Account Executive, Chicago (Train in Austin, Return to Launch) (Chicago)

Subject is hiring Account Executives in Austin, and we're recruiting hard out of Chicago. Save on taxes, save on rent, and live somewhere new for a year and a half.

Subject is considering an office launch in Chicago, in 2028, and you'd have the option to be part of the founding team there. Subject has a large footprint in the midwest with our customers, so the city is a prime contender for the next office launch. Some people will fall in love with Austin and stay. That's a great outcome too. But if getting back to Chicago is the goal, we'd love to have you on that founding team.

The ideal candidate has strong sales, interpersonal, and organizational skills, plus real hustle. You're comfortable juggling a lot at once and know how to manage your time to hit your number.

Compensation: $500K+ earning potential

Forget the infamous OTE. At Subject, we show you real numbers, real contracts, real math. Based on current pacing, multiple AEs will make over $500K this year.

The majority of the team is still within their first year at Subject and their first year in a new territory. Late-stage candidates will be shown actual rep performance and earnings.

LinkedIn Top 40 U.S. Startups (2025) | Named one of America's Top EdTech Companies by TIME & Statista (2026)

Start date : September and October 2026 cohorts.

BEYOND YOUR APPLICATION

The moment you apply, you're being evaluated. We hire on habits and behaviors, because habits and behaviors come before performance. Applicants are expected to show us theirs instead of telling us about them:

• DM the hiring manager. If you can't find and reach the right person at a company that's hiring you, you won't find the right person at a 30,000-student district.
• Multithread our leadership. The AEs who win here align 3+ stakeholders to close a deal. Run that play on us — thoughtfully, not spam.
• Show speed-to-lead. How fast and how sharp you follow up with us is how fast and how sharp you'll follow up with a superintendent.

Everything you do in this process is a signal.

Location : Based in our Austin, Texas HQ. In-office 5 days a week, and some weekends required. Candidates outside Austin must relocate prior to start. Subject will not cover relocation fees.

Travel : Up to 60% of the month at certain times of the year, in-territory, with generous travel stipends.

WHAT WE OFFER:

• An aggressive, uncapped commission plan — top performers see significant upside
• Comprehensive health, dental, and vision benefits
• Stocked kitchen with a variety of breakfast items, coffee, snacks, drinks
• Lunch and Dinner provided daily
• $100/month toward gym membership
• 90-min wellness break Monday-Thursday
• 10% salary increase when you live within 1.5 miles of our office
• Flexible PTO
• The opportunity to sell a revolutionary product that is obviously better than anything else in K12, one that students and teachers actually love using, that makes a real positive impact on communities and the world
• The personal and professional growth that comes from applying yourself to a company growing this fast

WHY NOW?

Most job posts want you to start in two weeks. This one doesn't, and that tells you who we're hiring.

The best AEs we know are employed, mid-year, and on pace. They're not walking away from an H1 commission check, and we'd worry about them if they would. A Fall start means you finish your year strong, collect what you've earned, and leave clean.

It's also when the K-12 sales calendar actually begins. You'll ramp during the Fall, build pipeline through budget season, and close through Spring and Summer — a full cycle, timed right, instead of joining mid-stream and inheriting someone else's half-built quarter.

If you're reading this from a seat where you're winning but the ceiling is visible, this timeline was designed for you.

WHAT THIS ROLE ACTUALLY IS

You will be the CEO of your territory and own it end-to-end: from prospecting and first conversation to signed contract, SMB through Enterprise. You'll multithread superintendents, curriculum directors, CTOs, and CFOs, build Mutual Action Plans and relentlessly progress deals, navigate procurement vehicles, and negotiate contracts that protect margin and the partnership.

District sales happen in-person, at central offices, board meetings, conferences, on-site demos. You'll spend big stretches of the month across your territory, at events and conferences, and the rest in our Austin office with your team. You will be the face of Subject to district leaders nationwide, and the quality of your process and presence directly shapes how we grow.

What you're selling: AI-powered, personalized education at scale, including cinematic, short-form video courseware built for the generation raised on the best consumer media, paired with a learning platform serving thousands of students daily. Your prospects span the full diversity of K-12: districts serving 40,000+ students down to sub-200-student rural systems.

THE SCOUTING REPORT

Who you are:

• You know your numbers cold. Quota, attainment, pipeline coverage, average deal size, win rate — without checking. You've personally closed $1M+ ARR years in complex, multi-stakeholder B2B (SaaS, pharma, medical — same long-cycle, field-heavy, relationship-driven motion).
• You love being in the field. You'd rather drive three hours face-to-face with a superintendent than send a fourth follow-up email. A room of 5, 50, or 500 doesn't change your heart rate, at least not on the outside.
• You run the deal like you own it. No blaming lead quality or product for the gap. Clear next steps and accountable timelines on every opportunity. A busy week with a flat forecast is a problem you own. There are no bystanders here — if something's broken, you fix it or grab someone who can.
• You tell the truth early. To prospects, that the timeline isn't realistic, the budget doesn't match the scope, another vendor fits better. You'd rather lose fast and honestly than win on a story that collapses at renewal.
• You're AI-native. Claude, Gong, Salesforce are already in your workflow — prepping district meetings, drafting personalized outreach, pristine pipeline hygiene, pattern-matching your book. Not curious about AI. Already operating with it.
• You make your teammates better. We're a team with a head coach, coaches, and players — not a family. You coach hard, take real-time feedback without flinching, and share what's working instead of hoarding it. All-stars don't coast alone; they elevate others.
• You're an all-weather competitor. A prospect reply on Saturday gets an answer on Saturday, because you treat your pipeline like your business. Mid-deal, you don't go dark.
• You're a grinder. 60+ hours a week is the commitment (you're probably already doing this now), and you bring it because the work is the reward, not the obligation. You're in the office and in the field by default — we don't beg, chase, or remind. If we have to push you to take initiative, this isn't the seat for you.

Who you are not:

• A Zoom seller who calls travel client-facing time but hasn't left their home office in a year
• An activity reporter — calls dialed and demos delivered, but the forecast never moves
• Someone who needs an SDR, a warm lead, and a playbook before they'll pick up the phone
• A knowledge hoarder or politics player — if your instinct is to protect your lane instead of the team's outcome, you won't last here
• Someone who pushes personal agendas at work — we stay apolitical, always: we support all kids, we don't take sides, and we show up every day to help students grow no matter where they come from or what they believe
• Someone who's uncomfortable living in public — we're a company that posts a lot and welcomes critics; you have to be okay with that
• Someone who hears 5 days in Austin, 60% travel, 60+ hour weeks during peak cycles and starts negotiating the premise

We're not looking for people who can tolerate the bar. We're looking for people who set it higher than we do.

Bonus points

• Former K-12 educator who moved into B2B sales — you can read a STAAR report or a TEKS gap and turn it into a sales motion
• AI already in your sales workflow — if you've built your own prompts, agents, or automations for prospecting, prep, or pipeline review, tell us about it
• Experience in early-stage startup sales orgs that experienced hyper-growth
• History of multiple promotions within the same company

WHO WE ARE

At Subject, we're a rapidly-growing Austin-based team empowering a global community of students with access to on-demand, delightful learning that truly engages. We're racing to re-imagine what's possible in the classroom, bringing solutions that do real work alongside educators, and we want you on this team.

Vision : Revolutionize education by building the best product for acquiring valuable, fulfilling skills while empowering educators to work efficiently and joyfully.

Mission : Maximize the potential of all learners and educators, regardless of zip code.

Core Values:

• Education Obs]]>