Chief of Staff

The Chief of Staff Association; Chicago (IL); Hybrid; USD 200,000 - 225,000; Full time

Job summary

The Chief of Staff Association in Chicago seeks a high‑impact Chief of Staff to partner with the CEO and lead cross‑functional initiatives that drive revenue growth and EBITDA expansion. This full‑time, hybrid role reports to the CEO and sits with the executive leadership team to align priorities and ensure disciplined execution.

You will own key workstreams, build reporting dashboards, manage investor communications, and design change programs across go‑to‑market, ops, logistics, and pricing,

Qualifications

• 8+ years of professional experience with time in operating roles within scaling organizations.
• Background in go-to-market, revenue operations, marketplace strategy, logistics, or related disciplines preferred.
• Experience in a PE-backed, high-growth, or venture-backed environment with measurable outcomes.
• Prior Chief of Staff experience is valued but not required.
• Strong analytical and problem-solving capabilities with structured thinking.
• Excellent written and verbal communication skills, with experience supporting executive and board-level audiences.
• High attention to detail, proactive, and ownership mindset.
• Startup experience preferred; must be based in the Chicago area and able to work onsite 3x/week.

Responsibilities

• Serve as a direct execution partner to the CEO—own deliverables end-to-end and help the team prioritize and execute value-creation initiatives across the business.
• Establish and manage a consistent operating cadence across the leadership team, including structured reviews of key initiatives and accountability mechanisms.
• Translate the value creation plan into trackable workstreams; surface risks and issues to leadership.
• Step into functional gaps across go-to-market, operations, logistics analytics, and/or pricing—bringing structure, momentum, and follow-through.
• Build and own reporting dashboards and scorecards for real-time visibility into performance.
• Develop and maintain sponsor reporting materials, board decks, and investor updates with narrative and detail.
• Monitor performance against plan and identify early risk signals with corrective actions.
• Leverage tools and automation to enhance performance tracking and reporting.

Skills

Analytical thinking

Problem solving

Strategic execution

Communication skills

Ownership mindset

Job description

Our client is a technology-enabled roadside assistance, accident management, and vehicle logistics platform serving insurers, OEMs, fleets, and mobility providers across the United States. Over the past decade, the company has built the most advanced fully digital roadside logistics platform in the industry, replacing legacy call-center dispatch with real-time, AI-driven provider matching that delivers faster service, greater transparency, and a superior experience for motorists and enterprise partners alike.

Recently acquired by a Chicago-based private equity firm and simultaneously combined with a strategic add-on acquisition, the company is now led by a team of former executives from a leading logistics marketplace business. With detailed action plans across go-to-market, operations, and technology already in place, the company is now in execution mode with an exciting growth mandate.

About the Role

Our client is seeking a Chief of Staff who will report to the CEO and partner closely with the executive leadership team to drive the execution of strategic initiatives across the business that directly impact revenue growth, EBITDA expansion, and enterprise value. The role serves as a central execution layer, ensuring alignment, accountability, and disciplined follow-through on the company’s highest-priority objectives.

The ideal candidate is a proven chief of staffwith a strong blend of strategic thinking, operational execution, and program leadership. They bring a high level of attention to detail, sound judgment, and critical thinking. They are comfortable navigating ambiguity, managing change, and solving complex problems in a highly collaborative environment startup environment, with a consistent bias toward action and results.

This will be a full-time position based in Chicago (hybrid work environment).

Responsibilities

• Serve as a direct execution partner to the CEO - own deliverables end-to-end and help team prioritize and execute value creation initiatives across the business
• Establish and manage a consistent operating cadence across the leadership team, including structured reviews of key initiatives and accountability mechanisms
• Translate the value creation plan into trackable workstreams; proactively surface risks and issues to leadership
• Step into functional gaps as needed across go-to-market, operations, logistics analytics, and/or pricing - bringing structure, momentum, and follow-through

Performance Management & KPI Ownership:

• Build and own reporting dashboards and scorecards that provide clear, real-time visibility into business performance
• Develop and maintain PE sponsor reporting materials, board decks, and investor updates - responsible for the narrative and the detail
• Monitor performance against plan, identify early risk signals, and recommend corrective action
• Leverage tools and automation to enhance performance tracking, streamline reporting, and enable faster, data-driven decision making across the organization

Cross-Functional Program Leadership:

• Lead high-impact cross-functional initiatives - including ongoing integration workstreams with clearly defined milestones, ownership, and accountability
• Drive GTM execution as needed: support incentive compensation design, sales cadence, and CRM utilization
• Serve as an extension of the CEO across the organization - influencing and aligning a fast-moving leadership team without direct authority
• Design and implement change management strategies to support adoption of new processes and tools
• Identify opportunities to improve operational efficiency and effectiveness across the organization
• Develop and standardize playbooks, templates, and best practices aligned to the company’s operating model

Executive Communication & Stakeholder Engagement:

• Prepare and refine executive presentations, board materials, and external communications on behalf of the CEO
• Act as a liaison between the CEO, the leadership team, and PE team - ensuring alignment on priorities, progress, and strategic direction
• Support organizational change management as new systems, processes, and structures are implemented

Recommended Minimum Qualifications

• 8+ years of professional experience with meaningful time in operating roles within scaling organizations
• Background in go-to-market, revenue operations, marketplace strategy, logistics, or related disciplines preferred
• Experience in a PE-backed, high-growth, or venture-backed environment where accountability was tied to measurable outcomes
• Prior Chief of Staff experience is valued but not required
• Strong analytical and problem-solving capabilities with structured thinking
• Excellent written and verbal communication skills, with experience supporting executive and board-level audiences
• High attention to detail, proactive, and strong ownership mindset
• Ability to operate effectively in fast-paced, ambiguous environments (startup experience preferred)
• Must be based in the Chicago area and able to work onsite 3x/week (Bucktown/West Lincoln Park area)

Compensation Range: DOE $200-225K/yr Base Compensation + Bonus + competitive benefits package

What to Expect from Our Selection Process

This search is being conducted on a retained basis by CSA Talent, an executive search firm specializing in Chief of Staff placements. Candidates can expect the following process:

• CSA screening and behavioral assessment (+ Predictive Index)
• Initial interview with the CEO
• Interview with PE firm
• Case study
• Final in-person interview with the CEO and senior leadership team

Our client is committed to creating and maintaining a diverse and inclusive workplace where our employees can thrive and be themselves! We welcome all persons into our community. We embrace the diversity of gender, gender identity or expression, race, color, religious creed, national origin, ancestry, age, physical and mental disabilities, medical condition, genetic characteristic, sexual orientation, marital status, family care or medical leave status, military or veteran status, or perceived membership in any of these groups.