About SchoolAI

SchoolAI is an AI-powered platform built for K–12 education, designed to help teachers personalize learning, reduce administrative burden, and give every student a more meaningful experience in the classroom. We’re a fast-growing EdTech company on a mission to make great education more accessible — and we’re building the revenue org to match.

Our GTM team spans Sales, Customer Success, Revenue Marketing, Field Marketing, Implementation, and Government Relations. We move fast, we care deeply about the educators we serve, and we’re looking for people who bring both rigor and heart to the work.

Values

We want everyone at SchoolAI to make a competitive wage, have fun, and do good. As we build out the team, we optimize for, and invest in, great people who:

• 🪄 Make Magic: You're making magic when you dream big, sweat the details, make the complex look elegant, and the final result is one that puts a smile on everyone's face. People are drawn to working with you and your work.
  
  
• ☀️ Rise to the Moment: You're rising to the moment when you show up, answer the call, make the extra effort, and appreciate the fact that we are working with the coolest technology, in the biggest space it’ll impact, and we’re in pole position.
  
  
• 🔗 Connect the Dots: You've done the work to prioritize, understand, and tie your work to your team, to students, and to the people who support them. You're driving tangible outcomes and can connect your work to meaningful, tangible business results and goals. You're connecting the dots when you've thought deeply and have a throughline narrative for your work.
  
  
• 🚀 Make High Leverage Bets: Always consider the board in front of you – using data, instinct, honed expertise, and user problems to pick the best move and maximize the impact of every resource. When the moment is right – go all in.
  
  
• ➡️ Simplify and Go: Cut through the noise. Focus on what’s essential and act with urgency. Speed is your ally, simplicity your tool. Embrace clarity and let it guide you to swift victories.

We use our core values to make decisions, evaluate work, and win. We expect that every team member demonstrate these values. In turn, we'll invest in you and your impact at SchoolAI.

About the role

We are at an inflection point. Our pipeline is growing, our product is evolving rapidly, and our revenue team is executing at a high level across every function. What we’re missing is the connective tissue — someone whose entire job is to make sure everything we build, launch, and teach actually lands and sticks.

The GTM Enablement Leader will be the first dedicated enablement hire at SchoolAI. This is a strategic leadership role — not a support function. You will report directly to the Chief Revenue Officer, hold a seat at the GTM leadership table, and work in close partnership with Sales, Customer Success, Product, Field, and Revenue Marketing. Your work will have direct and measurable impact on revenue outcomes.

What you'll own

Enablement Hub

• Build and maintain a unified, well-resourced Enablement Hub accessible to the full GTM org — Sales, Customer Success, and Subject Matter Experts. This is the single source of truth for decks, talk tracks, objection handling, product knowledge, and certification materials. The Hub exists to ensure that every person on our revenue team is telling the same story, with the same confidence, regardless of role or region.
• 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. From a sales rep’s first outreach to a CS leader’s renewal conversation, the story should feel like one company.

Enablement Calendar

• Own the GTM enablement calendar end-to-end, built in partnership with our 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) so that delivery doesn’t fall to senior leaders by default.
• Drive demo and pitch certification programs so that reps are practicing before they’re live, not learning in front of customers.

Call Review & Coaching Cadence

• 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 — closing the loop between what we teach and what we see in the field.
• Track objection trends across regions and work with leadership to develop timely, accurate responses.

REKS Framework & Performance Coaching

• 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, not ad hoc.
• Help managers become better coaches by equipping them with tools, frameworks, and call review insights they can use in 1:1s.

Cross-Functional Partnership

• Partner with Product Marketing to ensure new feature launches are fully enabled before they reach customers — not just announced.
• 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.

Qualifications

Required

• 5+ years in a GTM Enablement, Revenue Enablement, or Sales Enablement role — we’re looking for someone who has been in the work long enough to walk in with confidence and build from day one.
• A strong understanding of the K–12 education landscape is important to us. You must understand the K–12 education landscape, 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. Enablement at SchoolAI is a full-org role.
• Former teacher or educator background. We deeply value candidates who have classroom experience. You will be enabling people who sell to teachers, and having walked in those shoes makes a real difference.
• Demonstrated ability to build and run coaching programs, certification processes, and consistent call review cadences.
• Strong facilitation and communication skills. You are comfortable leading sessions, presenting to revenue leadership, and synthesizing complex information for different audiences.
• A builder’s mindset. You will be standing up systems and rhythms that do not fully exist yet. You need to be energized by that, not slowed down by it.

Preferred

• Experience reporting into a CRO or SVP of Revenue — you understand how revenue leadership thinks, what they prioritize, and how to communicate enablement impact in terms that matter to the business.
• Direct experience in a Sales or Customer Success role, ideally in a leadership capacity — having carried a bag, managed a book of business, or led a revenue team gives you the credibility and instinct to enable others in a way that truly resonates.
• 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, not something handed to you.

We are building something that matters. SchoolAI exists to make great teaching more sustainable and great learning more personalized — and we believe AI can be a genuine force multiplier for educators when it’s designed thoughtfully.

This role is a unique opportunity to be the first dedicated enablement leader at a company that is growing fast, has a strong product, and has a revenue team that is 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.

If you have taught in a classroom, spent years enabling revenue teams, and want to do work that connects both — this is your role.

SchoolAI is an equal opportunity employer. We welcome applicants from all backgrounds and are committed to building a diverse and inclusive team.