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

Inspira Financial; Oak Brook (IL); Remote; USD 120,000 - 180,000; Full time

Job summary

Inspira Financial is seeking a Manager, Mid-Market and Small Group Sales (East) to lead the East region team, spanning Mid-Market and Small Group sellers. This front-line role reports to the Senior Director and focuses on coaching, deal strategy, and pipeline discipline to elevate performance.

The position owns the East region's combined new business targets, drives weekly and monthly forecasts, and ensures CRM hygiene.

Qualifications

• Leadership of a combined East region Mid-Market and Small Group sales team.
• Experience coaching and developing sellers across multiple segments.
• Ability to set and monitor regional targets and forecasts.

Responsibilities

• Coaches the East region team across both Mid-Market and Small Group sellers.
• Owns onboarding, ramp, and time-to-first-sale for new sellers.
• Delivers accurate weekly and monthly forecasts for both segments.
• Maintains CRM hygiene and regional activity standards across Salesforce environments.
• Attends events to grow Inspira’s footprint and collaborates with HR & Sales Enablement.

Skills

Team leadership

Coaching & development

Forecasting & analytics

CRM skills

Sales strategy

Tools

Salesforce

Job 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