Client Executive - Employee Benefits

Hylant Group, Inc.; Chicago (IL); On-site; USD 90,000 - 130,000; Full time

Job summary

Hylant Group, Inc. in Chicago seeks a Client Executive to grow and manage a book of business in the Chicago Benefits market. You will retain current clients while proactively identifying new opportunities and leveraging Hubspot to track activities and renewals.

You will develop sales plans, build relationships with clients, and collaborate with internal teams to provide tailored Hylant solutions. Travel for meetings and industry events is expected as part of the role.

Qualifications

• 4-5 years of proven insurance brokerage sales experience.
• Hold and maintain active Life & Health License.
• Intermediate Microsoft Office skills (Excel, Word, PowerPoint, Outlook).
• Exceptional oral and written communication skills.

Responsibilities

• Develop and grow a client book of business in the Chicago Benefits market.
• Establish sales development plans to originate business with new clients.
• Build and maintain relationships with new and existing customers and pursue cross-selling opportunities.
• Utilize Hubspot as a CRM to manage leads, opportunities, and renewals.
• Lead client renewal discussions and identify cross-sell/upsell opportunities.
• Represent Hylant at trade events and coordinate with internal teams to meet client needs.

Skills

Sales experience

Teamwork

Communication skills

MS Office

Prospecting

Education

Bachelor's degree

Tools

Hubspot

Job description

The Opportunity: The Client Executive will develop and grow a client book of business, managing and retaining current clients and proactively identifying new business opportunities within the Chicago Benefits market.

In This Role You Will Execute On:

• Establish sales development plans to originate business with new clients.
• Build and maintain a book of business and incrementally grow the book each year.
• Actively generate sales leads through regular prospecting, cold calls, networking, account rounding, cross selling with other departments, and pursuing miscellaneous sales leads.
• Develop, maintain, and expand relationships with new and existing customers.
• Utilize Hubspot as a CRM.
• Understand requirements for new and existing customers; identify and anticipate needs and provide Hylant solutions to meet these needs.
• Schedule and conduct sales presentations with potential customers for new business.
• Manage the client renewal process; identify opportunities to cross sell and upsell based on client needs.
• Manage a book of business focusing on client strategy, growth and retention and/or co‑lead a book of business in collaboration with a Managing Partner.
• Strengthen the firm's relationships with existing clients and drive continuous improvements with an ultimate focus on business growth and retention.
• Represent Hylant at trade and industry events.
• Manage negotiations on all commission and fee arrangements in accordance with standard pricing guidelines (exceptions require management pre‑approval).
• Perform other duties and special projects as requested.

In This Role You Will Need:

• Bachelor’s degree or equivalent combination of education and work experience.
• A minimum of 4-5 years of proven insurance brokerage sales experience.
• Possess a solid foundation of Hylant sales and client service methodology.
• Hold and maintain active Life & Health License.
• Detailed working knowledge of industry resources, benchmarking information, agency management, and risk management principles.
• Intermediate Microsoft Office skills (Excel, Word, PowerPoint, and Outlook).
• Exception oral and written communication skills.
• Ability to work well in a team environment.
• Ability and willingness to travel by car or airplane for meetings, conferences, or other business‑related functions.
• Must be legally authorized to work in the United States.

Why Hylant?

Since 1935, Hylant has been a family‑owned insurance brokerage built on relationships, trust, and a people‑first mindset. We believe great work is rooted in understanding people—our clients, our communities, and each other—and delivering thoughtful solutions that rise above the expected. Anything But Typical. Everything for You. isn’t just a message; it’s how we show up. It reflects a culture where people come first, careers are supported with purpose, and going above and beyond is the standard, not the exception. At Hylant, you’re more than an employee, you’re part of a team that treats one another like family and works together to make a meaningful impact.

Why Hylant?

A Career That’s Anything But Typical. At Hylant, we don’t just offer jobs—you’re offered careers that grow with you. For over 90 years, our family‑owned business has stood for more than insurance. We stand for people. When you join Hylant, you become part of a family that champions support, respect, flexibility, and a healthy work‑life balance. It’s no surprise we’ve been named a “Best Place to Work in Insurance” for 17 consecutive years. In 2024 alone, Hylant and our incredible team earned 24 awards, celebrating our commitment to workplace culture, community involvement, and individual achievement. We’re proud to be anything but typical in our industry. Here’s what makes Hylant different: Opportunity on your terms: Whether you’re just starting out or looking to lead, we offer clear career paths, tailored development programs, and the freedom to grow in the direction that fits you best. Relationships that build people up: Our culture is rooted in empathy and collaboration. You’ll be surrounded by mentors, teammates, and leaders who care about your success. A chance to make a real impact: From serving clients with integrity to giving back to our communities, your work at Hylant will matter—locally and globally. We invest in our people through programs like the Hylant Career Academy, Leadership Catalyst, and Hylant MBA, and we celebrate the wins—big and small—along the way. If you’re looking for a place where you gain so much more.