore was acquired by Inspirit Equity. Hence, MacIntosh integrated PE reporting cadence, briefed operating partners, and supported diligence for a subsequent bolt‑on acquisition.

Aashish Chaturvedi, Vice President, Operations at Inspirit Equity noted: “Dave did a great job outlining the work his team had done prior to my involvement, which gave me the information I needed to get up to speed and understand what it would take to effectuate change.”

“And the materials he prepared were critical to onboarding and ensuring the new VP of Sales could hit the ground running.”

Results

Modern Sales Engine and Immediate Growth

With the new sales infrastructure in place, Sizemore grew from $135 million toward a $155 million run rate, on pace to reach its $175 million target. “Some of that is organic growth,” MacIntosh noted, “but the pipeline is repositioned upmarket.” ICP refinement increased average target account value from $220K to $1.1 million—a five‑fold improvement.

Nelson, onboarded 30–60 days ahead of schedule, immediately began building his Sales team, securing early wins, and executing the onboarding plan MacIntosh designed.

Cross‑Functional Impact

MacIntosh’s work extended beyond sales. Marketing gained clarity on ICPs and messaging; HR adopted the compensation and onboarding frameworks; and Operations benefited from proposal validation processes and improved coordination with sales.

“He left us a playbook,” Preston Sizemore emphasized. “We use it not just for sales, but in other areas of our business.”

Strengthened Valuation for Acquisition

Preston Sizemore emphasized the impact of MacIntosh’s work on the Inspirit Equity acquisition: “When you look at our value when we were being acquired, the roadmap Dave put together had a positive impact. We could show how we’d accelerate growth, diversify, and meet targets.”

“As a long‑term investor, we needed confidence that Sizemore could grow sustainably,” added Chaturvedi. “Chief Outsiders gave us clarity on the sales function, market sizing, and ideal customer profiles. It set us up for continued organic growth.”

A Sustainable Path Forward

“Chief Outsiders stood up the business development structure needed to build a brand-new sales origination function at Sizemore,” concluded Chaturvedi. “The work they did allowed us to invest with more clarity and confidence and has set us up for continued organic growth.”

“Bottom line, they built an entire sales organization for us,” added CEO, Preston Sizemore. “Not just hiring the right leader but building the infrastructure and leaving us a roadmap for the future.”