Case Study 
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 how customers would react. I pushed for two things: pricing PRO at $149 based on its real value (a 50% pricing increase), and communicating the change early and clearly without apologizing. Customers were given six weeks’ notice, knowing this would increase cancellations but significantly reduce post-renewal refunds.
The result was limited backlash – only roughly 1.5% of customers replied with critical feedback or frustration. More importantly, TEC experienced a 150% increase in renewal revenue and 135% increase in new sales revenue. Refunds dropped, support pressure eased, and pricing finally aligned with 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
Case Study 
STELLARWP
Building an AI-first support experience without breaking customer trust
“I was dead-set against AI support until Matt showed me how his process elevated the role of human agent and prioritized the customer getting to that expert help immediately.”
Ben Meredith
Director of Support, StellarWP
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 our public documentation and monitored performance closely. After reaching roughly 80% resolution from chat interactions, we expanded it into our plugins to create a true AI-first touch experience.
The real shift wasn’t the tool. It was operational. Support responsibilities moved upstream toward documentation quality and chat monitoring, with continuous feedback loops to improve both. AI became effective because the system around it was designed to support it.
Case Study 
GiveWP
Respecting Intent instead of Optimizing Around it.
Email open and click rates were declining, even as the list continued to grow. What first appeared to be an email performance issue led to a full funnel audit, from signup promises to ongoing content delivery.
That audit surfaced the real problem: expectations weren’t being met. We were making content promises in different ways but always only giving fundraising tips. Rather than optimizing individual emails, we added a new email cadence. Mondays were Product Updates, Wednesdays were Fundraising Tips.
Engagement improved, opens and clicks increased, and new incoming subscribers stayed longer. The improvement came from aligning content with intent and delivering on what was promised..
“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
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