Weekly Special - IT Procurement Was Supposed to Get Easier. It Didn’t

We were promised flexibility. What we got was a commercial obstacle course with every vendor holding a new map. Sounds familiar?

Nowadays, IT Procurement is about surviving the licensing gymnastics, the vendor bait-and-switch, and the 5-alarm fire that someone politely calls “renewal.”

I wish this was theory. I’ve seen this repeated across five industries over time.

And I’ve packaged it into tools because duct tape alone no longer cuts it.

1. We Thought We Were Buying. Turns Out We’re Just Renting Trouble.

There was a time when procurement was simple: perpetual license, capex budget, done.
Now?

I’m renting access to software I don’t own, via metrics I honestly do not understand, in environments no one fully controls — and somehow I still get blamed for the overage.

Remember Broadcom’s VMware pivot? That wasn’t just about subscriptions.
It was a full-frontal assault on predictability.

The old rules died quietly.
What’s scary is how many procurement teams are still playing by them.

2. Licensing Models Aren’t Just Confusing — They’re Weapons

There’s nothing neutral about licensing anymore. The model is the margin strategy. 

Let’s skip the jargon and call it like it is.

• Per-User? We’ll pay for ghost accounts nobody uses.

• Per-Core? We’re billed for potential power, not actual output.

• Consumption-Based? Finance roulette. Guess wrong and we’re toast.

• BYOL? Sounds dreamy… until Oracle kicks in our door for an audit.

Licensing metrics are often pitched as flexible, but they’re engineered for opacity.

The more dynamic the environment (think: Kubernetes, hybrid cloud, LLM pipelines), the harder it is to pin down what we’re paying for — and why.

👉 Want the full breakdown? I made a cheat sheet that slices through every licensing model, including real traps and audit risks. 

Download the Licensing Models Cheat Sheet

3. Renewals Aren’t a Stage. They’re a Trap

Renewals looked easy. We’ve already deployed. The team’s trained. The clock is ticking. 

That’s exactly what the vendor is counting on. 

By the time we are looped in — usually with less than 60 days to go — the damage is already done: 

• The SKU is “retired” 

• The new “bundle” includes features no one asked for 

• The cost? Up 30%, and “aligned with market value” 

Renewals are the most expensive part of the IT procurement cycle — not because the pricing is higher, but because our leverage is lower. 

We need to: 

• Start prep at least 3–6 months out (even 12 for more complex renewals)

• Audit actual usage (not just invoices) 

• Benchmark externally (and use vendors’ own fiscal calendar against them) 

• Identify bluff levers — including competitors, partial exits, and feature parity workarounds 

👉 I put it all into a Renewal Prep Checklist — already saved six figures for one client. It’ll save your sanity, too

Grab the Renewal Prep Checklist

4. Usage-Based Pricing: The Nicest Way To Rob Us Blind

Usage-based pricing was sold as fair. It was also sold as transparent. How does it really seem for you? 

In reality, most organizations can’t forecast usage past next quarter, let alone next year. AI pipelines and cloud workloads scale fast — and quietly. Until Finance calls asking why the Snowflake bill doubled... again. 

Meanwhile, vendors bury “value metrics” in vague definitions: tokens, inference minutes, API calls, etc. They then auto-scale them. We only realize what hit us after the invoice. 

Here’s the brutal truth: every vendor has already planned how they’ll upsell us.

Our job isn’t to avoid that — it’s to control when and how it happens. 

That means: 

• Capping usage and auto-alerting thresholds 

• Demanding rate freezes (yes, even in cloud deals) 

• Requiring transparency into “reserved” vs “actual” consumption 

• Setting formal intake governance for AI pilot expansions 

Need help framing this pushback? 

👉 I built a negotiation slide deck: How to Challenge Licensing Models — includes 10 vendor playbook scenarios, 7 tactical counters, and commercial clause examples you can drop into MSAs. 

Download the Negotiation Slide Kit

5. The Real Problem Isn’t the Vendor. It’s Our Own Visibility 

Let’s get honest. Most companies are bad at managing what they already bought. 

Entitlements are buried in contracts. Business units don’t track what they use. Finance only sees the PO. IT knows uptime, not usage.

And procurement? We’re supposed to negotiate in the dark with all of it. 

The worst part? Vendors know this. That’s why they push for bundles, shift SKUs, and act surprised when we question their 20% uplift. 

We needs to stop walking into renewal without: 

• Usage per module / seat / region 

• A single view of entitlements by vendor 

• Named business owners per product 

…so that we’re not negotiating with a blindfold. 

👉 In the IT Procurement Vault, I’m releasing tools to help map this chaos. But even a shared Google Sheet with consistent columns can outperform 90% of enterprise tracking. 

6. Infrastructure and SaaS Need Two Different Toolkits 

Still treating Red Hat like Salesforce? Or Snowflake like Dell? That’s how we get burned. 

SaaS deals bleed slowly — per user, per module, creeping overages. 
Infrastructure deals hit hard — support uplifts, sudden re-buys, version obsolescence. 

Our procurement tactics need to reflect that. 

For SaaS: 

• Monitor license creep quarterly 

• Fight for downgrade rights mid-term 

• Track true usage across modules 

For Infrastructure: 

• Break out BOMs (watch for “free” line items that cost big later) 

• Freeze support costs upfront 

• Plan for lifecycle — and flag model retirements in Year 2 

The mistake is using a “software is software” mindset when the commercial levers are completely different. 

7. The Future? More Traps. Let’s Plan for Them. 

Want to know what’s coming? 

• Vendors will change licensing models mid-contract (again) 

• ESG compliance and AI audit clauses will show up in our RFPs 

• Evergreen clauses will trap our worst deals indefinitely 

• Our biggest vendors will absorb others — and force SKU “harmonization” 

The only way out? Contracts that include: 

• Exit clauses for licensing metric changes 

• Portability rights (especially for cloud or AI workloads) 

• Renegotiation triggers on ESG/regulatory shifts 

• Visibility thresholds (where if the vendor doesn’t provide reports, we stop paying) 

The playbook is no longer about savings. 

It’s about structural flexibility — the ability to walk, shift, or bluff when needed. 

Let’s Wrap This With the Only Thing That Matters: Control

Every toolkit in the Vault exists because I’ve been burned, blindsided, or boxed in.

This isn’t theory. It’s triage.

And I’m tired of seeing procurement treated like the “paperwork” team when it’s the only function standing between a bad deal and a budget disaster. 

Here’s where to start:

• Licensing Types Cheat Sheet — so you stop getting gaslit by made-up metrics 
  👉 Get it 

• Renewal Prep Checklist — so your next renewal doesn’t become a panic event 
  👉 Get it 

• How to Challenge Licensing Models (Slides) — for stakeholder training and internal alignment 
  👉 Get it 

• IT Procurement Vault, everything in one plus the IT Procurement Playbook. The master guide to modern IT buying.
  Covers licensing traps, SaaS vs infra tactics, AI/cloud risk governance, renewal strategies, and commercial red flags.

  👉 Get it 

 Want regular war stories, vendor strategies, and tools that actually work? 

📬 Subscribe to “The Weekly Pull” — No fluff. Just firepower. 

And next time someone says “It’s just a renewal” — send them this article.

Or better, forward the checklist and ask if they want to gamble six figures on being unprepared. 

Stay nerdy,

Zvi