Vice President of Operations, Caliber

Vice President of Operations
Caliber Service Management — A Leo Facilities Maintenance Company
Location: Exton, PA (on-site 4+ days/week strongly preferred; exceptional candidates elsewhere considered, with regular travel)    
Reports to: President, Caliber

About Leo Facilities Maintenance
Leo Facilities Maintenance is a premier national facilities maintenance platform within the Orion Group, delivering interior and exterior services across HVAC, plumbing, electrical, handyman, locks & access solutions, onsite building engineers, landscaping, snow, and other exterior services. Since launching in 2022, Leo has assembled 13 operating partnerships generating $380M+ in revenue. Leo’s hybrid model pairs the geographic reach of a vendor-managed network with the white-glove service of a self-perform expert — unlocking cross-sell opportunities for every partner and an unparalleled customer experience.
About Caliber
Caliber Service Management is one of Leo’s cornerstone operating companies — a ~$130M exterior-services business serving multi-site commercial, retail, and industrial customers nationally, with a five-year plan to reach a quarter-billion in revenue. Caliber delivers primarily through a service-provider / vendor-managed model (subcontracted and co-delivery). Its work is concentrated in exterior services — roughly 60% snow removal and 40% landscaping / grounds — an episodic, weather-driven model in which peak season demands relentless, around-the-clock execution. Caliber is now operationalizing adjacent service lines (lot sweeping, stormwater remediation, roofing, and light construction projects). Caliber is the company on which much of Leo’s exterior service model was built; Leo’s CEO, Cecil Moore, came up through the Caliber CEO seat before being promoted to lead the platform. As Caliber continues to scale, the President is hiring a Vice President of Operations to serve as their right hand and the operating engine of the business.

About the Role
We are seeking a driven, results-oriented Vice President of Operations to be the right-hand operator to the President of Caliber and to lead day-to-day execution of a ~$130M facilities maintenance business. You will own service delivery, operational metrics, margin, and customer outcomes across Caliber’s geographies and service lines — delivered through a dispersed network of service providers and field teams. You will translate strategy into action, install operating rigor where it is missing, and unlock the next leg of profitable growth. This is a highly visible leadership role that demands strategic vision, decisive hands-on execution, KPI discipline, and the grit to lead through episodic peak-season demand.

What You’ll Do
•    Serve as the President’s right hand — own the operating cadence, translate strategy into weekly execution, and step in on behalf of the President with customers, FM partners, and the Leo platform team as needed.
•    Own operational P&L drivers: gross margin, cost of revenue / cost of service, work-order economics, and overhead — to plan — and partner with the broader team on EBITDA.
•    Lead service delivery through Caliber’s service-provider / vendor-managed network and field teams; standardize dispatch, scheduling, work-order management, and quality assurance across a dispersed, subcontracted workforce.
•    Install and run a disciplined, KPI-rich operating rhythm — daily huddles, weekly ops reviews, monthly business reviews — covering on-time service, work-order management, quality, safety, gross-margin bridges, and daily-management (“DMB”) stats.
•    Stand up new margin-compression analytics and partner with estimation / pricing to protect and expand margin.
•    Tighten service-to-cash in partnership with Finance — drive a step-change reduction in days-to-invoice and cleaner work-order-to-invoice flow.
•    Own safety as a non-negotiable: ensure compliant field practices, drive measurable improvement, and target zero serious-injury events.
•    Protect and deepen relationships with major FM partners, while supporting Caliber’s diversification into direct customer relationships.
•    Operationalize new service-line adjacencies (lot sweeping, stormwater remediation, roofing, light construction) as Caliber expands its offering.
•    Lead the operations organization — ~4 account directors, regional program operators (RPOs), field teams, and account management, plus estimation / pricing support — hire, onboard, coach, and succession-plan.
•    Lead the business through peak snow season: align capacity, service providers, and field execution to an episodic, weather-driven demand curve.
•    Support integration of tuck-in acquisitions — operating-system rollouts, standardization, and rebadging where applicable.
•    Drive continuous improvement using Leo and Orion’s frameworks (Lean / A3), and embed an ownership mentality across the organization.
•    Own technology adoption across operations — work-order management, dispatch, mobile, and reporting — and ensure clean, audit-ready data.

