Regional Sales Director - New York City/Metro Territory

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

The Regional Sales Leader plays a critical role in advancing Trustmark’s growth vision by leading, developing, and challenging Regional Sales Directors and/or Regional Sales Representatives, while also personally producing within an assigned territory. This role is responsible for executing the annual sales plan in alignment with Trustmark’s broader business strategy and for helping shape a high‑performing, consultative sales organization built for long‑term success.

Trustmark is intentionally evolving—expanding its product portfolio, strengthening its distribution capabilities, and investing in the people, processes, and partnerships that will fuel sustainable growth. As a result, this role goes beyond managing results; it is about building leaders, elevating performance standards, and creating the conditions for consistent excellence across the region.

This position is designed for a hands‑on, growth‑minded leader who leads by example, believes in coaching and accountability, and takes pride in helping others become the best version of themselves. Success in this role comes from the ability to inspire trust, teach consultative selling skills, challenge assumptions, and create a culture where high expectations are matched with strong support and development.

Trustmark’s Growth Vision & Culture

At Trustmark, growth is intentional and people‑driven. The organization is focused on building a sales culture where leaders develop talent, collaboration is expected, and accountability is embraced. Sales leaders are empowered to influence strategy, bring forward market insights, and help shape how Trustmark competes and wins in the marketplace.

Trustmark values:

• Leadership that develops people, not just pipelines
• High standards paired with coaching and support
• Consultative selling rooted in trust and long‑term relationships
• Collaboration across teams to deliver better outcomes
• Continuous improvement as the business evolves

This role is ideal for a leader who wants more than a title—someone who wants to leave a mark on the organization, build strong teams, and grow alongside a company that is investing in its future.

Increases new business sales through establishing strong, consultative partnerships with major worksite and voluntary benefit distributors to include brokers, agents, financial planners, consultants, and employees within Trustmark. Customers typically include hospitals, medical centers, manufacturing, public entities, services, warehousing, and wholesale trade who want to offer their stable workforce a comprehensive benefit solution. Activities will include learning and staying informed on health care trends, market intelligence and product information for all product solutions within voluntary benefits; establishing, updating and managing target account lists and pipeline management; following a comprehensive sales process that will include marketing programs, educational seminars, customer needs analysis meetings, presentations to develop new and expand existing accounts; managing both external and internal stakeholders throughout the sales process and contributing to sales planning, forecasting and product development.

Key Accountabilities

• Achieve annual new business sales, net growth & reenrollment objectives as assigned:

• Demonstrate the value proposition to distribution partners.

• Direct and manage the acquisition process by establishing priorities with sales support team and serving as a liaison between producers and customers to maximize sales efforts.

• Proactively develop and maintain an effective relationship with Sales Implementation, Key Account Managers, Case Underwriting & Marketing. 

• Prospecting:

• Generate new business opportunities by leveraging existing relationships, prospecting new relationships, conducting market analysis and cold calling channel distributors.

• Partner with marketing and product development in developing programs to educate the network channel on Trustmark value proposition to create demand in the marketplace.

• Partner with distribution channel to identify new sales opportunities, influence the RFP design, and develop solutions that will secure new business.

• Reporting & Analytics

• Monitor and report on competition to evaluate Trustmark’s position in the marketplace.

• Actively utilize Salesforce.com for activity reporting, forecasting, business requests, workflow management, travel bookings and expense reporting.

• Provide monthly reports of pipeline, forecasts and metrics using Salesforce automation tool.

• Other duties as needed/assigned.

Minimum Requirements

• 5 years of Voluntary product sales or equivalent work experience

• Consultative sales experience required. 

• Experience generating and analyzing reports to enhance sales or customer experience.

• Excellent oral & written communication skills; persistent and patient in endeavoring to fully understand customer/producer needs and offer valuable information and solutions.

• Ability to work independently, make good decisions consistent with divisional objectives and in a timely manner, and handle conflict with minimal oversight.

• Exceptional organizational skills, adept at handling multiple tasks simultaneously, committed to follow through and completing assignments in a timely & professional manner.

• Interpersonal effectiveness with proven ability to establish/maintain mutually respectful relationships with managers, peers, support staff, agents/brokers and customers; handle conflict, resolve complex issues, negotiate, achieve consensus and promote team spirit.

• Capable of operating the complete MS Office Suite

The compensation range for this role is (based on the corporate location in Lake Forest, Illinois):

$92,359.68 - $133,409.90 per year

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 bonus. 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

In addition to compensation, we offer a comprehensive benefits package that includes: 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.  For questions about compensation and benefits, please speak to the Recruiter if you decide to apply and are selected for an interview.

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.