Sr. Director, Head of Field Sales Mid Market - West Coast (Remote)

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!
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 want to 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! We look forward to receiving your application! 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. 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 Sr. Director, Head of Field Sales, will report to the Managing Director, Head of Health & Benefits Sales in the H&B Sales department. This role will oversee the National Sales team of Senior Sales Executives working with industry brokers, consultants, advisors, and direct to plan sponsors. This role will establish business strategies, execute operational plans and drive new revenue growth through this important source of business. This role will drive the national broker/consultant development strategy with a focus on the top 10 firms. This role will direct Sales Operations, Marketing and Strategy as strategic resources. This role will include participation on the PayFlex National Producer Advisory Board and as a member of the Sales Leadership team. This role will collaborate with the Senior Directors for both the Aetna Enterprise and Channel Partnerships.
Duties & Responsibilities:

• Set, communicate and execute operational strategy and performance measures in line with company, segment, region and market goals
• Ensure achievement of sales, membership growth, retention and profitability goals
• Manage team of senior sales executives
• Manage and track business development efforts nationally and by market
• Contribute as a member of the sales leadership team
• Recruit, train and develop sales executives
• Other duties as assigned

Supervisory Responsibilities:

• 5-8 direct reports
• Recruits, interviews, hires, and trains new staff.
• Oversees the daily workflow of the department.
• Provides constructive and timely performance evaluations.

Preferred Qualifications
Education & Experience:

• 15+ years of experience in field sales, account management
• Bachelor's Degree in business, communications, or related

Skills & Abilities:

• Excellent analytical skills with a proactive nature
• Strong organization skills with a drive to meet deadlines
• An affinity for accuracy and efficiency
• Proficiency in Microsoft Excel, Word (including mail merge) and Outlook
• Strong verbal and written communication skills
• An aptitude for prioritization and multi-tasking
• Strong collaboration skills
• A drive to learn and apply new concepts quickly
• Experience with Salesforce CRM preferred

Other Requirements:

• Frequent travel (50%)
  • Ability to provide personal transportation from time to time
• Prolonged periods of sitting at a desk and working on a computer

Compensation & Benefits
$170,000-$180,000 per year base OTE $300k+