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

Job Summary & Responsibilities

The Enterprise Sales Executive will report to the Managing Director, Head of Sales in the Health & Benefits Sales Department. This role is pivotal in driving business growth and strengthening our position in the Health & Benefits space. You will work with high‑profile enterprise accounts, negotiate complex deals, and build lasting relationships with brokers, partners, and key stakeholders. This unique opportunity lets you shape the future of health and benefits solutions while advancing your career within a dynamic, rapidly growing company.

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.

Remote status and role locations are subject to change. 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. Relocation is not provided.

• 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‑faced 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.

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

• 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.

• Strong consultative selling skills: ability to understand clients' needs, identify key decision makers, and develop tailored solutions that drive business value.
• Track record of success: 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: 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.

• 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.

$125,000‑$145,000 per year OTE 290k +.

The compensation for this position will vary depending on factors such as your location, skills and experience. The compensation package may also include incentive and bonus opportunities. Inspira provides industry‑leading benefits including, but not limited to: healthcare, 401(k) savings plan, company holidays, paid time off, parental leave and an employee assistance program.