Every marketing operations pro has a few ghosts in their past — the projects that still send a chill down your spine.

In the spirit of Halloween, CI Managing Partner Mike Shaw pulled out some of the scariest tales from the world of marketing operations. They’re funny now, but at the time? Truly horrifying.

Below are four real stories that remind us why smarter systems, automation, and AI-driven workflows aren’t just “nice to have” — they’re survival tools.

1. The $10,000 Ad Resize

Picture this: a life sciences brand, a massive agency budget, and a simple creative request.
All they needed was to resize a leaderboard ad — from 728x90 to 970x250. The cost? $10,000.

Yes, you read that right.

The agency justified it by saying they needed to re-enter the MLR (Medical, Legal, Regulatory) process — again. Never mind that the content was already approved. The image was just being resized.

It’s a story many pharma marketers can relate to: paying premium prices for basic tasks because of process bottlenecks and outdated approval chains.

The fix:
Modern marketing teams are adopting modular content databases — systems that store approved assets, claims, and layouts as reusable components. Resize an ad, update a copy block, or change a background — all without starting from scratch.

2. The Screenshot Nightmare

Another brand was using Salesforce Experience Cloud for patient portals and Veeva Vault for MLR approvals — a powerful combination in theory.
In practice, every update required someone to take hundreds of screenshots of every button, page, and line of copy… and upload them one by one for review.

Each upload took three to four days.

The team called it “the process.” Mike called it what it really was: a time-sucking monster from 2005.

The fix:
Automated audit and submission tools now allow integrated systems to pass content directly between platforms. No screenshots. No manual uploads. Just traceable, compliant data flowing through one connected workflow.

3. The Three-Word Compliance War

A crypto exchange wanted to run a bold new campaign with a simple message:
“Bitcoin is money.”

Seems harmless — until compliance teams across global markets got involved.
In some countries, that phrase was fine. In others, it was a potential legal violation. What followed was weeks of executive-level debate over those three words.

The fix:
Global brands need compliance-aware systems that automatically adapt campaigns by geography.
A platform that recognizes regional disclosure rules could have prevented weeks of chaos — and allowed the U.S. team to run its campaign safely without regulatory risk elsewhere.

4. The Regulatory Audit From Hell

Just before the holidays, a regulator requested a full audit:
Every marketing campaign run that year, every ticket, every approval record, every published version — for one specific region.

The team spent weeks digging through Jira, drives, and email chains to match what was approved versus what actually went live. Holiday plans? Cancelled.

The fix:
When marketing operations live across disconnected systems, audits become nightmares.
With integrated workflow tools and agentic AI platforms, teams can automatically track approvals, pull records, and produce audit-ready evidence in minutes.

How to Banish the Nightmares for Good

Mike’s key takeaway: every one of these horror stories could have been prevented with three foundational upgrades:

1. An Integrated Workflow Tool
   Connect every stage of content creation, review, and publishing across your tech stack.
   One source of truth, one continuous audit trail.
2. A Modular Content Database
   Store approved content blocks and claims like LEGO pieces — reusable, compliant, and traceable.
3. An Agentic AI Platform
   Offload manual work to intelligent systems that route, check, and prepare content automatically — freeing your team to focus on strategy, not screenshots.

Final Thought

Marketing operations shouldn’t feel like a haunted house of disjointed systems and sleepless nights.
With the right structure, automation, and AI, you can turn every horror story into a playbook for smarter, faster, and compliant marketing.

So — what’s your biggest marketing ops nightmare?

About the Author
Mike Shaw is Managing Partner at CI, where he helps global brands modernize their content supply chains and marketing operations through AI and automation.