Case studies
These case studies move past theory. They show how a specific choice simplified the work and unlocked growth. The details are practical: what changed, what I pushed for, and what the team did next.
The Events Calendar: raising prices without eroding trust
The Events Calendar needed new pricing for its PRO version. I was part of the cross-functional team that evaluated how bundling a popular add-on into PRO and raising the price would affect revenue, customers, and support. The change improved the product, but it also eliminated a standalone revenue stream and forced a harder decision about existing customers and renewals.
The real risk was less about the price increase and more about how customers would react. I pushed for two things: pricing PRO at $149 based on its real value (a 50% increase), and communicating the change early and clearly without apologizing. Customers got six weeks’ notice. We knew that would increase cancellations, and that it would cut post-renewal refunds.
The result was limited backlash. About 1.5% of customers replied with critical feedback or frustration. Renewal revenue went up 150%, and new sales revenue went up 135%. Refunds dropped, support pressure eased, and the price finally matched the product’s long-term value.
This pricing decision was a team effort, but Matt played a key role in helping us see the second-order effects clearly. He pushed us to price PRO based on its real value and to communicate the change directly and confidently. That combination reduced refunds, eased support pressure, and ultimately helped both the business and our customers.
Zach Tirrell
General Manager, StellarWP
StellarWP: an AI-first support layer that kept customer trust
We wanted to introduce AI as a first-touch support layer, but only if it actually helped customers. Instead of launching it publicly, we started by using our docs-powered chatbot internally and stress-testing it against real support questions.
Once the chatbot consistently resolved issues accurately, we rolled it out on the public documentation and watched it closely. After it reached roughly 80% resolution from chat, we expanded it into the plugins so the first touch could be AI.
The real shift wasn’t the tool. It was operational. Support work moved upstream, toward documentation quality and chat monitoring, with a feedback loop to improve both. AI worked because the system around it was built to support it.
I was dead-set against AI support until Matt showed me how his process elevated the role of the human agent and got the customer to that expert help immediately.
Ben Meredith
Director of Support, StellarWP
GiveWP: respect intent instead of optimizing around it
Email open and click rates were declining, even as the list kept growing. What looked like an email performance problem turned into a full funnel audit, from the signup promise to what people actually received.
The audit showed the real problem: expectations weren’t being met. We were making content promises in different ways, and then only sending fundraising tips. Rather than optimizing individual emails, we added a second cadence. Mondays were product updates. Wednesdays were fundraising tips.
Engagement improved. Opens and clicks went up, and new subscribers stayed longer. That came from lining the content up with what people had signed up for, and then delivering it.
Stepping back to audit the entire funnel made the difference. Once expectations were clear and each stream had a purpose, engagement followed naturally.
Taylor Waldon
Marketing Lead, GiveWP