[Hiring] Manager, Mid-Market and Small Group Sales @Inspira Financial

Role Description

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.

Qualifications

• Education & Experience:
  • Minimum required:
    • 7+ years of sales experience in employee benefits, health and benefits, consumer directed health, or a closely related field.
    • 2+ years leading, managing, or formally coaching a team of sellers.
    • Demonstrated experience coaching sellers across both a consultative, broker-influenced motion and a higher-velocity, transactional motion.
    • Consistent record of quota attainment as an individual contributor prior to moving into leadership.
    • Bachelor’s degree in Business, Marketing, or a related field, or an equivalent combination of education, experience, and training, required.
  • Additional preferred:
    • Experience with consumer directed health products (HSA/FSA/HRA/COBRA) preferred.
    • Experience selling or leading in a broker- and consultant-influenced market preferred.
    • Experience leading a team through a coverage model or operating model change preferred.
• Skills & Abilities:
  • A developer of people who can point to specific sellers coached to measurably better performance.
  • Strong deal coaching and consultative selling skills across both transactional (Small Group) and multi-stakeholder, broker-influenced (Mid-Market) sales cycles.
  • Holds direct performance conversations early, and does it in a way that keeps the relationship intact.
  • Reads a pipeline and identifies the behavior driving the result, not just the result.
  • Fluency with Salesforce and AI-powered productivity tools.

Requirements

• Typical schedule is Monday-Friday, with flexibility to work evenings or weekends as needed to support client, partner, and industry engagements.
• Travel in up to 50% of weeks, typically one to two days at a time, for seller field time, client and broker meetings, and industry events.
• Must reside in the Pacific or Mountain time zone, within the assigned region.
• Ability to provide personal transportation from time to time.
• Prolonged periods of sitting and operating standard office equipment; occasionally lifts up to 25 pounds.