Director of Operations

Company

Our client is a well-established leader in exterior building maintenance, serving premier office, multifamily, retail, hospitality, mixed-use and specialty-use properties primarily in the Chicago CBD. With a strong reputation built over decades, the company is known for its operational excellence, safety-first culture, and consistent delivery of high-quality service across complex and high-profile environments.

The organization specializes in comprehensive building care, leveraging advanced equipment, proven methodologies, and highly trained teams to service properties of all sizes. Their success is driven by customized service solutions, disciplined execution, and a commitment to long-term client relationships.

As a large, union-based operation, our client places a strong emphasis on workforce development, rigorous safety training, and clear communication at every level of the organization. They foster a collaborative, performance-oriented culture where accountability, responsiveness, and attention to detail are core expectations. The company is already a local market leader and is well-positioned for continued growth and operational scale.

Position

The Director of Operations will be a key member of the executive leadership team, responsible for overseeing and optimizing all field operations, service delivery, equipment maintenance, safety, and labor execution across the organization. This role will partner closely with ownership and senior leadership to translate strategic objectives into disciplined, scalable operational performance.

The ideal candidate is a hands-on, metrics-driven operator with experience leading complex, labor-intensive service organizations. The Director of Operations will be accountable for driving consistency, efficiency, and profitability while preserving the company’s strong culture and reputation for service excellence.

This is a rare opportunity to step into a high-impact leadership role within a respected, established company that combines operational complexity with significant growth potential. The Director of Operations will have meaningful influence over the organization’s next phase of scale, professionalization, and long-term success.

Responsibilities

• Lead and oversee all operational functions, including field operations, human resources, service execution, scheduling, safety, labor management, and quality control.
• Direct the organization’s efforts in achieving financial goals, objectives, and budgets with focus on setting measurable goals and insuring accountability.
• Develop and implement scalable operational systems, processes to support growth while maintaining service standards
• Ensure personnel policies and procedures are appropriate for the effective and efficient functioning within the working environment and the protection of staff and adjust as necessary
• Encourages and facilitates the application of industry best practices and technology to enable the re-engineering of policies, programs, and processes to make optimal use of resources.
• Set company-wide objectives and performance metrics (KPIs); ensure regular, cross-departmental communication focused on efficient and profitable operations. Utilize industry benchmarks to track results and identify growth opportunities and priorities. Establish processes for internal accountability, prioritization, and successful execution across all segments of the business.
• Develop annual budgets, drive operational efficiency, margin improvement, and cost discipline across all service lines.
• Oversee supply inventory management and review, recommend and approve the firm’s capital expenditures above a certain threshold.
• Ensure compliance with union agreements, OSHA and other safety regulations, and company policies, while fostering positive labor relations.
• Partner with sales and client-facing teams to ensure seamless onboarding, execution, and retention of key accounts.
• Negotiate and approve major service contracts and review and approve smaller service contracts delegated to subordinates.
• Build, mentor, and develop managers and subordinates, creating clear accountability and development across all disciplines within the organization.
• Track crew productivity, job quality, and customer feedback.
• Champion a safety-first focus across all disciplines, ensuring training, protocols, and risk management practices are consistently executed. Preserve and enhance company culture, with a focus on employee engagement and development; conduct regular performance reviews of direct reports
• Provide data-driven insights and reporting to ownership and senior leadership to support strategic decision-making

Qualifications

• A seasoned, senior operations leadership executive (Director, VP of Operations, Chief Operating Officer or equivalent) with a minimum of 10 years of experience in property management and/or a labor-intensive, service-based organization, ideally serving commercial property clients and/or site-level experience in a building services role.
• Significant experience with bids, request for proposals (RFPs), contracts, and operational pricing.
• Ability to review service, vendor and other contracts.
• Deep understanding of safety, compliance, and regulatory oversight.
• Supervises hiring, I9 compliance, and all other government requirements.
• Experience working directly with inspectors, regulators, union leadership, and municipal agencies.
• Demonstrates understanding of insurance issues and risk management.
• Experience handling unemployment and worker’s compensation claims.
• Experience working within union or highly regulated labor environments.
• Experience with MBE (Minority Business Enterprise)/WBE (Women Business Enterprise) requirements.
• Ability to analyze financial statements and have a strong understanding of operational metrics, process improvement, and scalable execution.
• Experience testifying in legal and administrative proceedings.
• Knowledge of OSHA standards across all operations, including hazard communication, PPE requirements, recordkeeping (OSHA 300/300A), and incident reporting.
• Demonstrated success managing large, distributed field teams and complex scheduling environments.
• Hands-on leadership style with the ability to balance strategic vision and day-to-day execution.
• Proven ability to build structure, accountability, and performance standards without disrupting culture.

Personal Skills & Attributes

• Strong operational judgment with a pragmatic, common-sense approach to decision-making.
• Calm, steady presence under pressure; effective in high-stakes and time-sensitive situations.
• Clear, direct communicator able to influence ownership, executives, union leaders, and field managers.
• High integrity, credibility, and trustworthiness; consistently follows through on commitments.
• Resilient and persistent; thrives in demanding, labor-intensive environments.
• Strong safety-first mindset with deep respect for compliance, training, and risk management.
• Demonstrated expertise in verbal and written communications.