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

Inspira Financial Trust, LLC; Oak Brook (IL); Remote; USD 90,000 - 135,000; Full time

Job summary

Inspira Financial Trust, LLC in Oak Brook, IL, seeks a Manager, Mid-Market and Small Group Sales (West) to lead a combined West region team of 10–12 direct reports across Mid-Market and Small Group segments. The role focuses on coaching, pipeline discipline, and fast feedback to raise seller performance.

You will own the West region’s new business target, drive forecast accuracy, onboard new sellers, and partner with Sales Enablement to implement plays and AI-assisted selling tools.

Qualifications

• Leads and coaches a combined West region team across two segments.
• Sets and enforces regional activity standards and CRM hygiene.
• Partners with HR on performance and recruiting.

Responsibilities

• Coaches the West region team across Mid-Market and Small Group through weekly 1:1s, deal strategy sessions, call coaching, and pipeline reviews.
• Owns onboarding, ramp, and time-to-first-sale for new sellers in both segments, with Sales Enablement.
• Drives adoption of sales plays and AI-assisted selling tools in live selling.
• Owns the West region's combined new business target and delivers forecasts for both segments.
• Attends broker and finalist meetings in a coaching capacity rather than as the primary seller.
• Participates in recruiting, interviewing, hiring, and onboarding for the region.
• Supports broker/consultant relationships and regional events to grow Inspira's footprint.

Skills

Leadership

Coaching

Sales strategy

Forecasting

Tools

Salesforce

Job description

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