Director Program Management, 2 Hour Learning (Remote) - $200,000/year USD

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 Won’t 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
Director Program Management Key Responsibilities
The execution layer at 2 Hour Learning needs an operator who produces reliable, AI-powered dashboards, scorecards, procurement packages, and contract controls that give executives the clarity and leverage to hold vendors accountable, control costs, and accelerate delivery across a $50M EdTech portfolio.
Basic 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 Requirements
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
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.
Here’s How They’re Fixing It.
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.
Crossover Job Code: LJ-5669-US-Atlanta-DirectorProgra.011

Work arrangement
Yes