Health & Benefits - Sales Executive (Boston, MA)

The 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 relationships
  • Travel: 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 

Qualifications

Education & 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