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

Inspira Financial•Oak Brook, IL

5h•Remote

About The Position

The Manager, Mid-Market and Small Group Sales (East) is the front-line leader for Inspira’s East region sales team, spanning Mid-Market sales executives and Small Group representatives. The role reports to the Senior Director, Mid-Market and Small Group Sales and provides dedicated coaching and development between that leader and the field. It focuses on improving seller performance through deal coaching, pipeline discipline, structured development, and timely, candid feedback. The manager is accountable for the East region’s combined new-business results across both segments as the aggregate of team performance, rather than through a personal book. The East role mirrors a West-region counterpart, and strong performance in this role can prepare the manager for future senior sales leadership at Inspira. The manager leads a combined regional team, typically 10–12 direct reports, with team size varying according to coverage and segment mix. The role owns seller onboarding, ramp, and time to first sale in partnership with Sales Enablement; regional forecasts and sales execution; activity standards and CRM hygiene; and participation in recruiting and people management. It also supports regional broker and consultant relationships, contributes market intelligence and supports the rollout of the Small Group inside-sales motion. The typical schedule is Monday through Friday, with flexibility to work evenings or weekends when needed for client, partner, and industry engagements. Travel is required in up to 50% of weeks, typically for one or two days at a time. The manager must reside in the Pacific or Mountain time zone within the assigned region and be able to provide personal transportation from time to time. The work involves prolonged sitting and use of standard office equipment, with occasional lifting of up to 25 pounds.

Requirements

At least 7 years of sales experience in employee benefits, health and benefits, consumer directed health, or a closely related field.
At least 2 years leading, managing, or formally coaching a team of sellers.
Demonstrated experience coaching sellers in both consultative, broker-influenced and higher-velocity, transactional sales motions.
Consistent record of quota attainment as an individual contributor before moving into leadership.
Bachelor’s degree in Business, Marketing, or a related field, or an equivalent combination of education, experience, and training.
Ability to develop people and identify specific sellers who have achieved measurably better performance through coaching.
Strong deal-coaching and consultative-selling skills across transactional Small Group and multi-stakeholder, broker-influenced Mid-Market sales cycles.
Ability to conduct direct performance conversations early while maintaining the relationship.
Ability to analyze pipeline and identify the seller behaviors driving results.
Fluency with Salesforce and AI-powered productivity tools.
Must reside in the Pacific or Mountain time zone within the assigned region.
Ability to provide personal transportation from time to time.
Able to travel in up to 50% of weeks, typically one to two days at a time.
Able to work evenings or weekends as needed for client, partner, and industry engagements.
Able to sit for prolonged periods and operate standard office equipment; occasionally lift up to 25 pounds.

Nice To Haves

Experience with consumer directed health products such as HSA, FSA, HRA, or COBRA.
Experience selling or leading in a broker- and consultant-influenced market.
Experience leading a team through a coverage-model or operating-model change.

Responsibilities

Coach East-region Mid-Market and Small Group sellers through weekly one-on-ones, deal strategy sessions, call and meeting coaching, and pipeline reviews.
Adapt coaching to the higher-velocity, transactional Small Group sales cycle and the longer, broker-influenced, multi-stakeholder Mid-Market sales cycle.
Help sellers build and refine outreach cadences across both segments.
Own onboarding, ramp, and time to first sale for new sellers in partnership with Sales Enablement.
Drive adoption of sales plays, messaging, and AI-assisted selling tools in live selling.
Own the East region’s combined Mid-Market and Small Group new-business target as the aggregate of team quotas, and deliver accurate weekly and monthly forecasts for both segments.
Inspect and progress deals, and attend key prospect, broker, and finalist meetings in a coaching rather than primary-seller capacity.
Set and uphold regional activity standards, prospecting expectations, and CRM hygiene across Inspira’s Salesforce environments.
Escalate deal-level risks and resourcing needs early.
Support regional broker and consultant relationships in coordination with the Head of Broker & Consulting Relations.
Attend local and national events alongside team sellers to grow Inspira’s market footprint.
Provide field intelligence about competitive activity, pricing pressure, and product gaps across both segments.
Contribute to rollout of the Small Group inside-sales motion in the region.
Manage a combined East-region team of Mid-Market sales executives and Small Group representatives, typically 10–12 direct reports.
Provide hands-on, credible coaching and timely, specific feedback; build development plans grounded in observed selling behavior.
Address underperformance early and directly in partnership with the Senior Director and HR.
Participate in regional recruiting, interviewing, hiring, and onboarding across both segments.
Perform other duties as assigned.