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

You've built dashboards. Tracked milestones. Chased vendors. Flagged risks. But your reports hit a ceiling. You weren't the one making the calls.

At 2 Hour Learning, that ends. We're building the most efficient, AI-powered learning system in the world—compressing a full school day into two hours without compromising outcomes. Behind that vision sits a $50M portfolio of fast-moving EdTech initiatives. Your work will decide whether those initiatives ship on time, on budget, and at quality.

You'll operate the execution engine that drives vendor performance. Maintain real-time dashboards executives trust. Own vendor scorecards that lead to action. Run structured bid processes and validate every dollar billed. If a vendor misses, you catch it. If an invoice is off, you flag it. Your work doesn't support decisions—it drives them.

This is the job for operators who want ownership, not observation. If you're ready to step into a role where accuracy matters, AI is your copilot, and your work directly shapes which vendors stay, scale, or go, we want to hear from you.

What You Will Be Doing

• Maintain live, AI-powered dashboards across 25+ initiatives—ensuring accuracy, visibility, and timeline enforcement
• Run vendor check-ins, build rubric-based scorecards, and surface insights that drive scope cuts, reallocations, or offboarding
• Assemble dual-bid procurement packages with structured comparisons and clear scopes—supporting vendor selection
• Track contract and invoice integrity—ensuring every dollar aligns to deliverables, caps, and signed documentation
• Use AI daily to detect anomalies, draft reports, chase updates, and power all your outputs
  
  

What You Won’t Be Doing

• Sitting in meetings while initiatives slip quietly behind the scenes
• Delegating AI work to analysts or waiting for others to keep tools up to date
• Letting billing errors or vendor slippage go unflagged
• Producing status updates that inform no decisions and drive no action
• Relying on guesswork or feel—your outputs are evidence-backed and exec-ready
  
  

VP Portfolio Operations Key Responsibilities

Produce the dashboards, scorecards, bid packages, and contract controls that power a $50M execution engine and drive real-time vendor accountability.

Basic Requirements

• Owned execution of a multi-initiative program or portfolio ($5M+ scope), with direct vendor involvement
• Built and maintained dashboards, scorecards, or tracking systems executives relied on—not just internal teams
• Experience running vendor check-ins, drafting bid packages, and supporting contracting cycles
• Working knowledge of contracts, SOWs, and invoices—with ability to catch and flag misalignment
• Strong written communication—your memos lead to decisions, not more meetings
• Daily use of AI tools to automate, analyze, and accelerate delivery
• Based in the US, open to 25% domestic travel, and eligible to work in the US without visa sponsorship
  
  

Nice-to-have Requirements

• Experience in EdTech, consulting, or fast-paced operating roles
• Familiarity with tools like Linear, Notion, Jira, or custom AI dashboards
• Exposure to vendor scorecards or procurement processes at scale
  
  

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-US-Virginia-VPPortfolioOpe1