Enterprise Sales Executive ( Remote West Coast (California, Oregon, Washington,
Inspira Financial, Oak Brook, IL, United States
Join Us!
Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people‑centric and client‑obsessed in every interaction; a community of forward‑thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey – relentlessly pursuing better outcomes for all. We believe in finding the best talent!
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? Here at Inspira Financial, we believe there is no “perfect” candidate and encourage applying even if all the requirements listed aren’t met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! Check out this Inspira Financial video to learn more about our company. 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. Job Summary & Responsibilities
The Enterprise Sales Executive reports to the Managing Director, Head of Sales in the Health & Benefits Sales Department. This pivotal role drives business growth and strengthens 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. 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: 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. Other Requirements
Frequent travel, 50% (regional and national travel required). Additional requirements:
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.
Pay Range
$125,000–$145,000 per year. Compensation & Benefits
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.
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Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people‑centric and client‑obsessed in every interaction; a community of forward‑thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey – relentlessly pursuing better outcomes for all. We believe in finding the best talent!
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? Here at Inspira Financial, we believe there is no “perfect” candidate and encourage applying even if all the requirements listed aren’t met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! Check out this Inspira Financial video to learn more about our company. 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. Job Summary & Responsibilities
The Enterprise Sales Executive reports to the Managing Director, Head of Sales in the Health & Benefits Sales Department. This pivotal role drives business growth and strengthens 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. 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: 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. Other Requirements
Frequent travel, 50% (regional and national travel required). Additional requirements:
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.
Pay Range
$125,000–$145,000 per year. Compensation & Benefits
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.
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