From the Founder | How General Assembly Became an AI Skills Leader by Listening to Inbound

Why Work Here is a series in which Amit Matani, CEO of Wellfound, has honest, behind-the-scenes conversations with founders, executives, and employees about why their companies are worth joining.

When Daniele Grassi joined General Assembly in 2020, the company was doing what most coding bootcamps do: teaching people to become software developers. The customer base was predictable—tech companies, career-switchers, people trying to break into the industry.

Then ChatGPT launched in late 2022, and the requests started coming from places Grassi hadn't expected. A European government asked about AI training for civil servants. Healthcare systems wanted to understand how AI could improve patient outcomes. Hospitality chains were trying to figure out how to use these tools in their operations.

"We're getting a ton of inbound from different sectors—hospitality, health care, government, organizations you wouldn't typically think of as our customers," Grassi says.

The pattern was clear. General Assembly's market had shifted from people who wanted to become developers to basically every organization trying to understand what AI means for their workforce.

Grassi, now President and CEO, recently sat down with Amit Matani, CEO of Wellfound, to discuss what that shift has meant for the company. Their conversation covers how to recognize when disruption is expanding your market rather than distracting you, what kind of people thrive during that kind of change, and how to stay focused when opportunity appears in every direction.

🎥 Watch the full interview on YouTube | Listen on Spotify

When the Market Redefines Itself

General Assembly had spent years building a reputation in a specific niche. They knew how to take someone with little coding experience and turn them into a hireable developer. The model worked. But when AI exploded into the mainstream, that expertise suddenly mattered to a much broader audience.

"When ChatGPT came out, everything started to tip. The demand for AI skills went from zero to a hundred. And it wasn't just developers who wanted to learn—it was everyone."

Market shifts are easy to spot in retrospect. Recognizing them while they're happening is harder, especially when the signal comes from customers you never planned to serve. For Grassi, the inbound from governments and non-tech industries wasn't noise to filter out. It was information about where the market was headed.

"We realized our total addressable market had shifted from a niche—people who wanted to become developers—to literally everyone. That's not something you plan for. That's something you recognize and respond to."

General Assembly made a decision: AI skills training wasn't an adjacent product line. It was their new core business. They started building curricula for prompt engineering, AI governance, strategic implementation. They developed programs for everyone from individual contributors to C-suite executives trying to understand how this technology would reshape their organizations.

"We had to evolve very quickly. The skillsets people needed were changing faster than we'd ever seen. And it wasn't just about teaching people to use AI tools—it was about helping entire organizations understand how AI was going to change their work."

Hiring People Who Don't Need Answers

Scaling a company through rapid growth is challenging. Scaling while your entire market is being redefined requires a specific type of person.

Grassi doesn't hire for people who want structure or clear role definitions. He looks for people who get energy from figuring things out as they go.

"We hire people who thrive on challenges. People who are passionate about learning, who want to make an impact, and who aren't afraid of ambiguity. Because right now, that's what we're dealing with every day."

General Assembly operates globally, serving enterprise clients in one time zone, government organizations in another, and individual learners scattered everywhere. The work requires constant context-switching between different industries, different buying processes, different definitions of success.

"You have to be comfortable working across different time zones, different cultures, different types of customers. That's not for everyone. But for the people who love it, it's incredibly rewarding."

This isn't the generic "fast-paced environment" language that shows up in job postings. Grassi is describing what happens when you're building training programs while the technology you're teaching is still evolving, or when you're explaining AI applications to industries you didn't know existed six months ago.

Saying No to Shiny Objects

When demand started coming from every direction, General Assembly had to get disciplined about what they would and wouldn't chase.

"It would have been easy to chase everything. But we had to be disciplined. We had to ask: What are we uniquely positioned to solve? Where can we actually add value?"

The answer was practical skills training. General Assembly wasn't going to become a consulting firm or a research lab or a thought leadership platform. They were going to teach people how to actually use AI in their jobs, right now.

"We're not here to teach people about AI in the abstract. We're here to teach them how to use it to do their jobs better."

That focus became a filter. Consulting engagements that didn't fit the model got turned down. Partnership opportunities that would dilute their expertise got passed on. The discipline paid off. General Assembly now trains tens of thousands of people annually across Fortune 500 companies, governments, and individual learners worldwide.

"Every single organization is trying to figure out what AI means for them," Grassi says. "And most of them are way behind where they need to be. That's where we come in."

What It Actually Feels Like

Working at General Assembly right now means operating at the center of a massive workforce transformation. You might design curriculum in the morning, run a workshop for a European government agency in the afternoon, and debrief with enterprise clients on the West Coast in the evening.

"You're at the center of one of the biggest transformations in how we work. You're helping companies and governments figure out what the future looks like. That's not a job where you coast."

The pace is relentless. The company operates across time zones, which means the work doesn't stop at 5 p.m. But Grassi says that for the right person, that's precisely the appeal.

The learning culture extends internally as well. General Assembly practices what it preaches—everyone on the team is constantly upskilling, adapting to new tools and approaches as the technology evolves.

"We practice what we preach," Grassi says. "Everyone here is constantly learning, constantly adapting. If you're not curious, you're not going to like it here."

Looking Ahead

Grassi sees the need for AI skills as permanent, not temporary. Every organization is trying to understand how this technology changes their work, and most are still in the early stages of that process.

"We used to think about our mission as helping people start careers in tech. Now, it's much bigger. It's about preparing everyone—in every industry, in every role—for a world where AI is part of their job."

That means continuing to evolve the curriculum as the technology changes. It means expanding into new markets and finding ways to make skills training more accessible. It also means staying humble about what they don't know.

"We're figuring this out in real time, just like everyone else. But we have a front-row seat to how the workforce is changing. And that gives us an incredible opportunity to help shape what comes next."

Final Tips for Founders, Recruiters, and Job Seekers

Founders — When market disruption hits, pay attention to inbound demand from unexpected customer segments. These requests may signal that your addressable market is expanding in ways you hadn't planned for.

Recruiters — When scaling globally, look for candidates who thrive on ambiguity rather than structure. Ask specific questions about times they've built something without clear guidelines or operated effectively across different contexts.

Job Seekers — Before joining a company navigating major market shifts, ask yourself whether you get energized or drained by uncertainty. The right answer depends on what kind of work environment helps you do your best work.

Watch the full conversation between Amit Matani and Daniele Grassi here

Why Work Here is a series in which Amit Matani, CEO of Wellfound, has honest, behind-the-scenes conversations with founders, executives, and employees about why their companies are worth joining. Click here to watch more Why Work Here.