Satish Thomas, a 20-year veteran of Microsoft who spent two decades at the Redmond tech giant, is taking a new job at Google.

“I’m joining during what feels like one of the most consequential moments in tech history — right in the heart of the AI era,” Thomas wrote on LinkedIn. He did not specify what role he’s taking at Google.

Thomas said Microsoft “shaped me in ways I never imaged.” He began his two-decade run at the company as an intern. “I’m deeply grateful to the amazing people and teams I’ve had the privilege to work with,” he said. “Leaving isn’t easy — but some opportunities are so special and unique that you just have to go for them.”

Thomas spent the past six years as a corporate vice president at Microsoft, where he led strategy, product management, and engineering execution for Microsoft Cloud for Industry. He previously held leadership roles in Microsoft Dynamics 365 and Microsoft AppSource.

— Raji Rajagopalan has a new role at Microsoft: GitHub’s vice president of engineering.

Rajagopalan has been with the tech giant for more than 20 years, joining the company as a software engineer. She’s leaving the Microsoft Foundry Team for the new role.

“My goal is to help GitHub continue to be the place loved by devs, where innovation happens and human-agent workflows thrive, as we move into this new era of AI-driven development,” Rajagopalan said on LinkedIn.

— Katie Bardaro is senior VP of customer experience at Avante, a Seattle startup building software to help companies decrease HR administration workload and reduce overall benefits program costs. It also offers an AI assistant designed to provide benefits guidance to employees.

“What drew me here is the opportunity to work at the intersection of data, AI, and total rewards, all while helping companies and employees navigate one of the most complex (and impactful) parts of the employee experience: benefits,” Bardaro said on LinkedIn.

Bardaro was previously chief customer officer at Syndio, a company that analyzes workplace pay equity issues and provides strategies for fixing disparities. Prior to that she was at Payscale for more than a decade.

— Vivek Sharma is leaving Stripe for a cryptic new venture focused on “AI’s potential to fundamentally change how people work.”

Sharma, who has held executive roles at Microsoft and Meta, didn’t provide further details about the stealthy startup in a LinkedIn post, but did name his collaborators:

• Tore Hanssen, who was a founding engineer at Statsig, the Bellevue, Wash.-based startup acquired in September by OpenAI. He previously worked at Meta.
• Robert Masson, a senior staff data scientist at Meta’s Seattle office, clocking nearly 11 years with the company before going to Atlassian early last year.
• Calvin Grunewald, who spent nine years as a Facebook director of engineering, based in Seattle. He was most recently at Stripe.

“More details coming soon,” Sharma said of the startup. “But if you want to be an early adopter or just want to chat, please reach out!”

— Jeff Carr is now CEO of Atana, a startup building workplace training content that incorporates behavior-based learning and development. Carr joined the Bellevue company in August as president. He succeeds Atana co-founder and former CEO John Hansen, who will remain as executive chair.

In announcing the news, Hansen said that Carr “aligned with Atana’s vision immediately and has been instrumental in bringing us into new opportunities and new strategic relationships in a very short period of time.”

Carr has held multiple CEO roles in the past, including leadership of workforce training company Inkling and at the HR company PeopleFluent.

Atana originally launched in 1993. Hansen, a startup veteran and longtime lecturer at the University of Washington, acquired the business in 2016 and oversaw the expansion of new learning content.

— Longtime Microsoft gaming leader Larry Hyrb shared on LinkedIn that he was laid off from Unity after 18 months on the job.

Hyrb, known by his longtime handle “Major Nelson,” left Microsoft in 2023 after more than two decades in corporate communications, promoting the launches of games and other products. He was the host of one of the company’s earliest podcasts, Major Nelson Radio, which later became Xbox Podcast.

At Unity, a San Francisco-based gaming company, Hyrb worked with the Community and Advocacy Team, supporting connections among creators, developers and gamers.

— Serial tech entrepreneur Jay Bartot is now a technical advisor and chief technologist for TheFounderVC, a Seattle-based venture capital firm that launched in 2024.

Bartot is also co-founder and CTO of the software startup AirSignal, an affiliate professor at the UW, and a startup mentor at Creative Destruction Lab.

Bartot said on LinkedIn that he looks forward to working with the TheFounderVC team “to help exceptional early-stage founders build the next generation of great Vertical AI companies and products.”

— Auger, a startup building logistics and supply chain software, named Tucker Reimer as principal of supply chain innovation. Reimer joins the Bellevue startup from the Johnsonville sausage company where he served as vice president of global planning and analytics.

