Manager, Mid-Market and Small Group Sales (East Market) Remote
Sales & Business Development
Oak Brook, IL, USA
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