Manager Mid-Market and Small Group Sales West Market Remote

Millennium Trust Company, LLC

  • Oak Brook, IL
  • 7 days ago
  • Remote

    Highlights

    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. 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.

    Numbers & Facts

    LocationOak Brook, IL (
    Remote
    )

    Description

    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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