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

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 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+