Director, Sales Enablement

🏢 Trustmark Services Company · all 3 jobs
📍 United States
💰 USD 92,359.68 - 133,409.9 / annual
📅 Posted Sep 9, 2026 · via Himalayas
🏷 Sales Enablement, Sales Operations, Sales Management, Learning And Development, Health Insurance Sales, Sales Enablement Director +3 more
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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 equipping the sales organization with the training, tools, insights, and processes needed to drive growth in the level-funded health insurance market. Partners closely with Sales, Client Management, Product, Marketing, Underwriting, and Operations to improve sales effectiveness, execute on strategy, streamline workflows, and ensure the field is prepared to sell and retain business. Key Accountabilities:

- Analyze sales performance data and provide reporting to identify trends and opportunities across regions, states, sales consultants, segments, products, and CRM platform. Provide actionable insights as a result of data analysis.

- Lead or support strategic projects that improve sales productivity, persistency, and customer relationships, broker engagement, or market competitiveness.

- Assist with developing and maintaining onboarding and training programs for new and existing sales and client management associates.

- Help coordinate and plan market events, annual Sales Summit, leadership meetings, and broker/MGA councils.

- Support change management efforts for new systems, processes, or go to market strategies.

Minimum Requirements:

- 8+ years of experience in sales enablement, sales operations, project management, training, or related roles within health insurance or employee benefits.

- Experience in a carrier, TPA, or benefits consulting environment.

- Background in project management or process improvement including data analysis.

- Experience working with brokers, employer groups, or carrier sales teams.

- Excellent communication, facilitation, and presentation skills.

- Proficiency with CRM systems, learning management systems, and data visualization tools.

- Strategic thinking with strong execution discipline.

- Data driven decision making.

- Cross functional collaboration.

- Strong organizational and project management skills.

- Ability to influence without authority.

Preferred:
- Bachelor’s Degree

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 opportu

Flights + hotels

This role requires you to be in the United States. If that means relocating or flying in, it is worth checking fares before you commit to a start date.

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