Executive Regional Director, Midwest

Job Title

Executive Regional Director, Midwest

Job Description Summary

The Executive Regional Director is a senior leadership responsible for driving regional performance, strengthening market leadership, and ensuring consistent execution of the firm’s brokerage, operational, and growth strategies. This role serves as the senior business leader for the region and managing principal for the Chicago territory, balancing revenue growth, talent leadership, client relationships, and operational discipline while partnering closely with corporate functions.

The Executive Regional Director is expected to lead with a strong commercial mindset, act as a trusted advisor to top producers and market leaders and represent the firm externally with clients and industry partners.

Job Description

Key Responsibilities:

Regional Leadership & Strategy

• Own overall business performance for the region, including revenue growth, profitability, and market expansion.
•  Translate firmwide strategy into clear regional priorities and execution plans.
• Partner with senior leadership to identify growth opportunities, new markets, and strategic investments.
• Ensure consistent application of firm standards, policies, and operating models across the region.

Revenue & Brokerage Performance

• Drive top-line performance through broker productivity, client expansion, and new business development.
• Partner with senior brokers and market leaders on major pursuits, key client relationships, and complex transactions.
• Monitor pipeline, forecasting, and performance metrics, address gaps proactively.
• Support pricing, fee strategy, and deal structuring in partnership with finance and legal.

Talent Leadership & Succession 

• Lead, develop, and retain high-performing regional and market leaders.
•  Oversee recruitment, onboarding, and integration of senior brokers and leadership hires.
•  Champion performance management, coaching, and succession planning across the region.
• Address performance issues decisively and consistently, in partnership with HR and legal.

Client & Market Presence 

• Serve as a visible senior representative of the firm in the region.
•  Build and maintain executive-level client relationships and industry partnerships.
• Represent the firm at key client meetings, industry events, and community engagements.
• Strengthen the firm’s brand, reputation, and competitive positioning in the market.

Operational & Financial Oversight

• Partner with operations, finance, HR, and legal to ensure effective business execution.
• Oversee regional budgeting, expense management, and financial performance.
• Identify operational risks and implement controls to support sustainable growth.
• Ensure compliance with regulatory, legal, and firm requirements.

Knowledge & Experience

• Bachelor’s degree required. An MBA or other advanced degree with real estate or operations concentration is highly desirable.
• 15+ years of experience in commercial real estate brokerage or related services, with senior leadership responsibility.
• Demonstrate ability in leading, motivating and inspiring diverse work teams.  Be fluent in the language and principals of institutional investment real estate.

• Strong credibility in the local market, with the ability to recruit and retain key talent.

• Proven track record of leading large, complex teams and delivering sustained revenue growth.
• Strong understanding of brokerage economics, compensation structures, and deal dynamics.
• Demonstrated ability to influence senior producers and leaders without direct authority.
• Experience managing P&L responsibility and regional financial performance.

Leadership Attributes

    •    Commercially astute with a strong bias toward execution.

    •    Credible, confident, and able to operate effectively with top producers.

    •    Strategic thinker who can also dive into details when needed.

    •    Direct, fair, and consistent in decision-making.

    •    Collaborative leadership style with strong cross-functional partnership skills.

Cushman & Wakefield also provides eligible employees with an opportunity to enroll in a variety of benefit programs, generally including health, vision, and dental insurance, flexible spending accounts, health savings accounts, retirement savings plans, life, and disability insurance programs, and paid and un