Insurance Sales Trainee Program

Starkweather & Shepley is seeking motivated, driven, and entrepreneurial individuals to join our Sales Management Trainee Program. This program is designed for recent college graduates or early-career sales professionals (1–2 years of experience) who are looking to build a long‑term career in the insurance and risk management industry.

This is a structured, developmental role intended to build the next generation of insurance producers and sales leaders within our organization.

The Sales Trainee Program is a comprehensive, hands‑on learning experience that combines:

• Foundational insurance education
• Sales strategy and prospecting training
• Exposure to underwriting, claims, and service operations
• Mentorship from senior producers and leadership

Participants will gain a strong understanding of risk management solutions while developing the skills necessary to build and manage a book of business.

The insurance and risk management industry is relationship‑driven, financially rewarding, and recession‑resilient. This program offers the opportunity to build a long‑term career with unlimited earning potential while serving as a trusted advisor to businesses and individuals.

• Participate in structured training and mentorship programs
• Support senior producers in client meetings and renewal strategy discussions
• Assist in prospect research and pipeline development
• Develop new business opportunities through networking and outreach
• Learn proposal development and presentation skills
• Track activity and sales performance metrics
• Work cross‑functionally with internal teams to understand full client lifecycle