Leads and builds Inspira’s sales enablement function for its Health & Benefits go-to-market organization. Owns onboarding, training, field readiness, sales content, proposals, partner enablement, competitive intelligence, AI productivity, CRM adoption, analytics, reporting, and change management. The role develops enablement strategy, improves ramp and sales performance, manages a team of 8–12, and partners with Sales, Marketing, Product, Technology, Partnerships, and Account Management to drive growth and channel effectiveness.
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:
Compensation & Benefits
$190,000-$220,000 per year
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 time
- Occasionally lifts up to 25 pounds
- Prolonged periods of sitting at a desk and working on a computer
Compensation & Benefits
$190,000-$220,000 per year
Inspira Financial Denver, Colorado, USA Office
Inspira Financial Accruit an Inspira Financial Solution Office
44 Cook St Suite 530, Denver, Colorado, United States, 80206
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