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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
Full Time, Remote/Work from Home position
Listed on 2026-11-01
Job specializations:
  • Sales
    Area Manager
  • Management
    Area Manager
Salary/Wage Range or Industry Benchmark: 120000 - 180000 USD Yearly USD 120000.00 180000.00 YEAR
Job Description & How to Apply Below
Position: Manager, Mid-Market and Small Group Sales (West Market) Remote

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 training
Revenue & Pipeline Execution
  • Owns the West region’s combined Mid-Market and Small Group new business target as the aggregate of team quotas, and delivers accurate weekly and monthly forecasts for both segments
  • Inspects and progresses deals, and attends key prospect, broker, and finalist meetings in a coaching capacity rather than as the primary seller
  • Sets and holds regional activity standards, prospecting expectations, and CRM hygiene across Inspira’s Salesforce environments
  • Escalates deal-level risk and resourcing needs early rather than at close
Market & Cross-Functional Partnership
  • Supports regional broker and consultant relationships in coordination with the Head of Broker & Consulting Relations
  • Attends local and national events alongside sellers on the team to grow Inspira’s footprint in the market
  • Provides field intelligence on competitive activity, pricing pressure, and product gaps across both Mid-Market and Small Group
  • Contributes to the rollout of the Small Group inside-sales motion in the region
  • Other duties as assigned.
People Leader Responsibilities:
  • Manages a combined West region team of Mid-Market sales executives and Small Group representatives; team size varies with coverage and segment mix (typically 10-12 direct reports)
  • Is hands-on and credible as a coach; sellers should be able to point to specific things they do better because of this leader
  • Provides timely, specific feedback and builds development plans grounded in observed selling behavior, not results alone
  • Addresses underperformance early and directly, in partnership with the Senior Director and HR
  • Participates in recruiting, interviewing, hiring, and onboarding for the region across both segments
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