Director of Sales - Personal Lines (Hyannis)

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.Primary ResponsibilitiesDevelop and execute regional sales strategies to achieve revenue and growth targets across personal lines productsIdentify and pursue new market opportunities and distribution channels throughout the South Shore and Cape Cod areaHire, coach, and manage a team of outside Sales Advisors, ensuring strong field performance and customer experienceHandle 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 goalsWork with training to help oversee onboarding and training programs to effectively ramp new Advisors, improving time-to-productivity and early performanceBuild and maintain key client and partner relationships, driving upsell and cross-sell opportunitiesMonitor sales performance and pipeline health, providing hands-on coaching to improve productivity and close ratesEnsure compliance with all applicable insurance regulations and company policiesCollaborate with marketing, operations, and leadership to align sales strategy with broader business objectivesStay current on market trends and competitor activity to continuously refine approachKnowledge, Skills & AbilitiesProven leadership experience managing high-performing, field-based sales teamsStrong background in personal lines insurance (home, auto, umbrella, etc.)Excellent communication and coaching skillsAnalytical mindset with the ability to use data to drive decisionsAbility to operate both strategically and hands-on in a regional leadership roleProficiency in Microsoft Office, including intermediate Excel skillsEducation & Experience7–10+ years of experience in insurance salesMinimum 5 years in a leadership role, preferably managing outside/field sales teamsStrong experience in personal lines requiredExperience in the MA and New England markets strongly preferredAbility to travel within the region and attend the Kingston office several times per month after ramp-upPerks of Working at The Baldwin GroupTop 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 holidaysComprehensive health benefits package (medical, dental, vision)401(k) with company match to support long-term financial goalsMileage and cell phone reimbursement for field-based workCompany card to support client events, team outings, and training initiativesDedicated marketing support to help drive lead generation and regional brand presenceAutonomy to build, grow, and lead a high-performing sales team within your marketOngoing support and resources from a collaborative, growth-oriented organizationStarting pay is in the 130-150K range plus bonus depending on experienceAnd more….#LI-KL1IND1IMPORTANT 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.SummaryLocation: Kingston, Massachusetts, US; Hyannis, Massachusetts, US; Dennis Village, Massachusetts, US; Boston, Massachusetts, US; Nantucket, Massachusetts, USType: Full time