Market Growth Leader Sales & Market Expansion – Insurance Brokerage | The Baldwin Group

The Baldwin Group, a top 15 U.S. insurance brokerage, is seeking a dynamic and proven Director of Sales in the Greater Chicago market—one of the fastest-growing and most competitive markets in the country. This is a rare opportunity to build, scale, and inspire a market-leading team while leveraging the unmatched resources of a national platform with the entrepreneurial spirit of a local leader.

What You’ll Do

• Set & Execute Market Strategy – Develop and implement sales strategies that deliver on aggressive revenue and growth targets, including expanding into new markets and identifying innovative sales channels.
• Build & Elevate a Winning Team – Attract, hire, and develop high-performing sales professionals; coach and mentor advisors to reach peak performance while fostering a culture of accountability and client excellence.
• Drive Client Growth – Manage and deepen key client relationships, identifying opportunities to upsell and cross-sell across Baldwin’s portfolio of insurance solutions.
• Market Leadership – Represent Baldwin across the Chicago business community, strengthening our presence through client engagement, networking, and industry involvement.
• Performance Leadership – Monitor sales performance, provide ongoing feedback, and implement strategies to maximize productivity and outcomes.
• Enable Excellence – Ensure your team has the knowledge, tools, and training to deliver best-in-class client advice, while maintaining compliance with regulatory standards and company policies.
• Collaborate & Integrate – Partner with leaders across Baldwin to align sales initiatives with broader business priorities, ensuring seamless client solutions and market integration.
• Stay Ahead of the Market – Track competitor activity and market trends to refine strategies and keep Baldwin at the forefront of the industry.

What You Bring

• 10+ years of progressive sales leadership experience in the insurance industry.
• A proven track record of building, leading, and retaining top-performing sales teams.
• Demonstrated success driving revenue growth and capturing market share in competitive environments.
• Exceptional leadership, communication, and relationship-building skills.
• Bachelor’s degree required; advanced certifications/designations (CLU, CPCU, CFP) preferred.

Why Join Baldwin Group?

• Lead one of Baldwin’s most strategically important and fastest-growing markets.
• Access the strength of a national platform with the agility and culture of an entrepreneurial firm.
• Competitive base compensation, robust incentive opportunities, and long-term growth potential.
• A values-driven culture built on growth, grit, and “we before me.”

IMPORTANT NOTICE:This position description is intended to describe the level of work required of the person performing in the role and is not a contract. The essential responsibilities are outlined; other duties may be assigned as needs arise or as required to support the organization. All requirements may be subject to reasonable accommodation to applicants and colleagues who need them for medical or religious reasons.

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The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.