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

Inspira Financial•Oak Brook, IL

20h•Remote

About The Position

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.

Requirements

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
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
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

Nice To Haves

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

Responsibilities

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
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
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
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
Other duties as assigned.