In the ever-evolving hustle of the Pacific Northwest’s tech landscape, where innovators and executives dance across job titles like chess pieces on a grand board, February 2026 brought a fresh wave of career shifts and recognitions. It all started with high-profile exits and entries that reminded everyone why Seattle’s ecosystem feels like a living, breathing organism of ambition. Cynthia Tee, the steady hand behind Smartsheet’s technological heartbeat for nearly half a decade, decided to step away from the work management giant based in Bellevue. The company, still reeling from layoffs earlier that month and a CEO transition from Mark Mader to tech veteran Raj Singh, kept things low-key. Their spokesperson thanked Tee for her contributions without naming a successor, leaving the air thick with unspoken possibilities. Tee, who hadn’t landed a new gig yet according to her own words, reflected on a career rooted in Microsoft’s Windows world back in 1994, followed by stints at Nordstrom and even volunteering as executive director at Seattle’s Ada Developers Academy—a place empowering underrepresented folks in tech through free bootcamps. It was a bittersweet moment for her admirers; Tee wasn’t just a CTO, she was a connector, bridging corporate might with grassroots initiative. Her departure echoed broader themes of change, where even titans like her pivot not for drama but for renewal, perhaps seeking quieter challenges or entrepreneurial ventures. But amidst the goodbyes, new faces emerged, injecting energy into defense tech. Mark Dewyea, a Virginia-based lawyer with a Marine Corps and FBI background, joined Overland AI, the Seattle startup crafting autonomous ground vehicles for the U.S. military. Hired as head of legal after his role at Shield AI, Dewyea’s hire felt like a strategic arming of the company, which spun out from the University of Washington in 2022 and just secured $100 million in funding. His LinkedIn promo highlighted a resume steeped in duty and defense, painting him as a bridge between bureaucracy and battlefield innovation. Meanwhile, Jessica Roberto traded academia for state service, becoming the Knowledge Economy Lead at Washington’s Department of Commerce. Her six years at the UW’s Buerk Center for Entrepreneurship, managing graduate programs and innovation challenges, equipped her with a PhD in pathobiology and a knack for fostering startups. This move wasn’t just a job hop; it symbolized a scholar’s call to policy, where her insights could shape economic tides for the region. Heather Redman, co-founder of Flying Fish venture firm, took a seat on the Seattle branch board of the San Francisco Fed, blending VC prowess with central banking oversight. These transitions weren’t isolated explosions but threads in a tapestry of professional reinvention, where each individual’s path revealed the unpredictable beauty of career trajectories in a tech hub that demands adaptability.
Diving deeper into the corporate corridors, promotions and lateral leaps showcased the internal engines powering companies from airlines to cloud behemoths. Anna Fuller, Seattle’s own tech entrepreneur, transitioned from leading product at California-based Big Sur AI—snapped up by Google at year’s end—to building out commerce AI at the search giant itself. Her dual role as a resident expert at AI2 Incubator, home to the burgeoning AI House on the waterfront, highlighted her as a nexus of commercialization and experimentation. Fuller embodied the restless innovator, ever chasing the next frontier where AI meets mundane transactions, turning abstract algorithms into everyday tools. Over at Alaska Airlines, Ben Brookman soared to vice president of real estate and airport affairs after over a decade with the carrier in two stints, punctuated by gigs at Convoy and Amazon. His ascent felt earned, a testament to perseverance in aviation’s turbulent skies. Keith Turner, a Comcast veteran of nearly two decades, was named senior VP for the Pacific Northwest region, overseeing Xfinity and Comcast Business across Washington and Oregon. These elevations weren’t mere title bumps; they signaled trust in seasoned players to navigate regional complexities, from Wi-Fi woes in rainy suburbs to cloud expansions in eco-conscious hubs like Portland. Rebecca Amos-Stuart, after six-plus years at Zillow and earlier runs at Verizon and her own consultancy, climbed to marketing director in the Seattle area, touting real estate tech forward. Each story here unfolded like a personal odyssey, where experience met opportunity, reminding us that behind corporate ladders are people with histories as rich as the PNW’s storied hills—individuals who’ve weathered layoffs and acquisitions, emerging stronger to steer ships through digital tempests.
As startups flexed their muscles and expanded footprints, the scene crackled with expansionist energy, particularly in child welfare and music realms. Cam Caldwell, chief operating officer of San Francisco’s Binti, relocated to oversee the company’s freshly minted Seattle office. Binti’s tech, aimed at bolstering child welfare systems, found a new home amid the city’s rainy countenance, and with it came hiring calls that echoed promises of impact. This wasn’t tokenism; Caldwell’s arrival breathed life into a venture prioritizing vulnerable populations, turning code into compassion. Across town, music licensing outlier Incantio snagged Virl Hill for its board, the media exec’s résumé brimming with Microsoft, RealNetworks, and Disney stints. Hill, previously on Incantio’s advisory board, brought a Hollywood polish to a startup reimagining how tunes get licensed in our media-saturated age. These additions painted a picture of tech not as cold silicon but as human enterprise, where offices become beating hearts of change. Firms like Baker Sterchi Cowden & Rice added Brian Maxey as senior counsel in Seattle, drawing on his ex-COO tenure at the Seattle Police Department to advise public sector clients on risks, crises, and litigation. Even Yoodli, the AI roleplay venture, welcomed Vija Veingbergs-Rogers as a senior software engineer from neurology outfit Rune Labs, her skills poised to refine conversational AI. These hires felt intimate, like assembling a dream team for societal puzzles—child protection, artistic freedom, public safety, and empathetic tech—all under the Pacific Northwest’s umbrella, where idealism meets intrepid growth.