What Success Looks Like
In this role, you will build a disciplined, scalable operating engine inside a ~$130M field-service business — one that grows revenue, expands margin, converts cash faster, and earns the trust of customers, FM partners, and the Leo platform team.
Measured by
•    Financial performance: Gross-margin attainment vs. plan; cost of revenue / cost of service to target; margin-compression analytics live and informing pricing; EBITDA contribution to plan.
•    Service-to-cash: Step-change reduction in days-to-invoice (target ~10 days of improvement); cleaner work-order-to-invoice flow; DSO improvement.
•    Operational performance: On-time service, work-order management SLAs, quality scores, and dispatch / scheduling productivity across a dispersed workforce.
•    Customer outcomes: No-red / no-risk service scores with JLL and other FM partners; retention and expansion of named accounts; progress diversifying toward direct relationships.
•    Safety: Year-over-year improvement; zero serious-injury events; safety-program adoption across the network.
•    Talent & team: KPIs and a development plan for every direct report; improved retention; a named successor for every key role; successful acquisition integrations.
•    Season execution: A peak snow season delivered admirably — service, safety, and margin held through episodic demand.
If this person is exactly who we hope for, the President of Caliber gains real leverage — able to focus on customers, growth, and Leo platform strategy because operations runs with predictable, repeatable rigor.

What You Bring
Required
•    12–15+ years of progressive operations leadership in commercial / industrial field services — facilities maintenance, exterior services, landscaping / snow, building services, or a closely related multi-site, dispersed-workforce business (10 years is the absolute floor).
•    Formerly has had~$50M+ of operating responsibility; multi-state operations experience.
•    Deep, hands-on understanding of a service-provider / vendor-managed (subcontracted, co-delivery) operating model; self-perform and / or route-based experience is a strong plus.
•    Direct ownership of operational P&L drivers — gross margin, cost of service, work-order economics — with a track record of moving the numbers.
•    Experience standing up or running a disciplined, KPI-rich operating rhythm: daily / weekly / monthly cadence, scorecards, and accountability mechanisms that stick.
•    National-account exposure and customer-facing comfort — able to hold relationships with FM partners (JLL, CBRE, Cushman & Wakefield) and direct accounts.
•    Event-based / episodic operating experience under extreme time pressure (e.g., snow response, peak-season or emergency-response operations) 
•    Track record leading large, distributed, blue-collar teams (100+), improving retention, and integrating acquisitions.
•    Decisive on-site leadership, crisp follow-through, bias to action, and demonstrated extreme ownership.
•    Willingness to be in Exton, PA (strongly preferred) and to travel ~40% across company locations and key customer sites.

Preferred
•    Private-equity-backed or holding-company-backed field-service platform experience; comfort operating within a platform rhythm without losing the OpCo voice.
•    Continuous improvement / Lean background (Six Sigma / black belt, Toyota A3, Kaizen, or equivalent) — certification not required, but real fluency expected.
•    Integration experience — leading operating-system rollouts, standardization, or rebadging in tuck-in acquisitions.
•    Proficiency with field-service technology and dashboarding tools (e.g., work-order / dispatch platforms, Power BI or similar).
•    Bachelor’s degree in Engineering, Operations, Business, or a related field; MBA or equivalent operating credentials a plus.

Compensation
Caliber and Leo Facilities Maintenance determine compensation based on the seniority and scope of the role and the cost of labor. Final compensation will be determined based on a number of factors including job-related knowledge, skills, and experience.

Orion Companies are equal-opportunity employers. We hire for talent, ownership, and character — and we win the right way.