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.
2 Hour Learning is building an AI-powered education model designed to help students achieve a full day of academic progress in just two hours. Making that model work at scale requires dozens of initiatives, technology partners, contracts, and investment decisions to move in sync. Your job is to make the execution layer trustworthy enough for executives to act on it.
You will own the operating outputs behind those decisions: portfolio dashboards that expose slippage before it becomes a surprise, vendor scorecards tied to real contractual commitments, competitive bid packages that make trade-offs clear, and contract controls that prevent unsupported spend. AI will be part of your daily workflow, helping you standardize updates, detect anomalies, compare bids, analyze vendor performance, and validate invoices.
This is not a PMO role built around meetings, process compliance, or polished status decks. It is for an operator who wants their work to have consequences. When a vendor underperforms, your evidence should make that obvious. When spend drifts from the contract, your controls should catch it. When executives need to make a $5M decision, your outputs should give them the confidence to make it fast. If that sounds like the level of ownership you have been looking for, apply.
What you will be doing
- Own portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage, expose blockers, and maintain a trusted executive view of delivery, budget, and risk
- Run recurring vendor performance reviews and maintain rubric-based scorecards that combine delivery, quality, cost, contractual commitments, and qualitative performance signals
- Lead competitive technology-vendor procurement, including structured bid packages, normalized comparisons, scoring rubrics, SOW development, and evidence-backed recommendations
- Govern contracts and invoices by tracking fee caps, milestones, acceptance criteria, and amendments, then validating invoices against signed terms before spend is approved
- Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs, and reduce manual PMO administration
What you will NOT be doing
- Producing status reports that executives read but never use to make decisions
- Running a meeting-heavy PMO where coordination matters more than measurable execution
- Treating vendor management as relationship maintenance while missed commitments go unchallenged
- Passing contracts, SOWs, invoices, or procurement decisions to someone else because they look too commercial or technical
- Using AI as an occasional productivity trick instead of a core part of how you operate
Key responsibilities
Candidate requirements
- Directly owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection, or initiative prioritization
- Managed 5+ external technology vendors at the same time, such as SaaS providers, AI/ML platforms, marketing agencies, or engineering firms
- Built and maintained portfolio-level dashboards covering metrics such as delivery health, budget burn versus forecast, milestone completion, and major risks or blockers
- Can point to a case where C-suite leaders used your portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation, or initiative deprioritization
- Directly led competitive technology procurement, including structured bid evaluation, vendor scoring, negotiation, and selection
- Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs, acceptance criteria, or other performance-based terms
- Negotiated commercial terms such as pricing, penalties, fee caps, or exit clauses and enforced those terms through invoice validation or corrective action
- Strong written communication skills, with the ability to turn complex financial and operational data into concise recommendations executives can act on
- Able to analyze financial and vendor-performance data quickly enough to recommend optimization, reallocation, or vendor elimination
- Able to work US business hours
Nice to have
- Experience using AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis in portfolio management
- Experience in EdTech, technology, consulting, or another environment managing complex portfolios of external technology partners
- Fluency with portfolio and delivery tools such as Linear, Jira, or similar systems
You will be working for
Meet a successful candidate
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.
Pass proctored test.
Accept job offer.
Frequently asked questions
Reviews
Meet some people who've landed similar jobs
School sucks. So we’re fixing it.
The education Olympics
It’s hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game.
Salary without side gigs
Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.
Skills make the grade
Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.
Join America’s largest community of 
AI-first education leaders.