Boardrooms too became arenas of influence, with appointments weaving threads of expertise into governance. Incantio’s board boost with Hill was one strand; the national spotlight on engineering elites added luster. The National Academy of Engineering elected 130 luminaries, including a quartet tied to the PNW: UW’s Nobel-winning David Baker, crafting de novo proteins via AI at the Institute for Protein Design; Microsoft Research’s Douglas Burger, innovating cloud-scale setups with programmable systems; Amazon’s James Hamilton, pioneering efficient cloud computing and data centers; and retired Boeing SVP Elizabeth Lund, who shaped twin-aisle airplanes through dedication to production and quality. These inductions celebrated lifetimes of brilliance, ennobling figures who transformed abstract ideas into tangible progress, from biotech breakthroughs healing diseases to aviation feats connecting continents. Locally, the Oregon Entrepreneurs Network expanded its 18-member board with five new additions, injecting fresh voices into the state’s entrepreneurial chorus. These roles weren’t mere honors; they embodied mentorship and oversight, guiding ventures through valleys of doubt toward peaks of success. In Heather Redman’s Fed seat, one saw a VC mogul lending gravitas to monetary policy, her Flying Fish adventures informing discussions on fiscal futures. Collectively, these elevations humanized innovation’s facade, revealing how power plays unfold not in isolation but through collaborative narratives, where a board seat or academy medal signifies trust in potential to inspire generations.
Beyond the spotlight, these stories hinted at deeper currents of community and aspiration, where personal journeys fueled regional resurgence. Cynthia Tee’s post-Smartsheet pause, for instance, mirrored broader reflections in an industry of relentless motion—perhaps prompting her to mentor at Ada anew, amplifying voices too often muted. Mark Dewyea’s military rigor brought discipline to Overland AI’s bold autonomy pushes, a nod to veterans reshaping civilian tech with disciplined vision. Jessica Roberto’s policy pivot highlighted how academic rigor translates to public good, her UW roots nurturing economic vitality. Anna Fuller’s Google stint, building on Big Sur’s acquisition, underscored serial innovation’s thrill, her AI House affiliations fostering incubators that democratize creation. Promotions like Rebecca Amos-Stuart’s at Zillow celebrated quiet persistence, transforming marketing from buzz to belonging. These arcs, from Dewyea’s forensic acumen to Roberto’s scholarly depth, underscored the PNW’s alchemy: melting down expertise into new forms, resilient against layoffs and acquisitions. Even as Overland AI secured fresh millions, it invited pondering how funding fuels dreams—vehicles rolling off assembly lines or startups scaling ethically. In this ecosystem, board inductions at Incantio or the Academy weren’t culminations but chapters, each figure a storyteller urging others upward.
Ultimately, this February snapshot captured the Pacific Northwest’s tech soul: resilient, interconnected, and profoundly human. Departures like Tee’s evoked nostalgia for paths taken, yet openings like Roberto’s at Commerce beckoned bravery. National kudos for Baker, Burger, Hamilton, and Lund reminded that excellence transcends geography, inspiring local dreamers to aim high. Oregon’s network expansions and Seattle hires at Binti and Yoodli signaled grassroots momentum, where music licensing met child advocacy in a symphony of progress. Entrepreneurs like Fuller symbolized fluidity, career-jumping with purpose, her AI passions bridging Big Sur’s past to Google’s present. Turner’s Comcast stringency and Brookman’s aviation ascent illustrated steady climbs, rewarding fidelity amid industry churn. Hill’s media savvy and Redman’s Fed influence enriched boards, voices amplifying community needs. Maxey’s public sector insights protected against crises, while Caldwell’s Binti tenure humanized tech for welfare systems. In aggregate, these narratives wove a richer tale than headlines alone—a region where careers weren’t fixed but fluid rivers, carving valleys of opportunity. Each move reflected aspirations: Tee’s legacy influencing future leaders, Dewyea’s defense work advancing security, Roberto’s policy work nurturing jobs. A hundred years from now, historians might see 2026 as a pivot point, where tech titans and unsung heroes alike redefined “progress” not as code or cash, but as people pursuing purpose in partnership with their neighbors under ever-shifting skies. And in that spirit, the PNW pulsed onward, a testament to adaptability’s quiet power, transforming individual strides into collective strides toward brighter horizons.
