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Open nowFirst seen 5 days ago

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

Inspira Financial36 open roles

Where
Oak Brook, IL, USA
Work mode
Remote
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Your applicationOpen nowManager, Mid-Market and Small Group Sales (West Market) RemoteInspira Financial · Oak Brook, IL, USA

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The clock on this job

Early applications get read.

12.3% of postings close within 7 days. Measured by our own scanner across the market. Inspira Financial postings stay open a median of 1 days.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.3%7 days
  4. 19.3%14 days
  5. 35.6%30 days
  6. 58.1%60 days
This job: first seen 5 days ago

Inspira Financial median: 1 days open

The posting

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.

Duties & Responsibilities:

Coaching & Seller Development

  • 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

Revenue & Pipeline Execution

  • 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

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 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

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 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
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