Head of Compliance Operations, 2 Hour Learning (Remote) - $200,000 / year USD

Head of Compliance Operations, 2 Hour Learning (Remote) - $200,000 / year USD

1 day ago Be among the first 25 applicants

This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$100.00 / hr - $100.00 / hr

A law degree is not required — but you must be the person Legal turns to when they need answers.

This role is not centered on policy development. It is centered on authorization. You will be responsible for enabling new school launches by obtaining regulatory clearances required for every campus to begin operating.

You will own the full scope of work — from entity formation filings to license acquisition to securing specialized exemptions — that authorizes lawful operation in all 50 states.

AI-powered tools such as a RAG Bot will help you produce jurisdiction‑specific guidance documents and process filings faster than ever, but you remain the critical reviewer who identifies ambiguity, surfaces red and yellow risks, escalates obstacles, and drives decision‑making. While strategy discussions continue, you will be delivering outcomes.

You will test and optimize intelligent workflows, update live tracking systems, and ensure nothing is overlooked. The infrastructure you create will serve as the authoritative reference for legal, operations, and leadership.

This is not a support function. It is a frontline execution role — demanding velocity, accountability, and applied regulatory expertise. You will not simply maintain existing operations. You will architect the foundation.

What You Will Be Doing

• Produce AI‑enhanced legal research briefs that convert complex, fragmented regulatory structures into actionable go / no‑go guidance — delivered within 48 hours.
• Prepare and file jurisdiction‑specific submission packages — exemption requests, licensing documentation, and legal entity records — ensuring all dependencies are satisfied.
• Monitor every approval status in real time via dashboards you manage (such as Airtable, Klair, Retool), flagging obstacles and setting automated alerts ahead of key deadlines.
• Resolve edge‑case denials, navigate multi‑state discrepancies, and take full ownership of the compliance endgame — from initial submission through final approval signature.
• Iteratively improve the AI and automation infrastructure by evaluating outputs, designing new workflows, and deploying updates that enhance precision and turnaround time.

What You Won’t Be Doing

Head Of Compliance Operations Key Responsibilities

Obtain and uphold the regulatory authorizations required for 2 Hour Learning to launch and operate educational institutions nationwide — by building, managing, and executing technology‑driven compliance frameworks that function at scale.

Basic Requirements

Nice‑to‑have Requirements

About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one‑size‑fits‑all model and replacing it with AI‑driven personalized learning that helps kids master academics in just two hours a day.

With students consistently ranking in the top 1‑2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter.

They offer a dynamic, on‑campus and remote‑friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

2 Hour Learning is reprogramming learning for the AI era.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full‑time (40 hours per week), long‑term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD / hour, which equates to $200,000 USD / year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com / help-and-faqs for more details on this topic.

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