Inspira Financial is your devoted health, wealth, retirement, and benefits administrator. We work with organizations and individuals to navigate paths towards a better future and turn everyday actions into life-changing impact.  

We believe that together, we have the power to enrich lives. We take on the incremental, the complex, and the time-consuming—providing solutions that strengthen and simplify the health and wealth journey.    
  
Inspira Financial is the brand name used for products and services provided by one or more of the Inspira Financial group of companies, including Inspira Financial Trust, LLC (formerly known as Millennium Trust Company, LLC) and Inspira Financial Health, Inc. (formerly known as PayFlex Systems USA, Inc.).   

Retirement and custody services are provided by Inspira Financial Trust, LLC and consumer directed benefits are administered by Inspira Financial Health, Inc. Inspira Financial Trust, LLC and Inspira Financial Health, Inc. are affiliates. Inspira Financial Trust, LLC and its affiliates perform the duties of a directed custodian and/or an administrator of consumer directed benefits and, as such, do not provide due diligence to third parties on prospective investments, platforms, sponsors, or service providers, and do not offer or sell investments or provide investment, tax, or legal advice. Inspira and Inspira Financial are trademarks of Inspira Financial Trust, LLC.    

Inspira Financial

Inspira Financial is your devoted health, wealth, retirement, and benefits administrator.

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. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by 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.

 Remote status and role locations are subject to change, and relocation is not provided.

Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to work in-office a minimum of 4 days per month from 10 am to 2 pm, with at least one day falling on a Monday or Friday. This requirement does not apply to support specialist positions.

Job Summary & Responsibilities

The Senior Director, Head of Sales Enablement will report to the President, Health & Benefits. This role owns how the H&B go-to-market organization learns, sells, and improves - standing up onboarding and field readiness, content and proposals, partner enablement, AI-driven productivity, and the systems, reporting, and metrics that run the function. Inspira’s enablement function is early in its maturity, so this is a builder’s and player-coach role: the Senior Director both sets the strategy and does the work, and hires, coaches, and energizes a team that is still being formed. Partnering closely with Sales, Partnerships, and Account Management leadership, this leader equips sellers and channel partners alike to execute Inspira’s H&B growth strategy - revitalizing distribution, deepening cross-sell, and repositioning Inspira from benefits administrator to consumer-driven health and wealth infrastructure. Success is measured in outcomes - shorter ramp, higher quota attainment, and stronger channel penetration and win rates.

Duties & Responsibilities

Onboarding, Training & Field Readiness

 Owns onboarding and ramp for all new GTM hires - sellers, partnerships, and account management - with milestones, certification, and ramp targets that shorten time-to-productivity Runs a year-round learning curriculum across product, platform, and segment-specific selling (SMB, Mid-Market, and Enterprise), and readies the field for the First Dollar platform migration Establishes demo and product certification, and equips frontline managers with coaching frameworks, call-review, and deal-inspection tools

Content, Proposals & Competitive Intelligence

 Builds and governs the sales content system - pitch decks, one-pagers, battle cards, ROI tools, and templates - and the knowledge management systems that put the right information in front of sellers at the right moment Develops and maintains sales playbooks that align process and messaging across the buyer journey Translates Marketing’s positioning and messaging into field-ready tools - talk tracks, pitch certification, and objection handling - and verifies the message shows up in live selling Partners with Product and Technology to reflect product and platform updates in internal and external collateral Leads the RFP and proposal function, maintaining a scalable response knowledge base and partnering with Sales and Marketing to strengthen GTM materials and improve win rate Arms the field with competitive intelligence to position Inspira against alternatives Collaborates with Marketing to ensure alignment between marketing campaigns and broader H&B GTM strategy, maximizing lead conversion and client engagement

Partner & Channel Enablement

 Equips brokers, consultants, and National Accounts partners with the tools, training, and second-sell capability to prioritize and sell Inspira’s suite Partners with Sales and Marketing on broker enablement and incentive programs that make Inspira the easiest suite for partners to sell

AI & Sales Productivity

 Owns the rollout and adoption of AI tools (including Claude) across the GTM organization - prompt libraries, AI-assisted workflows, and certification - for account research, call prep, proposal generation, and follow-up Tracks and grows the ROI of AI in sales (hours saved, proposal velocity, win-rate lift, cost-to-serve), and keeps AI use within Inspira’s data and governance standards

Systems, Reporting & Metrics

 Owns sales analytics and performance reporting that support leadership decision-making and day-to-day sales management Drives consistent, effective use of CRM across the sales organization in partnership with Technology Runs the enablement operating rhythm - intake, prioritization, launch calendar, and feedback loops - and leads change management for GTM initiatives Supports the evolution of H&B go-to-market strategy, helping define and prioritize the initiatives that maximize Inspira’s rate of growth Other duties as assigned.

People Leader Responsibilities

 Manages a team of 8-12 directs/indirect to achieve results. Assesses, integrates, and develops a team, including talent joining through acquisition and internal transfer. Provides regular and timely feedback, sets performance goals, and supports professional growth. Leads hiring and training processes to cultivate a high-performing team. Directs the daily workflow of the team/department.

Preferred Qualifications

Education & Experience:

Minimum Required

 12+ years of experience in sales enablement, sales operations, or go-to-market, including 4+ years leading teams Bachelor’s degree in Business, Marketing, Healthcare, or a related field, or an equivalent combination of education, experience, and training, required

Additional Preferred

 Experience in health and benefits, insurance, or financial services go-to-market preferred Experience enabling channel partners - brokers, consultants, or distributors - to sell preferred Applied experience deploying AI or LLM-based tools to a sales organization preferred

Skills & Abilities

 A builder who has stood up or scaled a function, and a player-coach comfortable both leading and doing A talent magnet who can recruit, develop, and inspire a growing team Proven track record building onboarding, training, playbooks, and content that measurably improved sales performance Expertise in optimization and deployment of sales technologies, such as: CRM (Salesforce/HubSpot), engagement (Outreach/Gong/SalesLoft), RFP support (Loopio), lead qualification (ZoomInfo, LinkedIn Sales Navigator) Deep understanding of the health and benefits sales process, including broker/consultant and National Accounts distribution Ability to translate product, positioning, and competitive insight into clear, field-ready messaging Strong content strategy and governance instincts, with comfort using Salesforce and BI/analytics tools Highly organized, with the ability to run multiple initiatives simultaneously without losing the thread Strong executive presence and communication skills; comfortable operating with ambiguity and building in a still-forming organization

Other Requirements 

Infrequent travel (20%)Ability to provide personal transportation from time to timeOccasionally lifts up to 25 poundsProlonged periods of sitting at a desk and working on a computer
Pay Range

$190,000-$220,000 per year

Compensation & Benefits

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.

Sr. Director, Head of Sales Enablement (Remote)

What the job involves