Health & Benefits - Sales Executive (Boston, MA)

Join Us!
Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.
Our values shape how we show up every day. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.
Join us on our journey as we work together to take on the complex and the everyday--turning collective effort into life-changing impact that enriches lives and helps build a better future. Learn more at inspirafinancial.com.
We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday). This requirement does not apply to support specialist positions.
Don't meet every single requirement? That's okay. At Inspira Financial, we know growth comes from people who are willing to learn, challenge themselves, and aim higher. We value individuals who lead with heart, cultivate trust, and collaborate to win together. If you're energized by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, Inspira Financial could be the right next step in your journey. We look forward to receiving your application.
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
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 strategy focused on driving net new business and expanding partner relationships

• 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

Preferred Qualifications
Education & Experience:

• 4-7 years of experience i n 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

Compensation & Benefits
$87,000-$107,000 per year, OTE $214K+