Director of Sales – Personal Lines

The Baldwin Group

Director of Sales leading personal lines insurance sales strategy across the Northeast. Driving revenue growth and managing a team of Sales Advisors at The Baldwin Group.

Posted 5/15/2026full-timeKingston • Massachusetts • 🇺🇸 United StatesLead💰 $130,000 - $150,000 per yearWebsite

About the role

Key responsibilities & impact

Develop and execute regional sales strategies to achieve revenue and growth targets across personal lines products
Identify and pursue new market opportunities and distribution channels throughout the South Shore and Cape Cod area
Hire, coach, and manage a team of outside Sales Advisors, ensuring strong field performance and customer experience
Handle day to day activities of team, lead weekly sales huddles and monthly one on ones
Lead full-cycle recruiting efforts, including sourcing, interviewing, and hiring high-quality Sales Advisors aligned to regional growth goals
Work with training to help oversee onboarding and training programs to effectively ramp new Advisors, improving time-to-productivity and early performance
Build and maintain key client and partner relationships, driving upsell and cross-sell opportunities
Monitor sales performance and pipeline health, providing hands-on coaching to improve productivity and close rates
Ensure compliance with all applicable insurance regulations and company policies
Collaborate with marketing, operations, and leadership to align sales strategy with broader business objectives
Stay current on market trends and competitor activity to continuously refine approach

Requirements

What you’ll need

7–10+ years of experience in insurance sales
Minimum 5 years in a leadership role, preferably managing outside/field sales teams
Strong experience in personal lines required
Experience in the MA and New England markets strongly preferred
Ability to travel within the region and attend the Kingston office several times per month after ramp-up

Benefits

Comp & perks

Flexible time off policy, including an open PTO structure and up to 12 company-observed holidays
Comprehensive health benefits package (medical, dental, vision)
401(k) with company match to support long-term financial goals
Mileage and cell phone reimbursement for field-based work
Company card to support client events, team outings, and training initiatives
Dedicated marketing support to help drive lead generation and regional brand presence
Autonomy to build, grow, and lead a high-performing sales team within your market
Ongoing support and resources from a collaborative, growth-oriented organization

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Hard Skills & Tools

insurance salessales strategy developmentrecruitingcoachingperformance monitoringpipeline managementupsellingcross-sellingonboardingtraining program oversight

Soft Skills

leadershipteam managementcommunicationrelationship buildingcoachingstrategic thinkingproblem-solvingadaptabilitycollaborationcustomer experience focus