Hiring: Sr. Director, Head of Sales Enablement (Remote) Company: Inspira Financial Location: Oak Brook, IL Job Posted Time: 2026-09-10 13:26:39 Employment Type: Remote Target Skills & Keywords : Change Management, Content Strategy, HubSpot, LLM, Salesforce, Segment About the job Experience: •12+ years of experience in sales enablement, sales operations, or go-to-market, including 4+ years leading teams Required Skills: •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 Qualifications: •Applied experience deploying AI or LLM-based tools to a sales organization preferred •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) •Comprehensive expertise in the health and benefits sales process, including broker/consultant and National Accounts distribution •Demonstrated capacity 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 Compensation: •$175,800 - $220,000 / year •The compensation package may also include incentive and bonus opportunities Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!