Project Management Officer
$400,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Fully-remote
Any country
full-time (40 hrs/week)
Flexible schedule
Long-term role

Project Management Officer   $400,000 USD/year

Description

EdTech is drowning in wasted spend and weak outcomes. Despite billions over dollars getting poured into education technology, most organizations struggle to measure impact, optimize vendor performance, or even get a clear view of what’s working. Procurement is reactive. Tools don’t talk to each other. Stakeholders are flying blind. The result? A bloated tech stack, vendor sprawl, and students left behind.

2 Hour Learning is building something different: an AI-first command center for education investments. We’re redesigning the PMO from the ground up—not as a compliance function, but as a strategic, data-fueled force that drives execution, accountability, and academic results. With $50M in EdTech initiatives under management and direct access to founders and execs, this role is about building a system of truth, rigor, and velocity using AI-powered tools, automated reporting, and ruthless prioritization. The goal is to make sure every dollar spent improves outcomes for learners.

This role is for someone who wants to run the machine. You’ll architect the processes, oversee the tools, hold vendors to account, and force clarity where ambiguity reigns. You’re not a back-office project manager—you’re a strategic operator with teeth. You’ll be negotiating contracts, reallocating work based on scorecard data, and flagging execution risks before anyone else sees them. If you need step-by-step instructions, this won’t be a fit. If you can see the system and drive it forward, it’s yours to own.

You’ll report directly to leadership, work closely with the founder and cross-functional teams, and lead the transformation of how we manage and grow our EdTech portfolio. If you’re obsessive about clarity, allergic to fluff, and ready to leave a mark on education outcomes, we want to meet you.

What you will be doing

  • Regularly assess the 25+ EdTech initiatives, working with vendors and internal stakeholders to define, maintain, and validate educational outcomes
  • Design and implement processes, reports, and AI-driven tools to track progress, enforce accountability, and provide transparency on commitments
  • Develop and maintain a vendor scorecard, assess vendor strengths, reallocate projects to the best-fit vendors, and identify gaps where new vendors are needed
  • Establish and run a structured dual-bid process for new approved initiatives to ensure strategic vendor selection and cost-effective contracting

Key responsibilities

  • Develop and take full ownership of a centralized tracking and management system for a $50M EdTech portfolio

Candidate requirements

  • 10+ years of experience in Program Management, Portfolio Management, or PMO Leadership, overseeing large-scale, multi-initiative portfolios
  • Experience managing $25M+ technology budgets, ensuring strategic allocation and ROI
  • Expertise in vendor management & contracting, including competitive bidding, contract negotiation, and performance optimization
  • Experience implementing centralized tracking & reporting systems, preferably AI-driven (e.g., Linear, Jira, Asana, or similar)
  • Strong executive stakeholder management skills, with a track record of influencing C-suite decision-making
  • Experience leveraging AI for process automation & analytics, driving efficiency and strategic insights

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Pass Cognitive Aptitude Test.
STEP 1

Pass Cognitive Aptitude Test.

Pass English Proficiency Test.
STEP 2

Pass English Proficiency Test.

Prove Real-World Job & AI Skills.
STEP 3

Prove Real-World Job & AI Skills.

Ace An Interview Or Two.
STEP 4

Ace An Interview Or Two.

Accept Job Offer.
STEP 5

Accept Job Offer.

Frequently asked questions

About Crossover

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.