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Brandon Penn
Brandon Penn is the Chief Marketing Officer at Parabola. Before joining, he led marketing at Shopify Logistics (acquired by Flexport) and Runway.
Last updated:
October 3, 2025

Stress Test Your Peak Plan: Operational Readiness for the Holiday Surge

This blog post is based on my recent conversation with Tyler Scriven and Faith McCoy Scriven at Saltbox's Virtual Conference. You can view the recording here.

Every year, the same story plays out: brands coast into October feeling confident, then watch their operations buckle under the weight of Black Friday and Cyber Monday. Orders flood in. Systems that hummed along in July suddenly grind to a halt. Manual processes that worked fine at 100 orders a day collapse at 1,000.

The difference between brands that thrive during peak season and those that merely survive isn't budget or headcount. It's preparation. The best operators treat Q4 like a marathon runner treats race day: they train past the conditions they expect, stress-test every system, and build flexibility into their operations before the starting gun fires.

We sat down with operations leaders at brands like On Running, Faherty, and Skims to understand what actually breaks first, how to prevent it, and how to turn the holiday surge into a catalyst for long-term operational excellence. Here's what we learned.

What breaks first (and how to prevent it)

The first cracks almost always appear in data flow between systems. When order volumes spike, any weak link in the data chain can snowball quickly. A slightly off-format file from a 3PL, a carrier delay that isn't flagged fast enough, or a single mis-keyed SKU triggers a chain reaction: wrong labels, late shipments, angry customers.

For smaller teams without a 3PL, the same risk lives in the handoffs between Shopify, shipping software, and the packing station. If you're still relying on manual spreadsheet uploads or someone double-checking inventory counts, those steps simply don't scale.

Think of it like training for a marathon. Runners don't just run 26.2 miles once and call it good—they build endurance and train past race conditions so the big day feels manageable. Your operations should work the same way: push your systems beyond the peak you expect. Run larger test volumes, feed in messy data, and make sure every connection holds up so the first surprise doesn't expose a weak spot.

The smartest operators stress-test their handoffs early (returns processing, order routing, carrier reconciliation) so they know their systems can handle five or ten times the normal load. Don't wait until November to discover your breaking points.

Data as infrastructure, not an afterthought

Treating data as core infrastructure changes everything. In practice, that means every system—your storefront, ERP, shipping tools—feeds accurate, real-time information into one clean flow.

The most prepared brands set up automated workflows that pull and transform data as it changes, creating a single source of truth for orders, inventory, and service levels. When volumes spike, they're not digging through yesterday's spreadsheets. They're making decisions based on live numbers they trust.

Being able to act on data starts with the hygiene of that data. Clean data flowing automatically between systems means fewer downstream errors and better customer experiences when the stakes are highest. The holiday surge exposes every crack in disconnected systems: Shopify, 3PLs, carriers, ERPs. Parabola acts as connective tissue, making sure data flows cleanly across tools so those cracks don't become chasms.

Where to start with AI: Find your time drains

When we talk to operators about AI, the most common question is: "Where do I even start?" The answer is simpler than you might think: look for the manual, tedious work that's eating up your time.

Ask yourself: What am I doing repeatedly that makes me think, "There has to be a better way"? Where am I copying and pasting data between systems? What tasks spike during busy periods and turn into bottlenecks?

A great starting point is something simple but powerful: use AI to extract or parse data from PDFs. Set up a workflow that reads a shipment PDF and outputs a clean table in the same format every time. It's a low-lift way to turn messy documents into structured data you can actually use.

From there, operators get more ambitious. We've seen customers build AI-driven workflows for tariff scenario modeling, invoice reconciliation, and exception summarization. These are back-office processes where AI quietly saves time and money, even if they aren't flashy.

Here's the reality check: MIT's Media Lab found that **95% of AI pilot projects fail to deliver measurable financial impact.** Not because the technology doesn't work, but because leaders don't embed AI where it can create real value. Too often, companies run marketing experiments while ignoring the operational tasks where the biggest savings live.

There are countless AI products out there, and depending on what you're looking to do, Parabola can be a great start. We've published templates of our top AI workflows (the same ones used by On Running, Faherty, and Skims) so even a team of fewer than ten people can drop them in and start automating right away.

The key is experimentation. Start small, prove the value in a single workflow, and build from there. By the time peak hits, those workflows are trained and reliable, not experimental.

Build for flexibility: Your Q4 contingency plan

Peak season always throws a curveball: carrier delays, a SKU that sells out, or a promo that blows up bigger than you planned. You can't predict every twist, but you can design your operations so you can pivot fast.

A simple example: maintain a single source of truth for orders and inventory (even a well-structured Google Sheet works). Then set clear decision rules: backup carriers, adjustable cut-off times, a short "if X happens, do Y" checklist. When something pops up, you're not scrambling.

Parabola gives teams the ability to adapt workflows quickly, without needing to wait on engineering. That agility lets you redirect orders, change rules, or spin up new reports mid-season when surprises hit. The goal is to spot issues early and pivot quickly, so you're never stuck while customers are waiting on you.

Lessons beyond Q4: Turn peak into long-term advantage

Treat the holiday rush as a free stress test for your entire operation. Every bottleneck you spot is a chance to automate and improve for the long term. Document what broke, capture the fixes, and turn those into standard workflows so they pay off in Q1 and beyond.

Experiment with AI now, not later. Over the past year we've seen engineering teams adopt AI quickly; the next wave will be operations and supply-chain teams—the people spending hours moving data around in spreadsheets. Tools for parsing and cleaning data can take a lot of that manual work off your plate.

If you use the lessons from this peak season to test and refine those workflows, you'll start the new year with systems that are faster, cleaner, and ready to scale. The pressure test of holiday surge often exposes where systems are weakest. Brands that document and automate fixes carry those efficiencies forward. Holiday season becomes not just survival, but a catalyst for operational maturity.


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Ready to stress-test your operations before the surge hits? Explore our library of pre-built workflows and AI templates used by leading brands, or join our community of operators sharing peak season strategies.

Brandon Penn
Last updated:
October 3, 2025
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