After nearly two decades, Jeff Chandler has been part of WordPress long enough to have seen every cycle: innovation, burnout, rebuilding, and reinvention. Once a journalist chronicling the stories of others, he’s now the fresh pair of eyes founders call when they can’t see their own blind spots.
From Reporter to Product Insider
For most of his career, Jeff Chandler stood on the other side of the fence documenting the wins, controversies, and evolutions of the WordPress community through his work at WP Tavern and later WP Mainline.
That perspective gave him something rare: a panoramic view of how products succeed, stumble, and recover.
But in 2024, Jeff took a step that shifted everything. He joined a company as a marketing generalist and, for the first time, experienced what it was like to shape a product from the inside.
“For the longest time, I was on the outside looking in,” Jeff told me. “Now I was on the inside, getting to use my years of experience to influence a product’s direction.”
That experience unlocked something new: a love for working quietly behind the scenes, helping products become stronger from within.
The Blind Spots That Build Up Over Time
Jeff doesn’t believe founders always need outside help from day one. In his view, perspective becomes more valuable as time passes: when teams are so deep in their own systems that small issues start to pile up unnoticed.
He describes it as “the point where priorities shift, things get punted, and product owners become blind to issues that are staring them in the face.”
That’s when his work begins. His role isn’t to fix the code or rebuild the brand; it is to see what everyone else stopped seeing and to mirror that truth back to the team with clarity and empathy.
Start With the Basics: Can Anyone Find You?
Before Jeff ever opens a product dashboard or plugin, he runs a deceptively simple test: he searches for the product online.
If it doesn’t show up on Google, in the WordPress plugin directory, or even on ChatGPT, that’s his first red flag.
To Jeff, visibility is the first indicator of health. “If I can’t find the product,” he says, “other people can’t either.”
Common Sense Over Cleverness
One of the themes that runs through all of Jeff’s work is restraint. In a world obsessed with being flashy, he believes products win when they prioritize users over novelty.
He approaches every review like a user would — not as a developer, not as a marketer. Just someone trying to solve a problem. That approach, refined over years of writing honest reviews and testing plugins, has become his north star.
“A lot of folks want to get cute or fancy with things when in reality, using common sense is all that’s needed for success,” he says.
It’s that perspective: straightforward, grounded, and sometimes uncomfortably honest, that makes his consulting so valuable.
Direct Feedback, Delivered with Empathy
Jeff’s reputation for candor follows him, but what people often overlook is how carefully it’s balanced with understanding.
He doesn’t pull punches, but he never throws them either.
In private consultations, he tells founders exactly what’s wrong, why it matters, and how to fix it without the ego or performance that public commentary often invites. “A sense of understanding generates compassion,” he says. “That enables me to be direct.”
It’s a rare mix: a consultant who speaks plainly but listens deeply.
The Culture Behind the Code
WordPress is an ecosystem with its own language and expectations. Jeff sees that as something every founder must understand before trying to sell to it.
“From the words that are used, to licensing, to interacting with people,” he explains, “there is a set of ingredients that improves the chances of success.” Those who ignore that, he warns, risk damaging their reputation before their product even has a chance to thrive.
Pulling Founders Back to the Surface
Many of his clients share the same trait: they are too close to their product. Too invested. Too busy grinding to notice when they have lost the view. He helps them step back.
His process mirrors that of a new customer: searching for the product, purchasing, installing, testing support, and logging every friction point along the way. After 30 to 40 hours of investigation, he surfaces what founders often can’t: the user’s actual experience.
The result is a detailed, structured report filled with screenshots, suggestions, and opportunities for improvement. When he finally meets with the team, he gives them what he calls “a bird’s-eye view of what’s working and what’s not.”
The AI Question
When asked what founders should be watching most closely, Jeff didn’t hesitate: artificial intelligence.
But he isn’t impressed by the rush to add AI everywhere.
“There is a shift where everyone is wondering how to shove AI into their product,” he told me. “Not every product needs it.”
His advice? Be intentional or skip it entirely.
Jeff’s work is about alignment: helping product creators reconnect with how their tools are found, experienced, and understood by real users.
You can learn more about Jeff’s work and explore his product consulting services at hirejeffc.me.
