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

Producing status reports that executives read but never use to make decisions

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

Director Of Vendor Program Management 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

Solid 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

Experienc

📌 Director of Vendor Program Management, 2 Hour Learning (Winnipeg)
🏢 Alpha School
📍 Winnipeg