Senior Sales Executive, Executive Consulting

Executive Benefits & Risk Management Consulting

Chicago, IL | Hybrid

Our client is a well-established employee benefits and risk management consulting firm serving organizations throughout the Chicago market. For decades, they have partnered with businesses to reduce healthcare costs, improve employee benefits, strengthen workforce strategies, and help organizations make smarter financial decisions regarding one of their largest operating expenses—their people.

Unlike traditional insurance brokerages that simply market insurance products, this organization serves as a trusted advisor to executive leadership teams. Their consultants work directly with CEOs, Presidents, CFOs, business owners, and senior HR leaders to develop customized employee benefits strategies that improve employee satisfaction while reducing long-term costs.

As the organization continues to grow, they are investing in experienced business development professionals who can cultivate executive relationships, identify new opportunities, and build long-term books of business throughout the Chicago market.

This position follows a hybrid work schedule with one in-office collaboration morning each week and the remainder of your time spent meeting with clients and prospects throughout the Chicago market.

You’ll enjoy significant autonomy in planning your territory, developing your business strategy, and managing your schedule while receiving the support of experienced consulting and client service teams.

This is far more than a traditional sales role.

You’ll be joining an organization where you’ll build a recurring book of business rather than chasing one-time transactions. The company provides extensive operational and client service support, allowing you to remain focused on developing relationships and growing your business.

The role offers significant autonomy, direct access to executive leadership, and the opportunity to build a long-term consulting practice with exceptional earning potential.

Successful consultants aren’t simply selling insurance—they’re helping organizations solve complex business challenges while becoming trusted advisors to executive leadership teams.

As a Senior Sales Executive, you’ll be responsible for identifying and developing new business opportunities throughout the Chicago market. You’ll build relationships with executive decision-makers, uncover organizational challenges, and introduce consultative solutions that improve employee benefits while helping companies manage costs and risk.

This is a highly consultative sales environment where success comes from asking thoughtful questions, understanding a client’s business objectives, and positioning yourself as a long-term strategic partner rather than simply another vendor.

You’ll collaborate closely with experienced consulting and service teams throughout the sales process while building your own recurring book of business.

• Develop new business opportunities throughout the Chicago market
• Prospect and cultivate relationships with companies ranging from approximately 100 employees to large enterprise organizations
• Meet with CEOs, Presidents, CFOs, HR executives, and business owners to understand organizational objectives and workforce challenges
• Introduce employee benefits, risk management, and human capital consulting solutions
• Conduct executive discovery meetings and identify opportunities to reduce costs and improve employee benefit strategies
• Build and maintain a robust pipeline of qualified opportunities
• Network throughout the local business community and attend professional events
• Partner with internal consulting specialists during solution development and implementation
• Maintain long-term client relationships that generate recurring revenue year after year

Rather than offering a single product, you’ll introduce organizations to a comprehensive portfolio of consulting services, including:

• Employee Benefits Consulting
• Wellness Programs
• Executive Benefits Planning
• Life & Disability Insurance
• Retirement & Financial Wellness Solutions
• Human Capital Consulting
• Cost Containment…