Enterprise Sales Executive ( Remote West Coast (California, Oregon, Washington, Nevada and Arizona)

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 Enterprise Sales Executive will report to the Managing Director, Head of Sales in the Health & Benefits Sales Department. This role a pivotal role in driving business growth and strengthening our position in the Health & Benefits space. At Inspira we have launched our next generation platform, that brings a modern, modular and configurable solution, to an industry dominated by players with antiquated legacy platforms. Inspira is poised to disrupt the market and transform how companies support the health and well-being of their workforce. This role will have the opportunity to work with high-profile enterprise accounts, negotiate complex deals, and build lasting relationships with brokers, partners, and key stakeholders. This is a unique chance to shape the future of health and benefits solutions while advancing your career within a dynamic and rapidly growing company.
Key Responsibilities:

• Drive New Business Growth:Identify, engage, and develop relationships with key target organizations in your assigned territory to sell Inspira's Health & Benefits services.
• Build Strong Relationships:Cultivate productive, long-term relationships with brokers, consultants, partners, and key decision-makers to generate a consistent pipeline of high-value opportunities.
• Consultative Selling:Leverage your expertise to understand complex, multi-faceted client needs and match them with Inspira's innovative solutions, delivering value at every step of the sales process.
• Lead Complex Negotiations:Manage and negotiate multi-stakeholder deals, ensuring both client needs and organizational objectives are met while maintaining profitability.
• Pipeline Management:Maintain a healthy, well-managed sales pipeline through effective prospecting, relationship-building, and follow-through. Ensure all opportunities are tracked and reported accurately within Salesforce CRM.
• Sales Strategy Execution:Develop and implement tailored strategies for driving sales success, ensuring objectives are met and exceeded within your assigned territory.
• Industry Leadership:Represent Inspira at industry events, conferences, and networking opportunities to build awareness, create new business opportunities, and stay on top of market trends.
• Cross-Functional Collaboration:Collaborate closely with internal teams, including marketing, customer success, and operations-to deliver seamless, client-centric solutions that drive customer satisfaction and long-term loyalty.

• Other duties as assigned.

People Leader Responsibilities:

• High-performing individual contributor, without direct or indirect reports.

Preferred Qualifications
Education & Experience:
Minimum required:

• 15+ years of B2B sales experience in complex enterprise environments, within the group benefits, consulting, or financial services industries
• Bachelor's degree in business, marketing, healthcare or equivalent combination of education, experience and training required

Skills & Abilities:

• Consultative Selling Skills:Strong ability to understand clients' needs, identify key decision-makers, and develop tailored solutions that drive business value.
• Track Record of Success:A demonstrated history of consistently meeting or exceeding sales quotas and driving high-value deals to closure, in B2B direct selling environments.
• Relationship Building:Proven experience cultivating relationships with brokers, partners, and senior executives. Able to mobilize internal resources and leverage existing networks to maximize sales potential.
• Excellent Communication Skills:Strong verbal and written communication skills, with the ability to present complex information in a compelling and accessible manner.
• Strategic and Analytical Thinking:The ability to develop and execute strategic sales plans, with an analytical approach to evaluating market trends, competition, and opportunities.
• Self-Motivated and Results-Oriented:Driven to succeed and eager to learn and adapt quickly in a fast-paced environment.
• Experience with Salesforce CRM:Familiarity with Salesforce or other CRM platforms to track and manage sales opportunities.

Other Requirements:

• Frequent travel, 50% (regional and national travel required)
  • Ability to provide personal transportation for training or meetings may be required
• Occasionally lifts up to 25 pounds
• Prolonged periods of sitting and operating standard office equipment

Compensation & Benefits
$125,000-$145,000 per year OTE 290k +