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

- Generated: 2026-09-21 08:02:50 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4466819102/
- Provider: LinkedIn
- Posted: approximately 2026-09-21 07:02 AM EDT (from '1 hour ago')
- Elapsed since posting: represented by the provider's relative posting label and approximate Eastern timestamp when available
- Applicants: Be among the first 25 applicants
- Work model/location: Remote-friendly; U.S. business hours; independent-contractor agreement
- Compensation: $200,000/year equivalent at $100/hour, 40 hours/week, 50 weeks/year
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 61%

## Direct-match strengths

AI-enabled portfolio reporting, executive dashboards, budgets, prioritization, vendors, contracts, operational metrics, and decision support.

## Hard or material gaps

Hard function/scope gaps: the role requires direct ownership of 10+ concurrent initiatives with at least $5M budget authority, five or more simultaneous vendors, competitive procurement, SOW authorship, commercial-term negotiation, fee-cap and invoice enforcement, and a documented C-suite go/no-go decision based on portfolio data. Those exact procurement and contract-control depths are not supported.

## Evidence map

1. Own 10+ initiatives and $5M+ budget allocation (weight 3, evidence 1/3) — Portfolio and budget ownership are direct, but the exact scale and allocation authority are unsupported.
2. Manage 5+ external vendors simultaneously (weight 3, evidence 1/3) — Vendor management is direct; the required simultaneous scale is not documented.
3. Portfolio dashboards and risk visibility (weight 3, evidence 3/3) — Direct KPI, portfolio, delivery, and executive reporting.
4. C-suite go/no-go decisions from portfolio data (weight 3, evidence 1/3) — Executive advisory is direct; the exact required example is not documented.
5. Competitive procurement and vendor scoring (weight 3, evidence 1/3) — Build-versus-buy and vendor decisions are direct; formal bid-package ownership is not.
6. SOW and commercial-term negotiation (weight 3, evidence 0/3) — Specific pricing, penalties, fee caps, and exit-clause negotiation are unsupported.
7. Invoice validation and contract enforcement (weight 3, evidence 0/3) — Not source-supported.
8. AI-enabled operations (weight 2, evidence 3/3) — Direct AI workflow automation and analytics.
9. Compensation eligibility (weight 2, evidence 3/3) — Exactly $200,000 annual equivalent qualifies.

## Keyword diagnostic

AI-enabled portfolio and executive-decision strengths do not overcome mandatory procurement, commercial negotiation, invoice-control, and portfolio-scale evidence gaps.

## Full normalized job description

You’ve built dashboards. Tracked milestones. Chased vendors. Flagged risks. But your reports hit a ceiling. You weren’t the one making the calls.
2 Hour Learning is building an AI-powered education model designed to help students achieve a full day of academic progress in just two hours. Making that model work at scale requires dozens of initiatives, technology partners, contracts, and investment decisions to move in sync. Your job is to make the execution layer trustworthy enough for executives to act on it.
You will own the operating outputs behind those decisions: portfolio dashboards that expose slippage before it becomes a surprise, vendor scorecards tied to real contractual commitments, competitive bid packages that make trade-offs clear, and contract controls that prevent unsupported spend. AI will be part of your daily workflow, helping you standardize updates, detect anomalies, compare bids, analyze vendor performance, and validate invoices.
This is not a PMO role built around meetings, process compliance, or polished status decks. It is for an operator who wants their work to have consequences. When a vendor underperforms, your evidence should make that obvious. When spend drifts from the contract, your controls should catch it. When executives need to make a $5M decision, your outputs should give them the confidence to make it fast. If that sounds like the level of ownership you have been looking for, apply.
What You Will Be Doing
Own portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage, expose blockers, and maintain a trusted executive view of delivery, budget, and risk
Run recurring vendor performance reviews and maintain rubric-based scorecards that combine delivery, quality, cost, contractual commitments, and qualitative performance signals
Lead competitive technology-vendor procurement, including structured bid packages, normalized comparisons, scoring rubrics, SOW development, and evidence-backed recommendations
Govern contracts and invoices by tracking fee caps, milestones, acceptance criteria, and amendments, then validating invoices against signed terms before spend is approved
Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs, and reduce manual PMO administration
What You Won’t Be Doing
Letting status reports sit unread rather than driving decisions that executives can act on
Running a meeting-heavy PMO where coordination matters more than measurable execution
Treating vendor management as relationship maintenance while missed commitments go unchallenged
Passing contracts, SOWs, invoices, or procurement decisions to someone else because they look too commercial or technical
Using AI as an occasional productivity trick instead of a core part of how you operate
VP Portfolio Operations Key Responsibilities
Produce reliable, AI-powered dashboards, scorecards, procurement packages, and contract controls that give executives the clarity and leverage to hold vendors accountable, control costs, and accelerate delivery across a $50M EdTech portfolio.
Basic Requirements
Directly owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection, or initiative prioritization
Managed 5+ external technology vendors at the same time, such as SaaS providers, AI/ML platforms, marketing agencies, or engineering firms
Built and maintained portfolio-level dashboards covering metrics such as delivery health, budget burn versus forecast, milestone completion, and major risks or blockers
Can point to a case where C-suite leaders used your portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation, or initiative deprioritization
Directly led competitive technology procurement, including structured bid evaluation, vendor scoring, negotiation, and selection
Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs, acceptance criteria, or other performance-based terms
Negotiated commercial terms such as pricing, penalties, fee caps, or exit clauses and enforced those terms through invoice validation or corrective action
Strong written communication skills, with the ability to turn complex financial and operational data into concise recommendations executives can act on
Able to analyze financial and vendor-performance data quickly enough to recommend optimization, reallocation, or vendor elimination
Able to work US business hours
Nice-to-have Requirements
Experience using AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis in portfolio management
Experience in EdTech, technology, consulting, or another environment managing complex portfolios of external technology partners
Fluency with portfolio and delivery tools such as Linear, Jira, or similar 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. 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-Clevelan-VPPortfolioOpe.005

## Artifact metadata

- Resume: Not generated because the fit gate returned FAIL.
- Cover letter: Not generated because the fit gate returned FAIL.
- LinkedIn note: Not generated for a FAIL role.
- Google Drive used: No