Building context into everything: A conversation with Dennis, CEO

Brandon Waselnuk

January 30, 2026

I sat down with Dennis Pilarinos, founder and CEO of Unblocked, to talk about why he started the company and where he sees developer tools going. We covered everything from why they almost named the company "Bother," what happens when the CEO feels too embarrassed to ask his own team a question, to why the best engineers he's worked with only speak up when it matters.

Here's an overview of our conversation.

"This fucking sucks"

Dennis has been building developer platforms for two decades. He was at Microsoft when Azure was a single machine plugged into a direct internet connection in his office—back when Amazon was still "the ‘bookseller’" that had just launched S3 and EC2 as beta services. He started AWS's Vancouver office as employee number one. He built Buddybuild, a mobile CI platform that Apple acquired three years after founding.

Through all of it, he kept running into the same problem.

"I was like, this fucking sucks. And I don't want to have to do it this way. There's gotta be a better way."

The problem was context. At Apple, his peers had been there for 23 years minimum. He was the new guy who didn't know why decisions had been made, how things worked, or any of the tribal knowledge that made everyone else effective. At Buddybuild, he watched smart people join the team and struggle for weeks because they didn't have the background they needed.

So he started Unblocked.

What "context" actually means

I asked Dennis to define context, since it's become one of those words that means everything and nothing.

"Context to me is all the information you need to be good at your job."

He described it as tribal knowledge—the stuff in people's heads, in old Slack threads, in decisions made six months ago that nobody documented. The information that separates the engineer who's spinning their wheels from the one who's actually shipping.

Then he gave me a thought experiment. Imagine hiring a sharp new engineer, high intellectual horsepower, very eager. Now ask them to implement a feature or fix a bug, but they can only look at the source code. Nothing else. No Slack, no Jira, no docs, no asking anyone questions.

That's how Dennis thinks about most AI coding tools. Their genesis was code generation, so the only context they have is source code. Which is setting them up to fail.

They almost called it "Bother"

Here's a story most people don't know. When they were naming the company, Dennis was driving down 280 in San Francisco with one of their investors, bouncing around ideas.

They landed on "Bother." As in: you don't bother me, I don't bother you.

"The domain would've been usebother.com. I think I might still own it."

The namespace might still be in the codebase somewhere. But the idea stuck: you shouldn't have to bother your coworkers—or wait for them to bother you—to get the information you need. And you definitely don’t want your agents to wait to get the information they need.

Why making questions private changed everything

Unblocked started as a Q&A platform. The philosophy was that there's no such thing as a dumb question, so by default, questions were visible to coworkers. People could learn from each other.

Every once in a while someone would reach out asking to make their question private. No problem—there's a little icon, click it, now it's just between you and Unblocked.

Over time, they noticed more people asking for that option. So they flipped the default: all questions private by default.

"The number of questions skyrocketed. It was unquestionable—there was this point in time where the graph went up and to the right."

Even in supportive teams, people don't want to look stupid. They need a judgment-free space to ask “obvious” questions.

Dennis admitted he experiences this himself. There's a font licensing mechanism at Unblocked where you have to put an API key in your shell. Every time he gets a new machine or changes his shell, he forgets how it works.

"I would feel awkward asking this question because it's been answered three or four times. I don't want the very talented people that I work with being like, 'This guy runs the company. He’s an idiot.'"

So he asks Unblocked. Gets the answer. Moves on with his day.

"You can be loud or you can be dumb"

When Dennis talked about their approach to AI code review, he used a phrase I hadn't heard before.

"You can be loud or you can be dumb, but you cannot be both."

It's not in the employee handbook, but it's how the company operates. The best reviewers on any team aren't the ones leaving the most comments. They're the ones who speak up when it matters and stay quiet when it doesn't. Dennis called it "almost the anti-Clippy thing."

Sorry, Clippy, I know we’re punching down.

"We would rather say fewer things but have them be bang on accurate and helpful. Because those are the people that we like to work with."

Software should be a personification of how people like to work. Nobody wants to work with someone who yammers on with low-value commentary. So why build software that behaves that way?

Shame-driven development

I asked how the team ended up so focused on user experience. Dennis said it comes from personal frustration with bad software.

"I am a person who's very, very frustrated by terrible software experiences. I think it's a form of craftsmanship and I think it reflects on your professionalism."

He’s intolerant of bad software in general. If it’s something he built, it’s unforgivable.

Then he referenced the poker movie Rounders. “Few players recall big pots they have won, strange as it seems, but every player can remember with remarkable accuracy the outstanding tough beats of his career."

"When people write to us and say that we let them down in some way, that is seared into our consciousness. We place way more weight on that than people saying 'I love this thing.'"

I summed it up: "Shame-driven development."

Dennis laughed. "Feel the shame."

"The S in MCP stands for security"

We talked about MCP and how Unblocked's context engine fits into the ecosystem of AI coding tools. Dennis has been in and around protocol spaces for decades—he can tell you about obscure XML standards that predate most developers' careers.

His take: all protocols solve high-impact problems quickly out of the gate, then inevitably run into hard problems. One of their customers put it perfectly:

"The S in MCP stands for security."

It's a silent S.

The current state of affairs is that MCP interfaces return partial information. Answers to real problems are rarely stored in a single system—they're spread across source code, Slack conversations, pull requests, and docs. And often they contradict each other.

Unblocked builds a knowledge graph that stitches it together and figures out what's actually true. Then it surfaces that to whatever tool the developer is using.

Security from day zero

I asked about privacy and security, half expecting the usual corporate answer.

Dennis pointed to buddybuild. They had cloud infrastructure that pulled down source code, built it, and deployed binaries for companies like Starbucks, Wall Street Journal, and New York Times.

"You could do all sorts of nefarious things if you wanted to. You had to build trust."

That experience shaped how Unblocked was built from day zero. Security and privacy aren't afterthoughts you bolt on—they're nearly impossible to add later.

The result: not a single security review has been an issue. One well-known financial services company told them it was the best security review they'd ever done with a company at Unblocked's stage.

Left and right of code gen

Dennis mentioned a customer call from that morning. The customer's take: "Yeah, yeah. I like code generation. I got it. There's a bunch of tools. It's cool. But what happens left and right of the code gen?"

That's where Unblocked lives, across the SDLC. To the left: helping engineers get the context they need before they write code. To the right: understanding why builds failed, doing root cause analysis, proposing fixes. During code gen: giving accurate context to the tools writing code for developers.

The PR Failure Agent is an example of where things are headed. It watches CI failures, reasons about what went wrong using the context engine, and proposes solutions. You click yes and move on with your day. No more digging through log files.

Dennis sees 2026 as the year they push further into AI-led workflows. Not replacing developers, but handling the grunt work so humans can focus on higher-leverage problems.

"The wow moments are where you are AI-led and human-assisted. When something has gone wrong, the machine notices it, reasons about what to do to fix it, and proposes that solution to you."

Listen to the full conversation

This post covers some of the highlights, but the full conversation goes deeper into Dennis's journey from Microsoft to Apple to building Unblocked, the philosophy behind how they make product decisions, and why he thinks most AI tools are setting developers up to fail.

Give it a listen.

Unblocked is available now. Read our docs or reach out to see it in action on your codebase.