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

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

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

Other 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 East 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