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

You have created dashboards. You have monitored milestones. You have managed vendors. You have identified risks. But your deliverables reached a limit. The final decisions were not yours to make.

2 Hour Learning is developing an AI-driven education platform designed to enable students to accomplish a complete day of learning in two hours. Delivering this platform at scale demands coordination across numerous initiatives, technology partnerships, contractual agreements, and capital allocation decisions. Your role is to ensure the execution infrastructure is dependable enough to support executive decision-making.

You will be accountable for the operational outputs that inform those decisions: portfolio dashboards that surface delays before they escalated, vendor scorecards aligned with actual contract terms, structured bid evaluations that clarify trade-offs, and contract governance that prevents unauthorized expenditure. AI will be integrated into your workflow, enabling you to normalize status updates, identify irregularities, evaluate competing proposals, assess vendor delivery, and verify billing accuracy.

This is not a traditional PMO position centered on meetings, procedural adherence, or refined presentation materials. It is designed for an operator who seeks consequential impact. When a vendor fails to deliver, your analysis should make that unmistakable.

When expenditure deviates from contract terms, your oversight should detect it. When executives face a $5M commitment, your work should provide the assurance they need to decide quickly.

What You Will Be Doing

• Manage portfolio-level dashboards covering 10+ simultaneous initiatives, leveraging AI to normalize status inputs, identify delays, highlight obstacles, and sustain an accurate executive perspective on delivery progress, financial status, and exposure
• Conduct scheduled vendor performance assessments and maintain structured scorecards that integrate delivery outcomes, quality metrics, cost performance, contractual adherence, and subjective evaluation factors
• Oversee competitive procurement processes for technology vendors, including creation of standardized bid requests, side-by-side comparisons, evaluation frameworks, statement of work drafting, and data-supported selection recommendations
• Administer contract and invoice oversight by monitoring rate limits, milestone conditions, acceptance standards, and contract modifications, then confirming invoice accuracy against executed agreements prior to payment authorization
• Apply AI tools on a daily basis to examine portfolio information, flag outliers, identify performance gaps, generate decision-ready materials, and minimize repetitive administrative tasks

What You Won’t Be Doing

• Creating status updates that executives review but do not rely on for making decisions
• Operating a meeting-intensive PMO where process coordination takes precedence over tangible execution outcomes
• Approaching vendor management as relationship stewardship while allowing missed obligations to remain unaddressed
• Delegating contracts, statements of work, invoices, or procurement activities to others because they appear overly commercial or technical in nature
• Treating AI as an infrequent productivity enhancement rather than a fundamental component of your operations

Director Program Management Key Responsibilities

Deliver dependable, AI-enabled dashboards, scorecards, procurement materials, and contractual oversight that equip executives with the transparency and control necessary to enforce vendor accountability, manage expenditure, and drive execution velocity across a $50M EdTech portfolio.

Basic Requirements

• Previously owned a portfolio consisting of 10+ simultaneous initiatives with a minimum of $5M in budgetary accountability, including decision-making authority over budget distribution, vendor appointment, or initiative ranking
• Simultaneously managed 5+ external technology vendors, including SaaS providers, AI/ML platforms, marketing agencies, or engineering firms
• Developed and sustained portfolio-level dashboards that tracked indicators such as delivery status, budget consumption relative to projections, milestone achievement, and critical risks or impediments
• Can reference a specific instance where executive leadership relied on your portfolio reporting to inform a go/no-go decision regarding vendor contract renewal, budget reallocation, or initiative deprioritization
• Personally led competitive technology procurement processes, encompassing structured bid assessment, vendor evaluation, negotiation, and final selection
• Drafted or jointly drafted SOWs that included quantifiable deliverables, milestone-based payments, SLAs, acceptance criteria, or other performance-linked provisions
• Negotiated commercial provisions including pricing structures, penalties, fee ceilings, or termination rights, and enforced these provisions via invoice review or remediation actions
• Excellent written communication capabilities, with proficiency in converting intricate financial and operational information into brief, actionable recommendations for executive consumption
• Capable of rapidly analyzing financial and vendor performance data to propose optimization strategies, budget realignment, or vendor termination
• Available to work during US business hours

Nice-to-have Requirements

• Background using AI-powered dashboards, anomaly detection systems, predictive alerting, or natural-language analysis within portfolio management contexts
• Experience in EdTech, technology sectors, consulting, or comparable settings overseeing complex portfolios of external technology vendors
• Proficiency with portfolio and project delivery platforms such as Linear, Jira, or equivalent 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.

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-Austin-DirectorProgra.008