East Regional Sales Coach — Mid-Market & Small Group

Inspira Financial Trust, LLC; Oak Brook (IL); Remote; USD 110,000 - 170,000; Full time

Job summary

Inspira Financial Trust, LLC in Oak Brook, IL seeks a Manager for East region Mid-Market and Small Group Sales to coach a combined team of 10–12 sellers. You will lead deal strategy, coaching sessions, and pipeline reviews to improve performance across longer and shorter sales cycles.

You will own the East region’s new business targets, forecast performance, and drive adoption of plays and AI-assisted selling tools while partnering with Sales Enablement and HR for onboarding, ramp, and

Qualifications

• Leadership experience coaching sales teams across multiple segments.
• Strong communication and coaching skills with performance feedback.
• Experience with CRM tools and pipeline management.

Responsibilities

• 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 reps (high-velocity, transactional) and Mid-Market reps (longer, multi-stakeholder cycles).
• Owns onboarding, ramp, and time-to-first-sale for new sellers in both segments, with Sales Enablement.
• Drives adoption of sales plays, messaging, and AI-assisted selling tools in live selling.
• 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, attending key prospect, broker, and finalist meetings in a coaching capacity.
• Sets regional activity standards, prospecting expectations, and CRM hygiene across Salesforce environments.
• Escalates deal-level risk and resourcing needs early rather than at close.
• Supports broker and consultant relationships in coordination with Head of Broker & Consulting Relations.
• Attends local and national events to grow Inspira's footprint in the market.
• Provides field intelligence on competitive activity, pricing pressure, and product gaps across both segments.
• Contributes to rollout of the Small Group inside-sales motion in the region.
• Other duties as assigned.
• Manages a combined East region team of Mid-Market sales executives and Small Group representatives; team size 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.
• Addresses underperformance early and directly, in partnership with HR.

Job description

Inspira Financial Trust, LLC in Oak Brook, IL seeks a Manager for East region Mid-Market and Small Group Sales to coach a combined team of 10–12 sellers. You will lead deal strategy, coaching sessions, and pipeline reviews to improve performance across longer and shorter sales cycles.

You will own the East region’s new business targets, forecast performance, and drive adoption of plays and AI-assisted selling tools while partnering with Sales Enablement and HR for onboarding, ramp, and