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Smartsheet CTO Cynthia Tee departs; Overland AI names legal lead, with moves at Zillow and Comcast

A February 2026 Pacific Northwest roundup included Cynthia Tee’s departure from Smartsheet, a legal hire at Overland AI, and moves at Comcast and Zillow.
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A February 2026 Pacific Northwest executive roundup included the departure of Smartsheet CTO Cynthia Tee, Overland AI’s appointment of Mark Dewyea as head of legal, and leadership moves at Comcast and Zillow. The developments were reported by GeekWire on February 13, 2026; they span a departure, a hire and internal promotions rather than a single coordinated shift.

Smartsheet CTO Cynthia Tee leaves the company

Cynthia Tee left Smartsheet after serving as chief technology officer since February 2025. Before becoming CTO, she was the company’s senior vice president of engineering for nearly four years. Her earlier career included nearly two decades at Microsoft, a vice president of commerce technology role at Nordstrom, and service as executive director of Ada Developers Academy. GeekWire reported the departure on February 13, 2026.

At that time, Smartsheet had not publicly explained the departure, given an effective date, or announced a replacement or interim CTO. Tee told GeekWire she had not accepted another role. The company’s leadership change came after Rajeev “Raj” Singh became CEO in October 2025, succeeding Mark Mader, who retired. GeekWire also reported layoffs earlier in February; the available reporting does not establish that the layoffs caused Tee’s departure.

Smartsheet’s current leadership roster lists Pratima Arora as chief product and technology officer. That current title does not, by itself, confirm that Arora was appointed Tee’s direct successor. Smartsheet’s 2025 leadership announcement had identified Arora as chief product officer and Nick Dunn as general counsel, but did not establish a succession relationship with Tee.

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Overland AI hires Mark Dewyea as head of legal

Seattle-based defense startup Overland AI named Mark Dewyea head of legal. He previously worked at Shield AI as chief of staff and in-house counsel. His background also includes active-duty service as a U.S. Marine Corps judge advocate and work as a legal analyst at the FBI. GeekWire, citing Overland AI’s LinkedIn announcement, described him as Virginia-based.

Overland AI develops autonomous ground vehicles for military use and spun out of the University of Washington in 2022. GeekWire reported that the company announced $100 million in new funding earlier in February 2026. A legal leader can be especially relevant as a defense company works with government and military customers: procurement, contracting, export controls, intellectual property, cybersecurity and product liability can all raise specialized legal questions. Those are contextual reasons the appointment may matter, not a confirmed list of Dewyea’s specific duties; the reported title is head of legal, not general counsel.

Comcast names Keith Turner to lead its Pacific Northwest region

Comcast named Keith Turner senior vice president of its Pacific Northwest region, covering Washington and Oregon. The role includes Xfinity and Comcast Business customers. Turner had been with Comcast for nearly two decades, according to GeekWire’s February 13 report.

The appointment places a regional executive over operations serving both residential and business customers in the two states. That remit connects the role to local broadband service, business connectivity and relationships with regional markets; the report does not detail any change to Turner’s specific authority or prior assignment.

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Zillow promotes Rebecca Amos-Stuart to marketing director

Zillow promoted Rebecca Amos-Stuart to marketing director. She had spent more than six years at Zillow, previously operated her own consulting business, and worked at Verizon for 12 years. GeekWire identified her as Seattle-area based. The report gives the new title but does not specify an expanded portfolio or reporting structure.

Other notable Pacific Northwest moves

The same roundup included appointments and career moves across government, startups, aviation, business and professional organizations. These were not all executive hires or promotions:

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  • Government and civic roles: Jessica Roberto joined the Washington State Department of Commerce as knowledge economy lead. Heather Redman joined the Seattle branch board of directors of the Federal Reserve Bank of San Francisco.
  • Companies and startups: Anna Fuller moved to Google’s commerce-AI work after Big Sur AI’s acquisition. Alaska Airlines promoted Ben Brookman to vice president of real estate and airport affairs. Cam Caldwell took charge of Binti’s newly opened Seattle office. Incantio appointed Virl Hill to its board, Baker Sterchi Cowden & Rice named Brian Maxey senior counsel in Seattle, and Vija Veinbergs-Rogers joined Yoodli as a senior software engineer.
  • Professional recognition and nonprofit leadership: Four Pacific Northwest engineers were elected to the National Academy of Engineering, and Oregon Entrepreneurs Network appointed five new board members.
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What the reported moves establish—and what they do not

Person Organization and move Not established in the reporting
Cynthia Tee Departed Smartsheet’s CTO role Reason or effective date; a direct successor at the time of publication
Mark Dewyea Named head of legal at Overland AI Exact reporting line or full scope of responsibilities
Keith Turner Named Comcast senior vice president for the Pacific Northwest Whether the move was a promotion or reassignment, and details of any authority change
Rebecca Amos-Stuart Promoted to Zillow marketing director Expanded responsibilities or reporting structure

The moves involve public companies, a defense startup, a regional service provider, public institutions and local organizations. They show varied personnel activity across the Northwest, but do not by themselves establish a broader hiring trend or coordinated change in strategy.

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