Founding Account Executive

Founding Account Executive

Location: Remote (US-based, travel required) | Reports to: Founder & CEO | Start: Summer 2026

About EnlightenAI

EnlightenAI is an AI-powered writing assessment platform for K–12 schools and districts. We enable teachers and leaders to calibrate an AI to score and give feedback on student writing more accurately than two human graders working independently. We work with some of the biggest and most prominent charter networks and districts in the country, backed by NewSchools Venture Fund, Teaching Lab Studio, Charter School Growth Fund, and other prominent impact investors. We're a small team, well-funded, and growing fast. This is a ground-floor role.

Why This Role Exists

EnlightenAI is at an inflection point. We've built a product that schools love, landed marquee customers, and proven strong retention. Now we’re building a repeatable, systematic go-to-market engine to grow our footprint across charter networks and districts nationwide. This role is the foundation of that engine — you'll own the outbound pipeline, build relationships in new markets, and help us figure out what works.

What You'll Do

• Research targets, write outreach sequences, cold call, cold email, build a social media presence, and develop marketing content that earns attention in a noisy market.
• Own the customer journey from first discovery all the way through onboarding. You're the first face they see and the person who makes sure they're set up for success.
• Run demos and help support pilots — you're showing schools what the product can do and making sure early experiences convert to long-term partnerships.
• Build and maintain relationships with schools and school networks. You invest in our partners — keeping in touch, making sure things are going well, and ensuring they know they matter to us.
• Triage customer support — sometimes that's a quick answer, sometimes it's surfacing a ticket to get something fixed, and sometimes it's instructional advising where you're helping a school or district have a successful implementation.
• Build a GTM engine: test outreach channels and messaging, track and measure results, and systematically figure out what to start doing, stop doing, and change. You’re running a scientific, systematic process for building a pipeline of school partnerships.
• Own conferences end-to-end — apply for speaker slots with partners, run the booth, manage all pre- and post-event communications, and convert conversations into partnership prospects.
• Manage deals through the full cycle from first touch to signed contract, supported by the CEO.

Who You Are

• You've demonstrated tenacity in a high-rejection environment. Door-to-door sales, fundraising, recruiting, debate, competitive athletics — something where you got told "no" and kept going.
• You were a top performer in a competitive setting. You can point to specific achievements, ideally both individually and in team settings.
• Performance-based pay excites you, you’re motivated to exceed quotas
• You've been a highly effective teacher or leader inside a K-12 school, or have built deep knowledge and insight into the space another way. You understand the daily reality of a classroom, you speak the language, and educators trust you because you've been one of them.

Strong Signals of Fit

• You deeply believe the following: “I always figure it out, and I never give up.”
• You're a power user of AI tools and you're constantly, thoughtfully using them to boost your own output.
• You've sold something before, even informally. You know what it feels like to close a deal.
• You're comfortable with long days. This is a startup. We enjoy working hard and seeing the impact.
• You're organized and data-driven. People who work with you would describe you as highly reliable.
• You have impeccable communication. You don't just say a lot, you select your words thoughtfully, you proofread your work, and you are good on your feet.
• You're extremely quick on follow-up and diligent about tracking it so nothing slips through the cracks.
• You're deeply open to feedback and learning. You never make the same mistake twice.
• You’re good at managing expectations. You'll get bug reports, feature requests, and customer feedback constantly — you can prioritize and respond thoughtfully rather than reacting impulsively to the last thing someone told you.
• You have a high locus of control. When the going gets tough, you won’t make excuses or give up.

Compensation & Benefits

• Base Salary: $65,000 – $85,000 depending on experience
• Commission / OTE: $120,000 OTE. Uncapped commission on new business. Structure designed so a strong performer meaningfully out-earns base.
• Equity: Stock options with 5-year vesting and 1-year cliff. This is a ground-floor grant — meaningful upside if the company grows.
• Health: Monthly health insurance stipend. We're a small startup — no group plan yet, but we make sure you're covered.
• PTO: Flexible PTO. The education sales calendar has natural downtime in summer and winter, which is when we typically take breaks.
• Coaching: Weekly 1:1 with the CEO plus ongoing coaching from an external sales advisor. You'll learn fast.
• Travel: Travel expenses covered for conferences and in-person meetings. Expect 10-12 trips per calendar year.

How to Apply

Send an email to gautam@enlightenme.ai with:

• Your resume
• A short note on why this role is the right next thing for you. Feel free to use AI to produce your best work.
• One of the following (your choice):
  • A cold outreach email you'd send to a Chief Academic Officer at a charter network who has never heard of EnlightenAI. Your goal: get a demo on the calendar.
  • A short Loom video (under 5 minutes) pitching any software product you love, OR demonstrating an AI workflow that makes you uniquely productive.