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

IF
Inspira Financial

Sales & Business Development

Oak Brook, IL, USA

Posted on Oct 15, 2026

The Manager, Mid-Market and Small Group Sales (East) reports to the Senior Director, Mid-Market and Small Group Sales and is the front-line leader for the East 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 East 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 West 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 East 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 East 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 East 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