Leadership Development Program Associate Jobs in Massachusetts

At Amwins, we succeed together — and have a good time doing it.

We know people don't leave companies. They leave cultures — which is why we work so hard on ours. At Amwins, we thrive on collaboration, not cutthroat competition. Our teams work together to help each other succeed, and we do right by our clients so they can do right by theirs.

First and foremost, we invest in our employees. That investment shows in everything we do; education and development programs, comprehensive and competitive benefits, and an organizational structure that's 43% owned by employee shareholders.

Our commitment to diversity, equity and inclusion helps cultivate an open, welcoming workplace that reflects the communities we serve. ​You will have the opportunity volunteer within Amwins through a wide range of committees and in your community through the Amwins Foundation and Summer of Service.

Working at Amwins means you love what you do, how you do it and, ultimately, who you do it with. Whether it's today or 150 years from now, we continue to invest in our culture and your development so opportunities for growth and career advancement are never in short supply.

At Amwins, we win together — and have a good time doing it.

Learn more about us at amwins.com.

We see you in Amwins blue!

Launch your Sales and Underwriting Career with Amwins

At Amwins, we're not just developing underwriters — we're building elite sales professionals.

Our Underwriter Development Program (UDP) at Amwins Access is a 2.5-year intensive training track designed to fast-track your career as a Production Underwriter — a role that combines strategic sales with technical underwriting.

This role is not a traditional underwriting position — it is a highly sales-driven role where you will be measured on performance metrics, build and manage your own profitable book of business, and take ownership of sourcing and developing new opportunities to underwrite throughout the program.

If you're entrepreneurial, thrive in a competitive environment, and want a career where your effort drives your income, this is your runway.

Please note that this position will have two start dates: April & June 2027

Program Break Down

Phase 1: Underwriting, Technical & Sales Skills Training

• Participate in cohort-based, instructor-led training sessions and case studies
• Learn core underwriting concepts, risk evaluation, pricing, and policy structure
• Apply training directly in the office through hands-on underwriting experience alongside a dedicated mentor
• Quote new business and renewal accounts from retail agents
• Assist with servicing existing accounts, including endorsements, renewals, and policy changes
• Prospect for new retail agency relationships and business opportunities
• Conduct cold calls and attend agency visits
• Build and maintain relationships with retail agents and carrier partners
• Gain experience presenting products, negotiating terms, and positioning solutions
• Continue developing underwriting judgment while expanding external-facing responsibilities

Phase 2: Business Development, Provisional Year

• Begin building and managing an individual book of business
• Develop and retain a client base while driving new revenue
• Strengthen long-term agency and carrier relationships
• Manage the end-to-end lifecycle of accounts with increasing autonomy
• Graduate from the program upon achieving established revenue targets

Phase 3: Post Graduation of Program (Production Underwriter)

• Continue to grow and manage a personal book of business at Amwins
• Prospect for new business by developing strong relationships with retail agents through both traditional and creative marketing strategies
• Stay current on insurance company offerings and effectively leverage market opportunities to drive production
• Identify and develop new business markets and/or lines of business using sales techniques rooted in trust and long‑term relationship building
• Mentor, train, and develop new team members to support sustained growth and performance

Key Responsibilities:

• Drive new revenue through relationship-based sales with retail agents.
• Get real-world training in sales strategy, negotiation, and market development.
• Analyze risk and underwrite accounts across Commercial Lines
• Leverage exclusive carrier relationships and state-of-the-art technology
• Travel to industry events, build your network, and learn from the best in the business.
• Mentor and manage your own team after completing the program

What We're Looking For:

• Recent graduates (Bachelor's preferred) with fewer than 3 years of work experience
• Less than 12 months of insurance experience
• Competitive, goal-oriented individuals with a desire to excel in sales
• Strong communicators who love solving problems and building relationships

What You'll Get:

• Structured development path with clear milestones
• Dedicated mentorship and leadership support
• Opportunity to build a long-term career at Amwins upon program graduation
• Base salary with unlimited income opportunity upon program graduation
• Full benefits from day 1
• Access to exclusive insurance markets and powerful tech to help you win

At Amwins, we win together — and have a good time doing it.