Health & Benefits - Sales Executive (Boston, MA)

Job DescriptionThe Sales Executive reports directly to the Head of Field Sales within the H&B Sales department and is responsible for driving business growth across the small market territory segment (1–249 benefit-eligible employees). This role focuses on developing and nurturing strategic relationships with Aetna and Meritain Health Field Sales and Service Organizations, managing channel partnerships, and converting inbound leads through a consultative sales approach. The Sales Executive will oversee all business development efforts within their territory, including marketing, communications, training, and competitive analysis, while maintaining a strong in-market presence with regular travel to key markets. Duties & Responsibilities: Own and execute a defined territory (Boston and New England) strategy focused on driving net new business and expanding partner relationshipsTravel: Typically, 2 overnight trips every other week, averaging 4-5 nights per month during peak months (about 8 months per year)Proactively build and manage a pipeline through outbound prospecting, partner referrals, and inbound lead conversion Establish and grow relationships with key partners including Aetna, Meritain Health, brokers, payroll providers, and other centers of influence Develop and execute a structured market engagement plan including call cadence, email outreach, and field activity Represent Inspira in both virtual and in-person meetings, broker events, and industry conferences to drive awareness and demand Consistently identify opportunities to increase visibility, strengthen partnerships, and improve win rates within assigned territory Lead the full sales cycle from initial outreach through close, including discovery, positioning, proposal development, and negotiation Effectively communicate the value of Inspira’s solutions (HSA, FSA, COBRA, and related offerings) in a clear and consultative manner Drive urgency in the sales process by aligning timelines, managing stakeholders, and overcoming objections Partner cross-functionally with internal teams (implementation, client success, sales operations) to ensure a smooth transition from sale to onboarding Identify and drive cross-sell opportunities across product lines by leveraging existing relationships and client needs Maintain accurate and up-to-date pipeline activity in Salesforce, including forecasting, reporting, and opportunity management Leverage data and performance metrics to continuously refine outreach strategy and improve conversion rates Travel as needed for client meetings, partner engagement, and national or regional events Take ownership of individual performance against quota and activity targets, demonstrating accountability and a results-driven mindset Contribute to a high-performance team culture through collaboration, knowledge sharing, and continuous improvement Perform other duties as assigned Job RequirementsEducation & Experience: 4-7 years of experience in field sales and account management Bachelor's Degree or equivalent Skills & Abilities: 4+ years of B2B sales experience required (preferably in SMB, benefits, payroll, or adjacent industries) Proven track record of consistently meeting or exceeding quota in a metrics-driven environment Experience with outbound prospecting and pipeline generation (calls, email, partner outreach) Ability to build and manage relationships with brokers, payroll partners, and centers of influence Strong consultative selling skills with the ability to uncover needs and position value-based solutions Experience in health & benefits, financial services, or HR-related industries preferred Highly organized with strong time management and the ability to manage multiple deals simultaneously Analytical mindset with the ability to interpret data, identify trends, and adjust strategy accordingly Strong attention to detail with a focus on accuracy and follow-through Ability to operate with urgency and meet deadlines in a fast-paced environment Excellent verbal and written communication skills Strong presentation and storytelling ability across multiple audiences (clients, brokers, partners) Ability to simplify complex products and explain them clearly and confidently Demonstrated ability to learn new products, systems, and industry concepts quickly Comfortable operating in a growing and evolving environment with changing priorities Proficiency in Microsoft Excel, Word, and Outlook Experience with Salesforce CRM or similar CRM required Strong collaboration skills with the ability to work cross-functionally (sales, implementation, service) High level of accountability, coachability, and competitiveness Other Requirements: Frequent travel 20% Ability to provide personal transportation from time to time Prolonged periods of sitting at a desk and working on a computer Job DetailsJob Type: Full-timeCategory: SalesSalaried: Salaried