Sr. Director, Head of Sales Enablement (Remote)

Search jobs Explore companies Join talent network Talent Sr. Director, Head of Sales Enablement (Remote) IF Inspira Financial Sales & Business Development Oak Brook, IL, USA Posted on Sep 10, 2026 Apply now 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. Apply now See more open positions at Inspira Financial