Chief Operating Officer

Location: Chicago, IL (Hybrid)

Compensation: $225k - $275k base salary + Benefits

Position Overview:

Our client, a dynamic and growth-oriented boutique wealth management firm, is seeking an experienced Chief Operating Officer to serve as the operational leader and integrator of the business.

Working closely with firm ownership and the executive leadership team, the COO will translate long-term vision and growth objectives into disciplined execution. This individual will be responsible for aligning people, processes, and performance while building the operational infrastructure needed to support the firm's continued growth.

This is not a traditional corporate COO role. It is a hands-on leadership opportunity within an entrepreneurial, high-accountability environment. The right leader will be comfortable stepping into ambiguity, creating structure where it does not yet exist, respectfully challenging the status quo, and bringing clarity, accountability, and momentum to a growing organization.

Key Responsibilities:

Strategic & Operational Leadership:

• Partner directly with firm ownership and the executive leadership team to translate strategic vision into clear priorities and execution
• Lead and oversee operational functions across the organization, ensuring alignment between teams and departments
• Implement and drive operating systems, including EOS/Traction or similar frameworks
• Establish clear KPIs, accountability structures, and performance management processes
• Identify opportunities to improve operational efficiency, scalability, and execution while maintaining an exceptional client experience
• Create structure, processes, and systems that support the firm's continued growth
• Support M&A diligence and integration initiatives as needed

Financial, Compliance & Risk Oversight:

• Oversee financial management in partnership with firm ownership, including budgeting, performance tracking, and operational reporting
• Use financial and operational data to identify trends, opportunities, and areas requiring attention
• Lead compliance oversight and risk management processes
• Ensure operational decisions support both the firm's growth objectives and long-term sustainability

Leadership & Team Development:

• Build leadership depth across the organization by coaching and developing managers and emerging leaders
• Establish clear expectations and hold leaders and team members accountable to agreed-upon priorities
• Influence outcomes across the organization, including with senior leaders and firm partners
• Make difficult personnel decisions when necessary while maintaining strong cultural and performance standards
• Serve as a trusted counterbalance to ownership, with the confidence to respectfully challenge assumptions and push back when appropriate
• Lead the organization through change with clarity, empathy, and decisiveness
• Strengthen communication, alignment, and accountability across teams

Qualifications:

• 10+ years of leadership experience within financial services, wealth management, insurance, or a related professional services environment
• Proven experience helping grow and scale an organization
• Demonstrated success leading operations within an entrepreneurial or growth-oriented business
• Experience operating within or implementing EOS/Traction or a similar operating framework preferred
• Strong financial acumen with experience managing budgets, performance metrics, and operational reporting
• Demonstrated ability to lead multi-level teams and develop other leaders
• Strong strategic thinking paired with the ability and willingness to execute at a hands-on level
• Proven ability to create structure, accountability, and consistency within a growing organization
• Strong communication, decision-making, and problem-solving skills
• Ability to influence senior leaders and confidently navigate difficult conversations
• Clean compliance record

What We're Looking For:

The ideal candidate is a confident, steady, and highly accountable leader who thrives in an entrepreneurial environment. This person is comfortable operating without a perfect playbook and has the ability to turn ambiguity into structure, priorities, and action.

They will bring a strong combination of strategic thinking and operational execution. Rather than simply maintaining existing processes, this leader will identify what needs to change, build better systems, and hold the organization accountable to following through.

Just as importantly, the COO must be an effective partner to ownership—someone who understands and supports the firm's vision while bringing an independent perspective, asking difficult questions, and respectfully pushing back when necessary.

What Success Looks Like:

Within the first 18–24 months, the Chief Operating Officer will have:

• Brought greater clarity and structure to firm-wide priorities
• Strengthened accountability across partners, leaders, and team members
• Improved operational efficiency and scalability
• Enhanced leadership capabilities throughout the organization
• Built stronger systems and processes to support continued growth
• Created additional capacity for ownership to focus on growth, vision, and client impact

This is an opportunity for a proven operational leader who is energized by building structure within a growth-stage firm and values partnership, accountability, and long-term impact over corporate hierarchy.