Director of Sales - Personal Lines

The Baldwin Group • Boston, MA

1d • Hybrid

About The Position

The Baldwin Group is an award-winning entrepreneur-led and inspired insurance brokerage firm delivering expertly crafted Commercial Insurance and Risk Management, Private Insurance and Risk Management, Employee Benefits and Benefit Administration, Asset and Income Protection, and Risk Mitigation strategies to clients wherever their passions and businesses take them throughout the U.S. and abroad. The Baldwin Group has award-winning industry expertise, colleagues, competencies, insurers, and most importantly, a highly differentiated culture that our clients consider an invaluable expansion of their business. The Baldwin Group (NASDAQ: BWIN), takes a holistic and tailored approach to insurance and risk management. 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.

Requirements

• 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
• 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

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

Benefits

• Flexible time off policy, including an open PTO structure
• up to 12 company-observed holidays
• Comprehensive health benefits package (medical, dental, vision)
• 401(k) with company match
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed