Director of Sales - Personal Lines

Overview

The Baldwin Group is an award‑winning, entrepreneur‑led insurance brokerage firm that provides commercial insurance, private insurance, employee benefits, asset protection, and risk‑mitigation services across the United States and abroad. We strive to deliver holistic and tailored solutions to our clients and foster a culture that is highly valued by the marketplace.

• Develop and execute regional sales strategies to achieve revenue and growth targets for 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 a positive customer experience.
• Manage day‑to‑day team activities, lead weekly sales huddles, and conduct monthly one‑on‑ones.
• Lead full‑cycle recruiting efforts, including sourcing, interviewing, and hiring Sales Advisors aligned with regional growth goals.
• Collaborate with training to oversee onboarding and training programs, 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 the approach.

• 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.

• Starting salary: $130,000–$150,000 per year plus bonus based on experience.
• Flexible time off policy with open PTO and up to 12 company‑observed holidays.
• Comprehensive health benefits package (medical, dental, vision).
• 401(k) with company match.
• Reimbursement for mileage and cell phone for field‑based work.
• Company card for client events, team outings, and training initiatives.
• Dedicated marketing support for lead generation and regional brand presence.
• Autonomy to build, grow, and lead a high‑performing sales team within the market.

The Baldwin Group is an equal employment opportunity firm and complies with all laws prohibiting discrimination based on race, color, religion, age, sex (including sexual orientation and gender identity), national origin or ancestry, disability, military status, marital status, or any other category protected by federal, state, or local laws. All such discrimination is unlawful, and all persons involved in the operations of the firm are prohibited from engaging in this conduct.