Chief of Staff, Growth & Execution

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

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,