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 initiatives. Built reports. Monitored vendors. Escalated risks. But your outputs didn't drive decisions. Someone else made the calls.
2 Hour Learning is constructing an AI-driven education platform engineered to deliver a full day of student learning progress in two hours. Scaling that platform requires synchronizing dozens of initiatives, technology partnerships, contracts, and capital allocation decisions. Your role is to ensure the execution infrastructure is reliable enough to support executive action.
You will control the operational artifacts that inform those decisions: portfolio-level dashboards that reveal delays before they escalate, vendor scorecards anchored to enforceable contract terms, structured procurement comparisons that clarify trade-offs, and contract governance that blocks unauthorized expenditure. AI will be embedded in your workflow, enabling you to normalize status updates, identify outliers, evaluate competitive bids, assess vendor delivery, and audit invoices.
This is not a traditional PMO position centered on meeting facilitation, process adherence, or presentation formatting. It is designed for an operator who expects their work to drive outcomes. When a vendor fails to deliver, your documentation should make that incontrovertible. When costs exceed contract limits, your controls should flag it. When executives face a $5M allocation decision, your deliverables should enable them to decide with speed and certainty. If that degree of accountability aligns with what you've been seeking, apply.
What you will be doing
- Maintain portfolio-wide dashboards spanning 10+ simultaneous initiatives, leveraging AI to normalize reporting, identify delays, flag dependencies, and preserve an executive-ready view of progress, spend, and risk
- Conduct structured vendor performance assessments and sustain rubric-driven scorecards incorporating delivery quality, cost efficiency, contractual adherence, and subjective performance indicators
- Oversee competitive procurement for technology vendors, including creating structured bid requests, generating normalized evaluations, defining scoring criteria, drafting SOWs, and producing data-backed selection recommendations
- Administer contract and invoice governance by monitoring cost ceilings, delivery milestones, acceptance terms, and contract modifications, then validating invoices against executed agreements before authorizing payment
- Apply AI tools daily to interpret portfolio metrics, flag irregularities, highlight vendor underperformance, generate decision-ready summaries, and minimize repetitive PMO tasks
What you will NOT be doing
- Creating status summaries that executives acknowledge but do not use for decision-making
- Operating a coordination-centric PMO where process adherence outweighs tangible results
- Managing vendor relationships as a diplomatic function while allowing missed obligations to go unaddressed
- Delegating contracts, SOWs, invoice reviews, or procurement tasks to others because the content appears too technical or commercial
- Treating AI as a sporadic efficiency tool rather than a fundamental component of your operational approach
Key responsibilities
Deliver dependable, AI-enhanced dashboards, scorecards, procurement frameworks, and contract governance mechanisms that equip executives with the transparency and leverage to enforce vendor accountability, manage expenditures, and drive execution velocity across a $50M EdTech portfolio.
Candidate requirements
- Previously owned a portfolio comprising 10+ simultaneous initiatives with minimum $5M budget accountability, including decision rights over budget distribution, vendor selection, or initiative prioritization
- Concurrently managed 5+ external technology vendors, such as SaaS platforms, AI/ML service providers, marketing agencies, or engineering contractors
- Developed and sustained portfolio dashboards tracking indicators such as delivery status, budget consumption versus forecast, milestone attainment, and critical risks or impediments
- Can reference a specific instance where executive leadership used your portfolio outputs to inform a go/no-go decision on vendor renewal, budget reallocation, or initiative termination
- Directly managed competitive technology procurement processes, including structured bid analysis, vendor evaluation, negotiation, and final selection
- Drafted or co-drafted SOWs containing quantifiable deliverables, milestone-based payments, SLAs, acceptance conditions, or other outcome-linked provisions
- Negotiated commercial provisions such as pricing structures, penalty clauses, cost caps, or termination rights, and enforced those provisions through invoice audits or corrective measures
- Demonstrated written communication capability, with proficiency in distilling complex financial and operational information into actionable executive recommendations
- Capable of rapidly analyzing financial and vendor performance datasets to propose optimization, reallocation, or vendor termination
- Available to operate during US business hours
Nice to have
- Background using AI-powered dashboards, anomaly detection systems, predictive notifications, or natural-language processing in portfolio oversight
- Experience in EdTech, technology, consulting, or comparable sectors managing intricate portfolios of external technology partnerships
- Proficiency with portfolio and project management platforms such as Linear, Jira, or equivalent tools
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.
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