Job Summary We are seeking a seasoned Sales Executive with a strong background in Employee Benefits to drive growth in the Chicago market. This role is ideal for a motivated professional who thrives in building new business, cultivating long-term client relationships, and leading strategic market expansion efforts. The Sales Executive will serve as an anchor hire in Chicago, shaping growth strategy, supporting recruiting efforts, and positioning the team for long-term success. Responsibilities • Develop and grow new client relationships through proactive prospecting, networking, referrals, and industry partnerships • Manage and expand a book of business, ensuring high levels of client retention and satisfaction • Analyze risk, coverage options, and program structures while providing tailored recommendations to clients • Lead strategy for middle to large group Employee Benefits accounts, delivering consultative sales solutions • Collaborate with service teams to review carrier proposals, market summaries, and renewal documents • Maintain a robust pipeline aligned with annual sales goals and agency standards • Drive cross-selling opportunities across service lines and participate in strategic market initiatives • Contribute to business growth beyond sales, including market strategy development, mentoring, and supporting potential M&A opportunities • Stay informed on industry trends, legislation, and product offerings to provide innovative solutions Required Qualifications • 6+ years of insurance sales experience with a focus on Employee Benefits • 3+ years of tenure in a single role (demonstrated stability) • Proven track record of closing business in the mid-to-large group market (100+ lives) • Current Life & Health license and active participation in the insurance industry • Strong relationship-building skills with a consultative sales approach • Ability to work independently in a market expansion environment • Excellent presentation, communication, and client advisory skills Education and Experience • Bachelors degree preferred • Prior agency-side experience strongly preferred (carrier-side considered) • Demonstrated success in leading client strategy and achieving consistent sales results Nice to Have • CEBS designation or similar advanced credentials • Experience mentoring or supporting team development • Interest in future leadership opportunities, including Sales Team Leader roles This is a high-impact opportunity with significant upside potential, including direct equity eligibility tied to performance. The right candidate will have the ability to shape the future of the Chicago market while working alongside a collaborative leadership team in a nationally ranked, growth-focused organization.