VP Portfolio Operations, 2 Hour Learning (Remote) - $200,000/year USD

You have created dashboards. Monitored deliverables. Managed vendors. Surfaced risks. But your insights stopped short. The final decisions were never yours to make. 2 Hour Learning is developing an AI-driven education model that enables students to accomplish a full day's academic progress in two hours. Scaling this model depends on the synchronized execution of numerous initiatives, technology partnerships, contractual agreements, and capital allocation decisions. Your role is to ensure the execution layer is reliable enough to enable confident, fast decision-making at the executive level. You will control the operational outputs that inform those decisions: portfolio dashboards that reveal delays before they elevate, vendor scorecards anchored to actual contract terms, procurement comparisons that clarify trade-offs, and contract oversight that blocks unauthorized expenditures. AI will be embedded in your daily operations, enabling you to normalize reporting, identify anomalies, evaluate bids, assess vendor delivery, and audit invoices. This is not a traditional PMO position centered on status meetings, procedural governance, or presentation polish. It is designed for an operator who wants their work to drive real outcomes. When a vendor fails to deliver, your documentation should make it undeniable. When expenditures deviate from contract, your systems should flag it. When executives face a $5M investment decision, your analysis should empower them to move with confidence. What You Will Be Doing Maintain portfolio-level dashboards spanning 10+ simultaneous initiatives, leveraging AI to normalize status updates, identify delays, surface obstacles, and deliver a trusted executive perspective on delivery, budget, and risk Conduct regular vendor performance assessments and maintain rubric-driven scorecards that integrate delivery quality, cost efficiency, contractual compliance, and qualitative performance indicators Oversee competitive procurement for technology vendors, including development of structured bid packages, normalized evaluation criteria, scoring frameworks, SOW creation, and data-driven recommendations Enforce contract and invoice governance by monitoring fee limits, milestone triggers, acceptance terms, and contract amendments, then verifying invoices against approved contractual language before authorizing payment Apply AI tools daily to interpret portfolio data, flag irregularities, highlight underperformance, produce decision-ready summaries, and minimize routine PMO workload What You Won’t Be Doing Creating status updates that executives acknowledge but do not reference when making strategic decisions Operating a meeting-centric PMO where process coordination takes precedence over tangible results Approaching vendor management as relationship stewardship while allowing missed commitments to go unaddressed Delegating contracts, SOWs, invoice reviews, or procurement activities to others because they appear too commercial or technical in nature Treating AI as an occasional efficiency tool rather than a foundational element of your operating model VP Portfolio Operations Key Responsibilities Deliver dependable, AI-enabled dashboards, scorecards, procurement frameworks, and contract controls that equip executives with the visibility and leverage necessary to enforce vendor accountability, manage costs, and accelerate execution across a $50M EdTech portfolio. Basic Requirements Held direct ownership of a portfolio comprising 10+ concurrent initiatives with budget responsibility of at least $5M, including decision authority over budget distribution, vendor selection, or initiative prioritization Simultaneously managed 5+ external technology vendors, including SaaS providers, AI/ML platforms, marketing agencies, or engineering firms Developed and sustained portfolio-level dashboards tracking metrics such as delivery status, budget utilization versus forecast, milestone attainment, and critical risks or impediments Can reference a specific instance where C-suite executives relied on your portfolio analysis to decide on a vendor renewal, budget reallocation, or initiative deprioritization Led competitive technology procurement end-to-end, encompassing structured bid assessment, vendor scoring, negotiation, and final selection Drafted or co-drafted SOWs with defined deliverables, milestone-based payments, SLAs, acceptance criteria, or other performance-linked terms Negotiated commercial provisions including pricing structures, penalty clauses, fee caps, or termination rights, and enforced those provisions via invoice verification or remedial measures Proficient in written communication, with demonstrated ability to distill complex financial and operational information into clear, actionable executive recommendations Capable of analyzing financial and vendor performance data rapidly to recommend optimization, fund reallocation, or vendor termination Available to work US business hours Nice-to-have Requirements Experience deploying AI-powered dashboards, anomaly detection, predictive alerts, or natural-language analysis within portfolio management contexts Background in EdTech, technology, consulting, or similar fields managing intricate portfolios of external technology vendors Working knowledge of portfolio and 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. 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 for more details on this topic. Crossover Job Code: LJ-5669-US-Clevelan-VPPortfolioOpe.001 #J-18808-Ljbffr Crossover