Remote Director of Sales Enablement & Strategy

Trustmark; Boston (MA); Remote; USD 92,000 - 133,000; Full time

Benefits offered by this job

Health/dental/vision

Life Insurance

FSA/HSA

401(k) plan

Employee Assistance Program

Wellness program

Job summary

Trustmark is seeking a senior sales enablement professional to equip the sales organization with training, tools, insights, and processes to drive growth in the level-funded health insurance market. You will partner with Sales, Client Management, Product, Marketing, Underwriting, and Operations to improve sales effectiveness and streamline workflows.

The role emphasizes data analysis, onboarding programs, and coordinating market events to support broker engagement and market competitiveness.

Qualifications

• 8+ years of experience in sales enablement, sales operations, project management, training, or related roles in 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.

Responsibilities

• 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.

Skills

Sales enablement

Sales operations

Project management

Data analysis

Communication skills

B2B health insurance knowledge

Education

Bachelor’s Degree

Tools

CRM systems

Learning management systems

Data visualization tools

Job description

Trustmark is seeking a senior sales enablement professional to equip the sales organization with training, tools, insights, and processes to drive growth in the level-funded health insurance market. You will partner with Sales, Client Management, Product, Marketing, Underwriting, and Operations to improve sales effectiveness and streamline workflows.

The role emphasizes data analysis, onboarding programs, and coordinating market events to support broker engagement and market competitiveness.