Crossover
Website:
crossover.com
Company:
https://www.linkedin.com/company/crossover
Seniority: Director
Industries: E-Learning Providers, IT Services and IT Consulting, and Business Consulting and Services
Job details:
You've developed dashboards. Monitored deadlines. Pursued vendors. Identified risks. But your analysis reached a limit. You weren't the decision-maker.
2 Hour Learning is creating an AI-driven education system designed to enable students to accomplish a full day of learning in two hours. Scaling that system demands coordination across numerous initiatives, technology partnerships, agreements, and capital allocation choices. Your role is to ensure the execution infrastructure is dependable enough to support executive action.
You will control the operational outputs that inform those choices: portfolio tracking systems that reveal delays before they escalate, vendor performance metrics linked to actual contractual obligations, structured procurement frameworks that clarify trade-offs, and agreement oversight that blocks unauthorized expenditure. AI will integrate into your routine work, enabling you to normalize reporting, identify irregularities, evaluate proposals, assess vendor delivery, and verify billing.
This is not a traditional PMO position centered on coordination meetings, procedural adherence, or refined presentation materials. It is designed for an operator who expects their contributions to drive outcomes. When a vendor fails to deliver, your documentation should make that unmistakable. When expenditure deviates from agreed terms, your safeguards should flag it. When executives must authorize a $5M commitment, your deliverables should enable them to proceed with certainty. If that level of accountability aligns with what you seek, apply.
What You Will Be Doing
- Control portfolio-wide tracking systems across 10+ simultaneous initiatives, leveraging AI to normalize reporting, identify delays, highlight obstacles, and sustain an authoritative executive perspective on progress, funding, and exposure
- Conduct periodic vendor performance assessments and sustain rubric-driven scorecards integrating delivery outcomes, quality standards, cost efficiency, contractual compliance, and qualitative execution indicators
- Direct competitive procurement for technology vendors, encompassing structured proposal requests, standardized evaluations, assessment frameworks, statement of work creation, and data-supported recommendations
- Oversee agreements and billing by monitoring rate limits, deliverable checkpoints, approval standards, and modifications, then verifying charges against executed contracts prior to payment authorization
- Apply AI routinely to examine portfolio information, flag outliers, reveal substandard performance, produce decision-ready materials, and minimize manual administrative overhead
What You Won’t Be Doing
- Creating progress summaries that executives review but do not leverage for decision-making
- Operating a coordination-focused PMO where process management supersedes tangible execution results
- Approaching vendor oversight as rapport-building while unmet obligations remain unaddressed
- Delegating agreements, statements of work, invoices, or procurement choices to others because they appear overly commercial or technical
- Deploying AI sporadically as a convenience tool rather than embedding it as foundational to your operations
VP Portfolio Operations Key Responsibilities
Deliver dependable, AI-enabled tracking systems, performance scorecards, procurement frameworks, and agreement controls that provide executives with the transparency and authority to enforce vendor accountability, manage expenditure, and expedite execution across a $50M EdTech portfolio.
Basic Requirements
- Personally managed a portfolio of 10+ simultaneous initiatives with minimum $5M budget accountability, including decision rights over budget distribution, vendor choice, or initiative ranking
- Oversaw 5+ external technology vendors concurrently, including SaaS platforms, AI/ML systems, marketing contractors, or development firms
- Developed and sustained portfolio-scale tracking systems covering indicators such as execution status, budget consumption versus projection, checkpoint attainment, and critical risks or constraints
- Can reference an instance where executive leadership relied on your portfolio analysis to decide on vendor contract continuation, budget reallocation, or initiative suspension
- Personally directed competitive technology sourcing, encompassing structured proposal assessment, vendor ranking, negotiation, and final selection
- Drafted or jointly drafted statements of work with quantifiable outputs, staged payments, service standards, approval conditions, or other performance-linked provisions
- Negotiated commercial provisions including pricing structures, penalty clauses, cost ceilings, or termination rights and enforced those provisions via invoice scrutiny or remedial measures
- Excellent written communication capabilities, with proficiency in converting intricate financial and operational information into succinct recommendations suitable for executive action
- Capable of evaluating financial and vendor performance information rapidly enough to propose optimization, redeployment, or vendor termination
- Available to work during US business hours
Nice-to-have Requirements
- Background using AI-powered dashboards, anomaly identification, forward-looking alerts, or natural-language processing in portfolio oversight
- Background in EdTech, technology sectors, consulting, or comparable settings managing multifaceted portfolios of external technology collaborators
- Proficiency with portfolio and project tools including Linear, Jira, or equivalent platforms
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-IN-COUNTRY-VPPortfolioOpe
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