Sr. Director, Head of Sales Enablement (Remote)

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. 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