Program 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
North America
Semi-flexible schedule
Hybrid location
full-time (40 hrs/week)
Long-term role
Description
This is not an oversight role. It’s an opportunity to architect the execution layer of a movement that’s transforming education. At 2 Hour Learning, students learn twice as much in just two hours a day. But behind that simplicity is a sophisticated $50M EdTech portfolio. We’re looking for someone to build and lead the operating system that keeps it all aligned, optimized, and relentlessly focused on outcomes.
You’ll create the structure, systems, and standards that bring visibility, accountability, and velocity across 25+ high-impact initiatives. Your work won’t just ensure things get done—it will determine if we’re investing in what actually works. From defining performance metrics to enforcing a dual-bid vendor process, to owning real-time reporting powered by AI, your systems will shape strategy and surface the truth.
You’ll partner directly with founders. You’ll drive decisions with data. You’ll build a model others will want to copy. If you thrive on complexity, autonomy, and impact—and know how to translate ambition into action—this is your role.
What you will be doing
- Building a centralized, AI-driven PMO to oversee and optimize 25+ EdTech initiatives across a $50M portfolio
- Creating a vendor scorecard and reallocating work based on objective performance, not politics or promises
- Designing and enforcing a competitive dual-bid process for all new initiatives to ensure ROI and fit
- Implementing real-time tracking and reporting using tools like Linear to provide executive-grade visibility
- Driving alignment between internal stakeholders and vendors on timelines, documentation, and academic outcomes
What you will NOT be doing
- Updating spreadsheets and herding status reports by hand; this is a tech-enabled role
- Babysitting underperforming vendors with no leverage; your system gives you teeth
- Sitting in meetings wondering what’s really going on; your dashboards speak before you do
- Running a PMO that focuses on compliance instead of outcomes; yours drives real impact
- Operating with fuzzy metrics; you'll use AI to measure academic value, not just progress
Key responsibilities
Architect and lead a data-driven, AI-powered PMO that transforms a $50M EdTech portfolio into measurable academic outcomes at speed.
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
- Must be based in North America
You will be working for
Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re
About 2 Hour Learning
Quick links
How it works
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.
STEP 1
Pass Cognitive Aptitude Test.
STEP 2
Pass English Proficiency Test.
STEP 3
Prove Real-World Job & AI Skills.
STEP 4
Ace An Interview Or Two.
STEP 5
Accept Job Offer.
Frequently asked questions
Why Crossover
Recruitment sucks. So we’re fixing it.
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
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
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.