Dave Clark, the former Amazon Worldwide Consumer CEO and Flexport CEO, launched Auger in 2024 with $100 million in Series A funding.

— Lucas Dickey joined Stripe as a product builder focused on Stripe Atlas, a tool that helps entrepreneurs incorporate their business.

Dickey said on LinkedIn that he has used Atlas four times to start his own companies and aligns with Stripe’s goal of “making the administrative layer a breeze — and helping new companies start strong from day one.”

His startups include Deepcast, a podcast platform, and Fernish, a decor-focused business that was acquired.

[Editor’s Note: Agents of Transformation is an independent GeekWire series and March 24, 2026 event, underwritten by Accenture, exploring the people, companies, and ideas behind AI agents.]

Microsoft is making its own bid to turn AI conversations into agentic commerce, announcing a new feature called Copilot Checkout that lets users complete purchases directly within its AI chatbot, without being redirected to an external website.

The company is betting that its existing enterprise technology footprint and established relationships with large retailers will give it an edge over OpenAI, Google, and Amazon in winning over merchants wary of giving up control to retail rivals or AI intermediaries.

“We’ve designed it in such a way that retailers own those relationships with the customers,” said Kathleen Mitford, corporate vice president of global industry marketing at Microsoft. “It is their data, it is their relationship, and that’s something that’s really important to us.”

It’s part of a broader AI rollout by Microsoft at NRF 2026, the retail industry’s annual conference in New York. Microsoft is also launching Brand Agents, pitched as a complete solution for Shopify merchants to add AI assistants to their websites, along with new AI tools to assist store employees and help retailers enhance their online product listings and metadata.

Copilot Checkout works by surfacing products from partner retailers within Copilot search results. Purchases can be completed without leaving the conversation. Microsoft says the retailer remains the merchant of record, handling fulfillment and customer service.

But will people buy in chat?

The bigger question for the tech industry is whether chat-based commerce is actually the next big thing. Forrester analyst Sucharita Kodali, for example, previously told GeekWire that “e-commerce isn’t a problem that needs to be fixed.” She added that it’s unclear what value chat-based commerce is bringing to retailers, “other than disintermediating Google.”

Microsoft’s Mitford offered a different take in an interview this week, saying that consumer behavior is shifting faster than it may seem. She drew a parallel to how quickly businesses moved from experimenting with AI to putting it into operation over the past year.

“I see the same thing happening with consumers … it just takes a little bit of time,” Mitford said, predicting that the speed of consumer adoption will eventually match the rapid uptake seen in the business world.

Copilot Checkout is rolling out now in the U.S. on Copilot.com, with PayPal, Shopify, and Stripe handling payment processing. Etsy sellers will be among the first available on the platform. Shopify merchants are set to be automatically enrolled following an opt-out window.

That last detail is notable given the backlash Amazon has faced over its “Buy for Me” feature, where brands complained about being included without consent and seeing inaccurate listings. 

Microsoft’s approach is more tightly connected to its partners — the company said Shopify will management the opt-out process for its merchants — but automatic enrollment seems to raise the potential for some of the same concerns. (We’ve contacted Shopify for more information.)

The competitive landscape

More broadly, Microsoft is playing catch-up on the consumer side.

OpenAI launched Instant Checkout in ChatGPT last September, partnering with Shopify and Stripe to let users buy from more than a million merchants. Google followed in November with its own “Buy for Me” feature which lets its Gemini assistant purchase products on a user’s behalf.

Despite its inroads with businesses, Copilot has a fraction of ChatGPT’s market share with consumers. Recent data from Similarweb’s Global AI Tracker showed ChatGPT with about 68% of AI chatbot web traffic, with Google Gemini at 18% and Copilot in the single digits.

But Microsoft has its advantages: Unlike Amazon and Google, which compete directly with retailers through their own marketplaces, it isn’t a retailer. And retail has long been a major vertical for its enterprise cloud and software business, with large chains running on Azure and Microsoft 365.

Mitford said Microsoft is leaning on its existing trust and long-standing relationships with retailers, along with a commitment to responsible AI, to help differentiate itself from rivals.

Microsoft is making the broader case for AI to retailers based on return on investment. A Microsoft-commissioned study from IDC, released in November, found that retail and consumer packaged goods companies are seeing a 2.7x return on every dollar spent on generative AI.

Mitford, a former fashion designer who has been in the technology industry for most of her career, said she sees the retail sector among the leaders in AI uptake across the business world.

The technology, she said, is being “adopted at a pace that I’ve never seen.”

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