Chief Operating Officer

Location: Chicago, IL

Compensation: Base $175K-$250K (DOE) + Performance Bonuses

Who We Are: Established personal injury law firm headquartered in Chicago attaining over $20M in annual revenue.

Position Overview: We are seeking an experienced, strategic Chief Operating Officer to lead and scale day-to-day operations across our organization. The COO will partner with senior leadership to translate strategy into measurable operational plans, optimize processes and systems (including Salesforce and MSO platforms), and drive growth through efficient operations, SOP development, vendor management, and lead generation and retention programs.

Key Responsibilities: Develop and execute operational strategies that align with company goals and support scalable growth. Own and continuously improve core operational processes and SOPs to increase efficiency, consistency, and quality across functions. Lead and mentor operations, sales operations, customer success, and support teams to meet KPIs and deliver exceptional customer outcomes. Oversee Salesforce implementation, configuration, and adoption to ensure accurate pipeline management, reporting, and operational automation. Design, implement, and manage lead generation and lead retention programs in partnership with marketing and sales to optimize conversion and lifetime value. Manage vendor selection, contracts, and performance to ensure cost-effective, high-quality service delivery and strong partner relationships. Establish and monitor operational metrics, dashboards, and regular reporting to the executive team; use data to drive decisions and continuous improvement. Direct MSO (Management Services Organization) or equivalent shared services functionsensuring service-level agreements, compliance, and integration with business units. Partner with Finance to manage budgets, forecasts, and resource allocation tied to operational initiatives and efficiencies. Drive cross-functional initiatives to remove operational bottlenecks, streamline handoffs, and improve customer experience and retention. Champion a culture of accountability, operational excellence, and continuous improvement; hire and develop high-performing teams. Lead risk management, regulatory compliance, and operational readiness for new products, markets, or major initiatives.

Qualifications: 7+ years of progressive operations leadership experience; prior COO, Head of Operations, or VP-level experience strongly preferred. Bachelors degree required; MBA or advanced degree preferred. Proven experience with Salesforce administration/use cases and leveraging CRM data to drive operational improvements and sales effectiveness. Hands-on experience creating, documenting, and enforcing SOPs across multiple teams and geographies. Experience managing or partnering with an MSO or shared services organization is highly desirable. Demonstrated success designing and optimizing lead generation and lead retention strategies that materially improve pipeline and revenue retention. Strong vendor management experience, including contract negotiation, SLAs, and performance oversight. Data-driven mindset with experience using KPIs, dashboards, and analytics tools to inform decisions and measure impact. Exceptional leadership, communication, and stakeholder management skills; ability to influence at all levels of the organization. Comfortable operating in fast-growing, ambiguous environments and leading change initiatives while maintaining operational excellence.

Base Salary: $175K-$250K (DOE)