Vice President of Sales

Subject

AustinVP Sales, Sales$180k–$220kPosted Aug 3, 2026

Compensation: $500,000 – $750,000 OTE$180,000–$220,000 base salary + an aggressive, uncapped override on your team's production + ability to earn equity This is a hands-on, in-the-deals leadership role — tactical, close to every opportunity, with the commercial instincts to structure and win the hard ones. It is not a planning-and-frameworks seat. Your upside is tied to the reps you build: based on current pacing, multiple AEs will clear $500,000 in total earnings this year, and 25% of all our AEs are on pace to make $400,000+. Your job is to make more of them. The better your team, the bigger your number. 🏆 LinkedIn Top 40 U.S. Startups (2025) | Named one of America's Top EdTech Companies by TIME &amp; Statista (2026) Start date: Fall 2026. 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: You go where your team goes. 60%+ travel of the month at certain times of the year, in the field with your reps — district offices, board meetings, conferences, on-site demos. Generous travel stipends. What We Offer:<ul><li>comprehensive health, dental, and vision benefits</li><li>meals provided daily</li><li>stocked kitchen with coffee/snacks/drinks</li><li>$100/month toward gym membership</li><li>90-min wellness break Monday-Thursday</li><li>living proximity bonus (increase in salary for living close to the office)</li><li>flexible PTO</li><li>weekend bonuses (earn additional PTO or monetary bonus)</li><li>an aggressive, uncapped override — top leaders see significant upside</li><li>the opportunity to build a team selling 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</li><li>the personal and professional growth that comes from applying yourself to a company growing this fast</li></ul> WHAT THIS ROLE ACTUALLY ISWe don't want to talk to armchair quarterbacks. This role demands four things at once, and the bar on each is high: you can rip deals yourself, you have elite commercial sense, you can structure complex, multi-stakeholder deals, and you're an inspirational leader people run through walls for. Three of the four isn't enough. This is a step up, and we built it that way — we're hiring the leader on the way up, not the career VP looking to coast into a title. You report to the CRO and are a key pillar in building our multi-state regional cohort as we scale nationwide. You will build and lead a team of Account Executives and own your region's number end-to-end: hire the bench, run the operating rhythm, coach deals in flight, and personally step into the complex, multi-stakeholder ones when the moment calls for it. Your reps will do what you do, not what you say — so your standard becomes theirs. Day to day, you'll: coach reps through pipeline creation, multithreading, and champion development; inspect deals weekly for stakeholder alignment, risk, and next-step discipline; own regional forecasting and pacing with a no-surprises standard; run live call reviews, field observations, and joint demos; and partner cross-functionally with Marketing, Customer Success, and Product to close the loop. What your team is 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. Prospects span the full diversity of K-12: districts serving 70,000+ students down to sub-200-student rural systems. Backed by Kleiner Perkins, SoftBank Opportunity Fund, Owl Ventures, Latitude Ventures, and the CEOs of WHOOP, Cameo, and Aurora Solar. THE SCOUTING REPORTWho you are:<ul><li>You never stopped selling. In your last management role you were still structuring and closing deals alongside your team — on the pitches, in the room, not just in the debrief. You've personally closed $3M+ ARR years in complex, multi-stakeholder B2B and led quota-carrying reps to do the same. You don't coach what you haven't done, and you haven't stopped doing it.</li><li>You come from a hard commercial school. You built and sold somewhere you had to manufacture pipeline and rip deals from nothing — a startup, ideally — not ride an inbound engine or a logo everyone already trusted. You don't need to have sold education. You need to have sold something hard.</li><li>You've helped scale revenue from roughly $10M to $100M. You've lived the part of the curve we're in now — the messy, fast, build-it-as-you-go stretch — and you know what breaks and what to build at each step up.</li><li>You're ready for the step up and hungry for it. You want the VP seat because you're ready to prove you can run the whole thing, not because you're looking to coast into a title. You'd rather bet on yourself in a role that stretches you than hold a bigger title somewhere that doesn't.</li><li>You lead from the front. You'd rather fly out and sit in the room for your rep's hardest meeting than send a Slack asking how it went. A room of 5, 50, or 500 doesn't change your heart rate — and it doesn't change theirs when you're beside them.</li><li>You own the number, not the excuses. You don't blame lead quality, product gaps, or the reps for a soft forecast. A busy quarter with a flat pipeline is a problem you own. There are no bystanders here.</li><li>You build winners, you don't babysit. You raise the bar, hold the line on accountability, and develop talent that gets promoted. You recruit relentlessly — always building the bench, never a seat left cold because you waited.</li><li>You tell the truth early — to your reps, to your prospects, and to leadership. You give a no-surprises forecast even when the number is ugly. You'd rather deliver the hard truth in the 1:1 than protect someone's feelings into a missed quarter.</li><li>You're AI-native. Claude, Gong, Salesforce are already in how you lead — inspecting deals, pattern-matching across the team's book, coaching from real call data, compressing your own prep. Not curious about AI. Already operating with it, and teaching it.</li><li>You make your teammates better and you're coachable yourself. We're a team with a head coach, coaches, and players — not a family. You take real-time feedback without flinching and you give it the same way. All-stars don't coast alone; they elevate others.</li><li>You're an all-weather competitor. A deal at risk on Saturday gets your attention on Saturday, because your team's pipeline is your business. You don't go dark and you don't let your reps go dark.</li><li>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.</li></ul> Who you are not:<ul><li>An armchair quarterback — you can critique a deal but you couldn't step in and close it yourself</li><li>A pure strategist — you live in planning, frameworks, and org design from 30,000 feet, when this seat needs someone in the deals every day</li><li>A career VP coasting on the title — fluent in frameworks and QBR decks, but years removed from the last deal you personally structured and closed</li><li>A brand rider — your number came from inbound and a logo everyone already trusted, and you've never had to build a pipeline from nothing</li><li>A dashboard manager who inspects from a spreadsheet, forwards the forecast, and hasn't joined a live district call in months</li><li>A leader who takes the credit and deflects the blame — reps see it instantly and it kills the team</li><li>Someone who needs reps who are already great — if you can't develop a good closer into an elite one, this isn't the seat</li><li>A forecaster who sandbags, hides risk, or surprises leadership at the buzzer</li><li>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</li><li>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</li><li>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, and so does your team</li><li>Someone who hears "5 days in Austin, 60% travel, 60+ hour weeks during peak cycles" and starts negotiating the premise rather than the mission</li></ul> We're not looking for leaders who can tolerate the bar. We're looking for leaders who set it higher than we do — because your team will only ever be as good as the standard you actually live. Bonus points<ul><li>You've built a region or a sales team from zero inside a startup that then hit hyper-growth</li><li>You were the #1 rep before you became a leader — and your reps have gone on to be #1</li><li>Leadership experience selling into K-12 districts, higher ed, or other complex public-sector buyers</li><li>AI already in how you coach and inspect — if you've built your own prompts, agents, or automations for forecasting, deal review, or rep enablement, tell us about it</li><li>A history of getting promoted, and of promoting the people under you</li></ul> WHO WE AREAt 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.