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

Accruit; Oak Brook (IL); Remote; USD 100,000 - 140,000; Full time

Benefits offered by this job

Healthcare

401K

Paid time off

Parental leave

Employee assistance program

Job summary

Inspira Financial is seeking a Manager, Mid-Market and Small Group Sales (West) to lead a West region team from a remote, home-based setting. The role focuses on coaching, pipeline discipline, and rapid development across Mid-Market and Small Group segments.

You will drive forecasts, adopt sales plays, and mentor a team of 10–12 sellers, with Travel up to 50% and strong emphasis on broker relationships and regional growth.

Qualifications

• 7+ years of sales experience in employee benefits, health and benefits, or related field.
• 2+ years leading, managing, or coaching a team of sellers.
• Demonstrated experience coaching sellers across both transactional and broker-influenced sales.
• Bachelor’s degree in Business, Marketing, or related field, or equivalent.
• Consistent quota attainment prior to moving into leadership.

Responsibilities

• Coaches West region across Mid-Market and Small Group sellers with weekly 1:1s and pipeline reviews.
• Own onboarding, ramp, and time-to-first-sale for new sellers in both segments.
• Drive adoption of sales plays, messaging, and AI-assisted selling in live selling.
• Owns West region combined new business targets and delivers forecasts.
• Participates in recruiting, interviewing, and onboarding for the region.

Skills

Coaching

Leadership

Forecasting

Sales strategy

CRM: Salesforce

Education

Bachelor’s degree in Business/Marketing or related field

Tools

Salesforce

AI tools

Job description

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

#26-1694

Work Location Type

Home Based

Join Us!

Take the next step in your journey at Inspira Financial.Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.

Serving more than 7 million clients and representing over $62 billion in assets, Inspira partners with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners to help the people they support plan, save, and invest for a brighter future. Through solutions including automatic rollover services, health savings accounts, emergency savings, and custody services, Inspira is focused on delivering better outcomes for all. Learn more at inspirafinancial.com .

Our values shape how we show up every day. WeLead with Heartby acting with compassion, empathy, and doing what's right;Cultivate Trustthrough integrity, transparency, and accountability;Aim Higherby never settling for what's expected and continually raising the standard; andWin Togetherby collaborating inclusively to achieve the best outcomes.

Our growth and culture haven't gone unnoticed -- we've been recognized on Crain's Fast 50 and Inc. 5000 for remarkable growth, and named to Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer for our workplace culture and benefits.

Don't meet every single requirement? That's okay. We know growth comes from people who are willing to learn and challenge themselves, not just check every box. If you're energized and inspired by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, we want to hear from you. We look forward to receiving your application.

Our office locations are designed to bring people together, foster collaboration, and build meaningful connections. While some roles are based at one of our office locations, remote status and role locations are subject to change, and relocation is not provided.

Job Summary & Responsibilities

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
• 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.
• 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

Preferred Qualifications

Education & Experience:

• 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

Pay Range

$100,200-$140,000 base per year, OTE of $210K +

The compensation for this position will vary depending on factors such as your location, skills and experience. The compensation package may also include incentive and bonus opportunities.

Inspira provides industry-leading benefits including, but not limited to: healthcare, 401K savings plan, company holidays, paid time off, parental leave and an employee assistance program.

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This Company is an Equal Opportunity Employer, and does not discriminate on the basis of race, gender, ethnicity, religion, national origin, age, disability, veteran status, or on any other basis prohibited by law. Information on race, gender and national origin will only be used for statistical and recordkeeping purposes, and will not be used in making any employment decisions. All information provided will be kept separate from your expression of interest. Providing this information is strictly voluntary, and you will not be subjected to any adverse action or treatment if you choose not to provide this information. If you do not choose to answer these questions, we ask that you select "Decline to Identify" for each question. Thank you for your voluntary cooperation.

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