Director of Program Operations $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 tracked timelines. Built status reports. Monitored vendors. Surfaced risks. But your analysis never crossed the line into real authority. You informed decisions—you didn't shape them.
2 Hour Learning is developing an AI-driven education platform engineered to deliver a complete day of learning progress in two hours. Scaling that platform demands coordination across dozens of workstreams, technology partnerships, procurement cycles, and capital allocation choices. Your role is to build an execution infrastructure reliable enough that leadership can depend on it for high-stakes decisions.
You will deliver the operational intelligence that supports those choices: portfolio command centers that surface delays before they escalate, vendor performance records anchored to contractual obligations, procurement frameworks that clarify trade-offs, and financial controls that eliminate unauthorized expenditure. AI will be embedded in your daily operations—standardizing status collection, flagging irregularities, evaluating bid responses, assessing supplier performance, and auditing invoices.
This is not a traditional PMO position centered on governance, meetings, or presentation polish. It is designed for someone who wants their outputs to drive action. When a vendor fails to deliver, your data should make the case unmistakable. When costs exceed contract terms, your controls should intercept it. When leadership faces a $5M commitment, your analysis should enable them to decide with speed and confidence. If that describes the level of impact you've been pursuing, we encourage you to apply.
What you will be doing
- Build and maintain portfolio-level command centers spanning 10+ parallel initiatives, leveraging AI to normalize reporting, identify delays, flag obstacles, and sustain an authoritative executive perspective on delivery status, budget utilization, and risk exposure
- Conduct structured vendor performance assessments and manage scoring frameworks that integrate delivery timeliness, output quality, cost efficiency, adherence to contract terms, and qualitative execution signals
- Direct competitive procurement for technology vendors, encompassing structured RFP packages, apples-to-apples bid analysis, evaluation rubrics, statement-of-work creation, and evidence-supported vendor recommendations
- Administer contract compliance and invoice oversight by monitoring rate limits, deliverable milestones, acceptance standards, and contract modifications, then auditing invoices against executed agreements before authorizing payment
- Integrate AI into everyday workflows to parse portfolio metrics, identify outliers, highlight underperformance, produce decision-grade summaries, and eliminate repetitive administrative overhead
What you will NOT be doing
- Creating progress updates that executives acknowledge but never reference when making decisions
- Operating a process-heavy PMO in which stakeholder alignment supersedes tangible delivery outcomes
- Approaching vendor oversight as relationship stewardship while allowing missed obligations to go unaddressed
- Delegating contracts, statements of work, invoice reviews, or procurement judgments because they appear overly technical or commercial
- Treating AI as an occasional efficiency enhancement rather than a foundational element of your operating model
Key responsibilities
Deliver dependable, AI-enhanced dashboards, vendor scorecards, procurement frameworks, and contract governance mechanisms that equip executives with the visibility and authority to enforce vendor accountability, manage expenditures, and drive execution velocity across a $50M EdTech investment portfolio.
Candidate requirements
- Previously managed a portfolio of 10+ simultaneous initiatives with a minimum of $5M in budget accountability, including decision rights over budget distribution, vendor selection, or initiative ranking
- Oversaw 5+ external technology suppliers concurrently, such as SaaS vendors, AI/ML service providers, marketing contractors, or software development firms
- Designed and operated portfolio-level command centers tracking indicators like delivery health, budget consumption versus plan, milestone attainment, and critical risks or impediments
- Can cite a specific instance where executive leadership relied on your portfolio insights to authorize or halt a vendor contract renewal, budget reallocation, or initiative suspension
- Personally directed competitive technology sourcing processes, including organized bid assessment, supplier scoring, commercial negotiation, and final vendor selection
- Drafted or jointly developed statements of work featuring quantifiable deliverables, phased payment structures, service-level agreements, acceptance thresholds, or other performance-linked provisions
- Negotiated commercial provisions including pricing structures, penalty clauses, spending limits, or termination rights, and upheld those provisions through invoice audits or corrective measures
- Exceptional written communication capabilities, with demonstrated ability to distill complex financial and operational information into succinct, actionable executive recommendations
- Capable of rapidly analyzing financial and vendor data to propose optimization strategies, resource shifts, or vendor termination
- Available to work during US business hours
Nice to have
- Background using AI-powered dashboards, anomaly flagging, predictive alerting, or natural-language processing within portfolio oversight functions
- Prior work in EdTech, technology sectors, consulting, or comparable settings overseeing multifaceted portfolios of external technology suppliers
- Proficiency with portfolio and project management platforms such as Linear, Jira, or equivalent systems
Applying for a role? Here’s what to expect.
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