Field Sales Executive - Chicago, IL

Trustmark Job Opportunity

Trustmark's mission is to improve wellbeing for everyone. It is a mission grounded in a belief in equality and born from our caring culture. It is a culture we can only realize by building trust. Trust established by ensuring associates feel respected, valued and heard. At Trustmark, you'll work collaboratively to transform lives and help people, communities and businesses thrive. Flourish in a culture of diversity and inclusion where appreciation, mutual respect and trust are constants, not just for our customers but for ourselves. At Trustmark, we have a commitment to welcoming people, no matter their background, identity or experience, to a workplace where they feel safe being their whole, authentic selves. A workplace made up of diverse, empowered individuals that allows ideas to thrive and enables us to bring the best to our colleagues, clients and communities.

About the Role

Responsible for driving new business growth and strengthening broker relationships within the small business segment (typically 5 - 100 employees) in a designated territory. Has high visibility and consistent presence in the market to build and grow broker relationships and drive sales. Combines market expertise, consultative selling, and strong field presence to position our medical insurance solutions as the preferred choice for brokers and their employer clients.

Key Accountabilities:

• Develop and grow broker relationships through regular field visits, joint selling, and ongoing engagement to increase quoting activity and new business submissions. Deliver compelling product presentations to brokers, employers, and industry partners, clearly articulating value, differentiation, and cost containment strategies. Represent the company at industry events, broker meetings, and local market activities to strengthen brand presence and generate new opportunities.
• Maintain deep market expertise, including competitor positioning, pricing trends, and regulatory changes impacting the small?group segment.
• Prospect and close new small?business medical groups, leveraging product knowledge, competitive insights, and a consultative sales approach.
• Track and report pipeline activity in CRM; analyze sales performance, and market insights to inform strategy and forecasting.
• Partner with underwriting, client management, and marketing to ensure a seamless experience from quote to implementation.

Minimum Requirements:

• Bachelor's Degree with 4 - 6 years relevant sales experience OR High School Diploma/GED with 6 - 8 years relevant sales experience.
• Active health and life license within 90 days of hire.

Sales Record & Approach

• Demonstrated record of sales success in small group or level-funded health plans.
• Excellent negotiation skills.
• Strategic and consultative sales approach with proven ability to build and maintain trusted broker relationships.
• Ability to travel up to 50% of the time, primarily but not exclusively local.

Other Skills:

• Communication: excellent interpersonal and presentation skills, including the ability to comfortably and confidently deliver information to large groups.
• Time Management: Ability to prioritize and manage time efficiently to ensure all key job accountabilities are completed.

Preferred:

• Dynamics CRM experience.

The base salary range for this role is $80,000 - $100,000 with an additional Sales Incentive Compensation package. The final salary offer will be determined based on factors such as location, qualifications, experience, skill set, and other relevant factors. This position may also be eligible for commission. We understand that compensation is an important factor when considering a new opportunity, and we strive to provide a competitive salary within the market.

Brand: Trustmark

Trustmark benefits include health/dental/vision, life insurance, FSA and HSA, 401(k) plan, Employee Assistant Program, Back-up Care for Children, Adults and Elders and many health and wellness initiatives. We also offer a Wellness program that enables employees to participate in health initiatives to reduce their insurance premiums.

Trustmark is committed to leveraging the talent of a diverse workforce to create great opportunities for our people and our business. We are an equal opportunity employer, including disability and protected veteran status.