5 acquisitions, winning over skeptical engineers, and spending tens of millions: Inside a public company's 'AI native' push

• Amplitude gave Business Insider an inside look at its AI overhaul, from acquisitions to employee upskilling.
• CEO Spenser Skates said he overcame his own initial skepticism of the tech and invested tens of millions in AI integration.
• It's a change that hundreds of white-collar businesses are going through: trying to become "AI native."

There's a long banner hanging in Amplitude's San Francisco office. It reads: "NO MAGICAL THINKING."

No, it's not some rag on Joan Didion. It's a reminder, CEO Spenser Skates told Business Insider, that technology can never replace deep thinking and hard work. In the AI age, that reminder is more important than ever — so much so that employees must look up at it every day.

Amplitude, an 800-person, publicly traded analytics company, is undergoing an AI transformation — with the goal of reinvigorating its business.

Amplitude went public in September 2021 at the height of the pandemic, climbing to an all-time closing high of $84.80 per share several weeks later before dropping significantly and largely plateauing in in recent years around $10. It closed at $10.25 on Friday.

Since October 2024, the company has acquired five AI startups. Amplitude hired an AI-savvy engineering head and appointed one of its acquired founders to a new AI leadership position. It got Cursor and GitHub Copilot licenses for employees, and ran a heads-down AI week.

It's a change many companies are making: Rapidly moving from little-to-no AI to trying to become "AI native," a term that's curiously hard to pin down. Large language models are popping up everywhere in white-collar work as companies chase the promise of efficiency gains.

Amplitude's case may be especially informative, given just how skeptical of AI its CEO was. In 2023 and some of 2024, Skates said he viewed the AI industry as full of "grifters," the visionaries promising to end world hunger and salesmen promising to automate everything.

"It had all sorts of problems," Skates said. By mid-2024, he realized "there's probably going to be a breakthrough in the analytics space in the next two or three years."

"We've got to go make that ourselves," he said. "So, we went all in."

'Tens of millions' poured into an AI overhaul

Skates had two opening moves for his AI overhaul.

The first: hiring a new chief engineering officer with a history in AI. Wade Chambers had advised the company since 2016, while holding leadership roles at Twitter and Included Health.

When Chambers joined in October 2024, only 1% of the engineering, product, and design teams at Amplitude were using AI.

The second was the acquisition of Command AI, a chatbot startup. It was the first of a string of acquisitions, including June, Kraftful, and Inari. Amplitude announced its most recent acquisition, InfiniGrow, on January 14.

Yana Welinder was CEO of Kraftful, one of Amplitude's acquisition targets. Kraftful could spot power users of its product, one of whom was Amplitude's then-CPO. She reached out, and they chatted in February. The deal closed in July, and Welinder was named Amplitude's head of AI. A company blog post with an introductory Q&A referred to her as "AI maven."

Welinder's first order of business: speeding the company up. Kraftful shipped new product every week. Amplitude was shipping less than monthly.

"If you have this cadence of shipping infrequently, then the team slows down, which isn't appropriate in the age of AI," she said.

By October, Skates had sent his official email to staff. Its title was "Introducing: AI Native Amplitude."

"Analytics will look very different 6 months from now," Skates wrote in his email. "We have the opportunity to be the AI native company in Analytics and we are going to pull every piece of firepower we have."

He also asked employees to share a coming launch on X, as opposed to LinkedIn, because that's "where the AI natives are."

How much has Amplitude spent on AI, from tools to acquisitions? "Tens of millions, for sure," Skates said. "I wouldn't be surprised if it got past $100 million."

How to change an AI skeptic's mind

Then comes the harder part: convincing employees to really use the tools.

While some engineers are excited about AI's promise, others are skeptical about its helpfulness, or worried about possible job losses. Not every engineer is as gung ho about AI as their management is.

Skates said that engineers were especially sensitive to the "grifting" that went on in AI, making many of them skeptical. With a bottoms-up approach, that skepticism dissipates, he said.

Soon after joining, Chambers began planning an "AI week" for the first week of June. It took six months of prep and borrowed heavily from Facebook's mobile push. He took the entire engineering, product, and design team offline for the week. To kick off, Chambers required that leaders get onstage and vibe-code something in front of the entire company.

"It didn't go well," Chambers said of the live vibe-coding demonstration. "They had to work through it. They had to re-prompt a couple of different ways."

But the message stuck, he said. Leaders who weren't coding all day were able to build something "pretty cool" within the hourlong session, save a few hiccups.

Additional momentum came from the "zealots," engineers passionate about exploring the new tech (some of whom Chambers brought over from his prior job). These engineers lead by example, he said.

Amplitude shared its internal data tracking how many employees use its AI tools. In the final week of March, 14 employees were actively using Cursor. That figure peaked in the first week of December — after AI week but before the holiday vacation cycle — at 174 employees.

And what of the thorny question about AI implementation in the enterprise: ROI? After all, a 2025 MIT study indicated 95% of firms publicly disclosing use of AI pilots reported no measurable ROI.

After implementing these tools, developer productivity shot up 40% and stayed there, Chambers said. On some specific engineering teams, those gains looks more like 300-400%, he said.

"There's going to be a lot of people who are thinking they're the world's best expert at something," Chambers said. "Increasingly, even the most cynical team members have come around."