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Manager, Mid-Market and Group Sales; West Market) Remote

Remote / Online - Candidates ideally in
Oak Brook, DuPage County, Illinois, 60523, USA
Listing for: Inspira Financial Trust, LLC
Remote/Work from Home position
Listed on 2026-10-18
Job specializations:
  • Sales
    Area Manager
  • Management
    Area Manager
Salary/Wage Range or Industry Benchmark: 100000 - 140000 USD Yearly USD 100000.00 140000.00 YEAR
Job Description & How to Apply Below
Position: Manager, Mid-Market and Small Group Sales (West Market) Remote

Manager, Mid-Market and Small Group Sales (West Market) Remote

Work Location Type

Home Based

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.

Serving more than 7 million clients and representing over $62 billion in assets, Inspira partners with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners to help the people they support plan, save, and invest for a brighter future. Through solutions including automatic rollover services, health savings accounts, emergency savings, and custody services, Inspira is focused on delivering better outcomes for all.

Learn more at  .

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.

Our growth and culture haven't gone unnoticed -- we've been recognized on Crain's Fast 50 and Inc. 5000 for remarkable growth, and named to Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer for our workplace culture and benefits.

Don't meet every single requirement? That's okay. We know growth comes from people who are willing to learn and challenge themselves, not just check every box. If you're energized and inspired by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, we want to hear from you. We look forward to receiving your application.

Our office locations are designed to bring people together, foster collaboration, and build meaningful connections. While some roles are based at one of our office locations, remote status and role locations are subject to change, and relocation is not provided.

Job Summary & Responsibilities

The Manager, Mid-Market and Small Group Sales (West) reports to the Senior Director, Mid-Market and Small Group Sales and is the front-line leader for the West region team, which spans both Mid-Market sales executives and Small Group representatives. This is a new role at Inspira, created to put dedicated coaching and development between the Senior Director and the field. The role exists to make sellers better - through deal coaching, pipeline discipline, structured development, and fast, honest feedback - and is accountable for the West region’s new business number as the aggregate of the team’s results across both segments rather than through a personal book.

This role and its East counterpart are mirror positions, each owning both Mid-Market and Small Group coverage within their own region. The strongest performers in this seat are the bench for future senior sales leadership at Inspira.

Duties & Responsibilities:

Coaching & Seller Development

  • Coaches the West region team, across both Mid-Market and Small Group sellers, through weekly one-on-ones, deal strategy sessions, call and meeting coaching, and pipeline reviews
  • Adapts coaching approach to the seller type - Small Group representatives run higher-velocity, more transactional cycles, while Mid-Market sales executives run longer, broker-influenced, multi-stakeholder cycles
  • Helps the team build and refine outreach cadences across both segments
  • Owns onboarding, ramp, and time-to-first-sale for new sellers in both segments, in partnership with Sales Enablement
  • Drives adoption of sales plays, messaging, and AI-assisted selling tools in live selling, not just in…
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