The posting
About Scout
Scout is the AI-native operating system for schools.
Our first product, Scout SIS, is a student information system (SIS). At its core, the SIS a database for schools to store student and staff data. Every school has an SIS, but it’s one of the lowest NPS products in the history of software. Legacy players squeeze every dollar they can out of schools by locking them into long-term contracts for products that require significant hidden add-on fees to function properly. We’re trying to change that by automating complex back-office workflows across data validation, legal compliance, and government reporting.
Our mission is to give every school -- from a 3-student school in rural Kentucky to a 30,000 student district in California -- the tools that they need to help every student flourish. We're a tight-knit team that works closely with every single one of our customers to co-build a product that they can actually love.
Scout is backed by Reach Capital, Rethink Education, Y Combinator, and the founders of YC companies like Clever, SchoolMint, Coursedog, and Slash.
About the role
You own the whole thing, from "this school has never heard of us" to "this school is live and telling other schools about it."
You build your own pipeline. There's no SDR. There's no lead queue. You'll do outbound email and cold calls, work conferences and state association events, host your own roundtables and dinners for program directors, and work referrals through our existing customers.
We'll be straight with you about the hard part: we don't have a great top-of-funnel playbook yet. If you need a proven machine to plug into, this isn't it. Conferences work well. Outbound historically hasn't worked well for us. We don't think that's because outbound can't work with this buyer, we just think that we haven't cracked it yet. Figuring that out is part of this job, and you'll have the founders and our growth team working on it alongside you.
You'll have a $20k/month budget to do whatever it takes to win deals. Go to conferences, host events, use Claude Code to build websites, you name it.
You run the full cycle. Top-of-funnel. Discovery, where you'll spend 30 minutes understanding a school's deepest pains. Demos — ours run two to three hours, because a school leadership team needs to see how their own workflows, their own reporting calendar, their own staff's days will actually work in Scout. You'll find your champion inside the school and arm them. You'll design the implementation with them: scope, timeline, data migration off whatever ancient system they're on, training, success criteria.
You stay accountable after the signature. You hand off the day-to-day work of pilots and implementations to an engineer, but the pilot landing well is still yours. You watch the milestones, catch risk early, keep the champion confident, and turn a successful rollout into a reference and an expansion.
We have a 65% intro call to annual contract conversion rate, and a 92% pilot to annual contract conversion rate, with a low-6-figure ACV. Figure out how to source your own pipeline and you'll be extremely successful.
Success will look like: three months in, you've closed your first self-sourced pilot.
This job is in our NYC office, five days a week, 9am to 7pm.
You're probably a fit if
- You have roughly 2–5 years in a closing or full-cycle sales role, and you know your numbers cold: quota, attainment, average deal size, cycle length, and drop-off at every stage of the sales process.
- A real share of your pipeline was self-sourced. We'll ask what percentage and how.
- You've learned something genuinely complicated well enough to be credible with an expert buyer who knows the rules better than you do. It doesn't have to be education-specific — technical, clinical, financial, regulatory, anything where you had to go deep.
- You can hold a room for two to three hours. The demo is almost as in-depth as a full training; you have to be able to keep people engaged.
- You're comfortable being told the playbook doesn't exist yet, and you'd rather help write it than wait for it.
- You don't care about sales frameworks or gimmicky tactics to trick people into buying; you use discovery as an opportunity to truly understand the buyer's pains and be honest with them about whether or not what you're selling could help them with that.
You don't need a decade of experience, but you need proof you can sell, and proof you can learn hard things fast.
Nice-to-have, but not required
- Selling into K-12, higher ed, government, or healthcare
- Deals above $50K with cycles over three months
- Field and conference selling, not just desk selling
- Any ability to build things, or experience with tools like Claude Code or Codex — an AE who can put together a compliance calculator or a custom ROI model for a prospect has a real edge in this market
Compensation
Quota is $1,000,000 in new ACV at steady state, ramped in your first year. Commission is 10% of first-year ACV, uncapped, with accelerators above quota, paid when a deal is signed. You'll get a guaranteed ramp payment for your first six months.
We'll offer you a choice between three packages: more cash and less equity, more equity and less cash, or somewhere in the middle.
- Base: $85,000 - $115,000
- OTE: $185,000 - $215,000
- Equity: 0.1% - 0.2%
Benefits
- Great health, dental, and vision insurance
- Lunch every day, and dinner if you're here late
- Daily commuter stipend
- Gym membership near the office
- Monthly book stipend and monthly new-tool stipend, plus a real budget to buy software for the company without a procurement fight
- Regular team offsites
- Relocation stipend if you're moving to New York for this
This job is in our NYC office, five days a week, 9am to 7pm.
Hiring process
About two weeks from first call to offer.
- 30-minute call with Noah, our CEO
- One-hour deep dive — walk us through a deal you sourced and closed, in detail, from start to finish
- Paid pipeline exercise in our office (about four hours, $500). We hand you a document outlining our top-of-funnel situation and everything we know about top of funnel so far, and you prepare a presentation on how you'd build pipeline in 60 days with a $5,000 budget, plus twenty named accounts and the actual first email or call opener you'd send. About three hours of prep, then 45 minutes presenting.
- Two reference calls
A note on work authorization
You'll need to be authorized to work in the US. For an exceptional candidate we'll consider visa sponsorship — tell us early if that's your situation.
