Sr. Director, Head of Sales Enablement (Remote)

Inspira Financial•Oak Brook, IL

1d•Remote

About The Position

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.

Requirements

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
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
Ability to provide personal transportation from time to time

Nice To Haves

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

Responsibilities

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
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
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
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
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
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.