Sales Development Representative

Sales Development Representative (SDR)

$65–$75k base | $100-110k OTE, uncapped | Equity | Full-time | In-Person in New York, NY or Fully Remote in the US

TrueMark is the controlled environment for student AI use in education. Our monitored workspace allows teachers to control how (or if) students use AI on written assignments, and shows them exactly how every piece of work was created.

At the core, we help educators navigate the tension between AI literacy and academic integrity. If you’ve taught in the last three years, you’ve lived this: you can’t ban AI, you can’t ignore it, and you can’t grade what you can’t trust. It’s a near-universal problem that only gets worse as AI gets better, and we have no direct competitors because others have assumed it’s unsolvable.

In our first 18 months since launching, we’ve:

• Amassed almost 50 paying schools/districts from grades 4–12 and higher ed, including Phillips Exeter and Boston College

• Won a US Dept of Education grant to research and develop our AI grading and personalization features

• Inked state contracts with New York and Montana

• Raised funding from Thrive Capital (investors in OpenAI, Cursor, and Instagram), the US Dept of Education, and LearnLaunch

Students spend tens of thousands of hours writing on our platform each week. And our product works: 65% of monthly active users are weekly active, our highest-usage school saw test scores increase 18% in their first year, and roughly 80% of our pilots convert to paid contracts.

Which means the hard part isn’t winning once we’re in the room. It’s getting into the room. That’s where you come in.

Our founders, Will and Shelley, are both technical. They worked at Google and Stripe before this, and before that, they met at Brown where they bonded over creating a new Computer Science course together for their senior year capstones. Our sales team is small and senior: an account executive with eight years in edtech who has converted every pilot he’s run here, and a Head of Customer Success who did Teach for America.

Our lean team is based out of NYC. You’d be joining us at the perfect time—the part that years later, people will remember the most.

As our SDR, you’ll be the first voice a school leader hears from TrueMark. You’ll call and email curriculum directors, instructional technology coordinators, principals, and assistant superintendents, and turn cold contacts into qualified discovery calls for our sales team.

WHAT YOU’LL WORK ON

Select challenges you’ll face in your first 6 months:

• Cracking the district phone tree. Curriculum directors don’t pick up unknown numbers, and their assistants have heard every pitch. You’ll figure out which titles answer, when they answer, and what the first fifteen seconds need to sound like—with the unfair advantage that you’ve actually worked in a school.

• Making email work as well as the phone. School leaders get hundreds of vendor emails a week and open almost none. You’ll write and test sequences a school administrator would actually want to read, and learn which subject line gets an assistant superintendent to reply.

• Writing the playbook. Talk tracks that don’t sound scripted, answers to “we already have Turnitin” and “our district blocked ChatGPT,” and a map of when schools actually make decisions (hint: it’s not August). What works for you becomes how TrueMark sells.

What the day-to-day will be like:

• Most of your day is on the phone and in your inbox with school and district leaders, booking 10+ qualified discovery calls a week for our account executives and founders, with clean notes and a real handoff

• Keep the CRM honest: every call, every note, every next step

• Weekly pipeline reviews with the founders, where what’s resonating and what isn’t goes straight into how we message, sell, and build the product

• Sit in on discovery calls and demos, because we want you to learn the AE craft, not just feed it

WHERE THIS GOES

We’re not building this seat for you to sit in forever. SDR is the first rung of a sales career, and we expect this role to grow into an Account Executive seat as the team expands over the next 12–18 months. Hit your numbers and show us you can run a discovery call, and you’ll get the first shot at it.

WHO YOU ARE

You taught. Maybe English, maybe history, maybe seventh-grade everything. You know when a principal actually picks up the phone, what a curriculum director really does all day, and why a district says “not now” in October and “let’s talk” in February.

You left the classroom, but not the mission. You’ve watched AI show up in your students’ work in real time, you have strong opinions about what schools should do about it, and you want to work on that problem all day.

You’re not rattled by voicemail, gatekeepers, or someone saying they’re “not interested.” You’ve run parent-teacher conferences. You’ve taught the last period on a Friday. A curt assistant superintendent isn’t going to shake you.

You are pleasantly persistent.

You’re competitive, mostly with yourself. You’re also coachable: you want feedback on Monday and you’re doing it differently by Tuesday.

You’re organized. You ran a gradebook, a classroom, and 150 kids’ worth of parent emails at once. A pipeline is easier.

You’re a strong writer and a better talker. You could get a room of thirty fifteen-year-olds to care about a thesis statement. You can get a principal to take a twenty-minute call.

You want a career in sales, not just a job near education. You see this as the first step toward Account Executive, and maybe toward running a sales team or starting something of your own someday.

You don’t need to have sold anything before. You need to be hungry, sharp, and unafraid of the phone.

QUALIFICATIONS

• 2+ years as a classroom teacher, instructional coach, or in a school- or district-facing role

• Comfortable making a high volume of cold calls every day, and comfortable hearing “no”

• Excellent writer—you’re selling a writing tool to people who grade writing for a living

• Organized and self-managing; you can hit a weekly target without hand-holding

• Based in the US and able to work school hours across US time zones

Bonus: ELA, humanities, or writing instruction background; time in a district office or department chair role; prior SDR, recruiting, admissions, or fundraising experience; familiarity with a CRM

COMPENSATION

$65–$75k base salary with $100-110k on-target earnings an uncapped submission, plus equity and health/dental/vision benefits.

This is a full-time role that can either be in-person in NYC or fully remote within the broader US.