According to GeekWire, Steven Maheshwary, a former generative AI leader at Amazon with 12 years at the company, has joined AI giant Anthropic as a go-to-market lead. At the same time, Microsoft’s longtime government affairs director Irene Plenefisch is retiring after more than 15 years there. In Seattle city government, Brian Surratt is now the official deputy mayor under new Mayor Katie Wilson, who was sworn in last Friday. Other moves include Nikhil Hasija leaving his VP of engineering role at Okta, Caitlin Rollman returning to Microsoft as a partner product manager, and Joseph Williams stepping down as interim director of the Washington State Broadband Office. The article also notes that Commerce Director Joe Nguyen is leaving to become president and CEO of the Seattle Metropolitan Chamber of Commerce.
AI Talent Is The New Currency
Look, the Maheshwary move is the headline grabber here for a reason. An Amazon AI leader jumping to Anthropic, which Amazon has invested billions in? That’s juicy. It shows the insane competition for people who actually understand how to build and, crucially, commercialize foundation models. His quote about AI being a “raw energy that must be shaped” is pure Anthropic messaging—safe, capable, aligned. He’s not just changing jobs; he’s buying into a specific philosophical camp in the AI wars. And you have to wonder, does this make the Amazon-Anthropic partnership even tighter, or does it create a new kind of friction?
The Great Reshuffle Continues
But it’s not just AI. The whole piece reads like a snapshot of a tech ecosystem in constant, churning motion. You’ve got the classic “boomerang” story with Caitlin Rollman going back to Microsoft after trying her hand at a startup and another company. That happens all the time, but it speaks to the gravitational pull these giants still have. Then there’s Nikhil Hasija leaving Okta after an acquisition—another super common arc. Founder stays for a bit, then gets the itch to build again. His comment about being drawn to “leverage, speed, and new ways of working” is basically the universal code for “I’m going to a startup or starting something new.”
Policy And Politics In The Mix
Here’s the thing that’s easy to miss: the deep connections between tech and policy in this region. Plenefisch’s retirement from Microsoft’s government affairs is a big deal—that’s institutional knowledge walking out the door. And then you have Brian Surratt, who’s been in the economic development game for years in both the public and private sector, stepping into the deputy mayor role. His LinkedIn statement is a masterclass in political messaging, hitting all the key Seattle issues: homelessness, housing, trust. It shows how the skills of building coalitions and selling a vision are the same whether you’re pushing a tech product or a city policy. It’s all about influence.
What’s The Bigger Trend?
So what does all this mean? Basically, the Pacific Northwest tech scene remains a small world where everyone has worked at Microsoft or Amazon at some point. The career paths are incredibly fluid: big tech to startup, back to big tech, into government, into nonprofits like Coltura. The lines are totally blurred. And with high-profile departures from state government (Nguyen, Williams), there’s a parallel reshuffling happening in the public sector that will directly impact how tech does business in Washington. All these moves set the stage for the rest of the year. Who’s building the next big thing? Who’s shaping the rules they’ll have to play by? This list gives us a few clues.
