Principal Program Manager $200,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Description
You've built dashboards. Tracked milestones. Chased vendors. Flagged risks. But your reports hit a ceiling. You weren't the one making the calls.
At 2 Hour Learning, that ends. We're building the most efficient, AI-powered learning system in the world—compressing a full school day into two hours without compromising outcomes. Behind that vision sits a $50M portfolio of fast-moving EdTech initiatives. Your work will decide whether those initiatives ship on time, on budget, and at quality.
You'll operate the execution engine that drives vendor performance. Maintain real-time dashboards executives trust. Own vendor scorecards that lead to action. Run structured bid processes and validate every dollar billed. If a vendor misses, you catch it. If an invoice is off, you flag it. Your work doesn't support decisions—it drives them.
This is the job for operators who want ownership, not observation. If you're ready to step into a role where accuracy matters, AI is your copilot, and your work directly shapes which vendors stay, scale, or go, we want to hear from you.
What you will be doing
- Maintain live, AI-powered dashboards across 25+ initiatives—ensuring accuracy, visibility, and timeline enforcement
- Run vendor check-ins, build rubric-based scorecards, and surface insights that drive scope cuts, reallocations, or offboarding
- Assemble dual-bid procurement packages with structured comparisons and clear scopes—supporting vendor selection
- Track contract and invoice integrity—ensuring every dollar aligns to deliverables, caps, and signed documentation
- Use AI daily to detect anomalies, draft reports, chase updates, and power all your outputs
What you will NOT be doing
- Sitting in meetings while initiatives slip quietly behind the scenes
- Delegating AI work to analysts or waiting for others to keep tools up to date
- Letting billing errors or vendor slippage go unflagged
- Producing status updates that inform no decisions and drive no action
- Relying on guesswork or feel—your outputs are evidence-backed and exec-ready
Key responsibilities
Produce the dashboards, scorecards, bid packages, and contract controls that power a $50M execution engine and drive real-time vendor accountability.
Candidate requirements
- Owned execution of a multi-initiative program or portfolio ($5M+ scope), with direct vendor involvement
- Built and maintained dashboards, scorecards, or tracking systems executives relied on—not just internal teams
- Experience running vendor check-ins, drafting bid packages, and supporting contracting cycles
- Working knowledge of contracts, SOWs, and invoices—with ability to catch and flag misalignment
- Strong written communication—your memos lead to decisions, not more meetings
- Daily use of AI tools to automate, analyze, and accelerate delivery
- Based in the US, open to 25% domestic travel, and eligible to work in the US without visa sponsorship
Nice to have
- Experience in EdTech, consulting, or fast-paced operating roles
- Familiarity with tools like Linear, Notion, Jira, or custom AI dashboards
- Exposure to vendor scorecards or procurement processes at scale
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.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Accept Job Offer.
Pass 
proctored test.
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