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 maintai