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….
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IMPORTANT NOTICE:
This position description is intended to describe the level of work required of the person performing in the role and is not a contract. The essential responsibilities are outlined; other duties may be assigned as needs arise or as required to support the organization. All requirements may be subject to reasonable accommodation to applicants and colleagues who need them for medical or religious reasons.
Click here for some insight into our culture!
The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.
Skills Required
- 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
The Baldwin Group Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about The Baldwin Group and has not been reviewed or approved by The Baldwin Group.
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Healthcare Strength — Health coverage includes flexible medical options, 24/7 telemedicine, mental health support, company‑paid life and disability, plus dental and vision. Feedback suggests these comprehensive offerings contribute meaningfully to total rewards.
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Leave & Time Off Breadth — Time‑off programs span parental leave, paid holidays, paid sick days, and flexible PTO, with some teams citing unlimited PTO. Feedback suggests flexible PTO depth is a valued element of the package.
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Equity Value & Accessibility — Equity grants are provided to all new hires. Feedback suggests broad‑based equity can enhance perceived fairness and long‑term value.
The Baldwin Group Insights
What We Do
BRP is now The Baldwin Group! We’ve updated our name to reflect our unified group of talented teams across the country. The Baldwin Group is a cohesive group of experts in business insurance, employee benefits, retirement planning, and all areas of private and personal insurance. Since our founding in 2011, we’ve evolved from a local business into a national firm with a vast network of specializations and industry practices for the benefit of our more than two million clients across the country. In addition, we have built excellent relationships with a wide range of insurance company partners. These relationships, coupled with our entrepreneurial and family-oriented culture, and deep expertise enable us to seamlessly deliver a breadth of innovative solutions to clients. At The Baldwin Group, we help provide the solutions our clients need to have confidence and gain peace of mind as they pursue what’s possible for themselves, their families, and their businesses. Whether they are renting their first apartment or buying a larger home, opening a small business or taking their company public, we offer solutions to support them on every step of their journey. This has been our story since the beginning—we provide the indispensable expertise and quality insights that give our clients peace of mind to pursue their purpose, passion, and dreams. And that’s what The Baldwin Group will continue to do for years to come: we Protect the Possible℠.
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