Chief Operating Officer

NOTE:

This is a Chicago-based role, not remote.

Mainland is a 18-year growth-focused marketing and public relations agency serving franchise and multi-unit brands. We specialize in disciplined storytelling, performance-driven strategy, and operational excellence.

As we scale, we are strengthening our leadership spine and building a more institutional, execution-driven organization. We are hiring a Chicago-based Chief Operating Officer to anchor in-office leadership, elevate performance, and protect execution across the company.

This is not a symbolic COO role. This is an execution and accountability role.

The COO will serve as the Integrator of the organization — translating vision into execution and ensuring performance standards are upheld across all portfolios and delivery teams.

• Delivery team execution (PR, Content, Digital)
• Recruiting and talent development
• Operational systems and infrastructure
• In-office leadership culture

The CEO focuses on vision, growth, partnerships, and strategy. You own execution.

• Directly manage Portfolio Leads and Operations Managers
• Run weekly executive KPI reviews
• Enforce standards around deadlines, scope, and performance
• Address underperformance quickly and professionally
• Build leadership density in the Chicago office
• Monitor revenue and margin performance by portfolio
• Ensure client retention and service consistency
• Identify growth and risk areas early
• Protect scope discipline and delivery predictability

• Oversee PR, Content, and Digital performance
• Ensure capacity planning and workflow discipline
• Implement systems that eliminate recurring operational breakdowns
• Own leadership hiring process
• Build structured onboarding and 30-60-90 plans
• Develop high performers and address low performers

• Strengthen internal systems (Accelo and reporting dashboards)
• Improve process clarity and cross-team communication
• Eliminate inefficiencies and unnecessary founder dependency

• Deadlines are consistently met
• High performers feel supported and elevated
• Underperformance is addressed swiftly
• Founder is removed from day-to-day enforcement
• Chicago office becomes the leadership center of gravity

• 8+ years leading operations in a professional services, agency, or consulting environment
• Experience managing 25–75 person teams
• Strong track record of enforcing accountability without creating drama
• Comfortable having difficult performance conversations
• Operationally disciplined and systems-oriented
• High emotional intelligence with strong backbone
• Comfortable working in-office 3+ days per week (Chicago-based required)

Experience in agency, marketing services, or franchise-related industries is strongly preferred.

Competitive executive compensation aligned with experience.

Performance-based incentives tied to company growth and margin improvement.

This is a pivotal hire. We are building an institutional firm — one that performs consistently whether the founder is in the room or not. If you are energized by structure, clarity, accountability, and building high-performing teams — we want to speak with you.