About The Position

SchoolAI is at an inflection point with growing pipeline, rapidly evolving product, and a high-performing revenue team. The company is seeking a GTM Enablement Leader to provide the connective tissue, ensuring that everything built, launched, and taught effectively lands and sticks. This is the first dedicated enablement hire at SchoolAI, a strategic leadership role reporting directly to the Chief Revenue Officer. The leader will hold a seat at the GTM leadership table and partner closely with Sales, Customer Success, Product, Field, and Revenue Marketing, with their work directly impacting revenue outcomes. SchoolAI exists to make great teaching more sustainable and great learning more personalized, believing AI can be a genuine force multiplier for educators when designed thoughtfully. This role offers a unique opportunity to be the first dedicated enablement leader at a fast-growing company with a strong product and a revenue team ready to be enabled. You will have direct access to the CRO, a seat at the GTM leadership table, and the resources to build something that scales.

Requirements

  • 5+ years in a GTM Enablement, Revenue Enablement, or Sales Enablement role.
  • A strong understanding of the K–12 education landscape, including the buying cycles of districts and schools, and the nuances of selling to educators.
  • Experience working across Revenue Teams (Sales, Customer Success, and Subject Matter Experts), not just supporting one function.
  • Former teacher or educator background.
  • Demonstrated ability to build and run coaching programs, certification processes, and consistent call review cadences.
  • Strong facilitation and communication skills, comfortable leading sessions, presenting to revenue leadership, and synthesizing complex information for different audiences.
  • A builder’s mindset, energized by standing up systems and rhythms that do not fully exist yet.

Nice To Haves

  • Experience reporting into a CRO or SVP of Revenue.
  • Direct experience in a Sales or Customer Success role, ideally in a leadership capacity.
  • Familiarity with HubSpot CRM and experience building enablement resources within or alongside a CRM workflow.
  • Experience with AI-powered tools in an educational or sales context.
  • Comfort operating in a high-growth, fast-moving startup environment where priorities shift and clarity is sometimes something you create.

Responsibilities

  • Build and maintain a unified, well-resourced Enablement Hub accessible to the full GTM org (Sales, Customer Success, and Subject Matter Experts) as the single source of truth for decks, talk tracks, objection handling, product knowledge, and certification materials.
  • Ensure the Hub stays current as the product evolves, the competitive landscape shifts, and new plays are deployed.
  • Champion unified messaging across the full revenue org, ensuring SchoolAI enters every market, segment, and conversation with a cohesive, consistent voice.
  • Own the GTM enablement calendar end-to-end, built in partnership with Sales and Customer Success leaders.
  • Sequence what gets taught, when, and to whom, coordinating across product launches, seasonal selling moments, onboarding milestones, and coaching cycles.
  • Lead or co-facilitate GTM learning sessions (e.g., GTM All Hands, seasonal bootcamps, regional enablement).
  • Drive demo and pitch certification programs so that reps are practicing before they’re live, not learning in front of customers.
  • Stand up and own a consistent call review cadence across Sales and Customer Success, listening to calls regularly, identifying patterns, and surfacing what’s working and what’s not.
  • Translate call insights into actionable coaching, targeted training, and updated enablement materials.
  • Track objection trends across regions and work with leadership to develop timely, accurate responses.
  • Support the Results, Effort, Knowledge, and Skills (REKS) framework used across the revenue org to assess rep performance and identify coaching opportunities.
  • Partner with Sales and CS leaders on gap identification and build targeted enablement to close those gaps systematically.
  • Help managers become better coaches by equipping them with tools, frameworks, and call review insights they can use in 1:1s.
  • Partner with Product Marketing to ensure new feature launches are fully enabled before they reach customers.
  • Collaborate with Field Marketing to align regional event strategy with enablement priorities.
  • Work alongside Subject Matter Experts to extract and package institutional knowledge into scalable training content.
  • Serve as the connective layer between what Product builds, what Marketing launches, and what the revenue team delivers.
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