The Director of Sales will lead the strategy and execution of personal lines insurance sales across the Northeast region. The position will report out of the Kingston, MA office, with remote hybrid availability based on candidates location. This role is responsible for driving revenue growth, managing a team of outside Sales Advisors, and expanding market presence within the region.

The position will report out of the Kingston, MA office, with remote hybrid availability based on candidates location.

Primary Responsibilities

• 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

Knowledge, Skills & Abilities

• Proven leadership experience managing high-performing, field-based sales teams
• Strong background in personal lines insurance (home, auto, umbrella, etc.)
• Excellent communication and coaching skills
• Analytical mindset with the ability to use data to drive decisions
• Ability to operate both strategically and hands-on in a regional leadership role
• Proficiency in Microsoft Office, including intermediate Excel skills

Education & Experience

• 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

Perks of Working at The Baldwin Group

• Top 15 publicly traded insurance broker in the United States with an amazing culture.
• 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
• Starting pay is in the 130-150K range plus bonus depending on experience
• And more….

#LI-KL1

IND1