Cynthia Tee Departs Smartsheet as CTO Amid Leadership Shakeup

In a significant leadership change at one of Seattle’s most prominent enterprise software companies, Cynthia Tee has stepped down from her role as Chief Technology Officer at Smartsheet, the Bellevue-based work management platform that has become a cornerstone of modern business operations.

Tee’s departure marks the end of a transformative tenure at the company. She assumed the CTO position in February 2025, following nearly four years as Senior Vice President of Engineering, where she played a pivotal role in scaling Smartsheet’s technical infrastructure to support its growing enterprise customer base. During her leadership, the company expanded its AI capabilities and enhanced its platform’s scalability to handle millions of users globally.

“I have not taken a new role elsewhere,” Tee told GeekWire, leaving the tech community speculating about her next move. Her departure comes at a time when Smartsheet is navigating significant changes under new leadership, having recently undergone layoffs and a CEO transition.

A Storied Career in Tech

Tee’s journey through the technology sector spans over two decades, beginning with a 20-year stint at Microsoft where she joined in 1994. During her time at the Redmond giant, she worked extensively on Windows technologies, contributing to some of the company’s most foundational products. Her Microsoft experience provided her with deep expertise in building and scaling complex software systems that would later inform her leadership at Smartsheet.

Before joining Smartsheet, Tee served as Vice President of Commerce Technology at Nordstrom, where she led digital transformation initiatives in retail technology. This experience in both enterprise software and retail technology positioned her uniquely to understand the intersection of business operations and technical innovation.

Tee’s commitment to diversity in tech extends beyond her corporate roles. She served as Executive Director of Seattle’s Ada Developers Academy, a tuition-free tech bootcamp dedicated to training women and other underrepresented groups in technology. Her involvement with Ada reflects her dedication to building a more inclusive tech ecosystem in the Pacific Northwest.

Smartsheet’s Recent Turbulence

Tee’s departure occurs against the backdrop of significant changes at Smartsheet. The company recently conducted layoffs, though the exact number of affected employees remains undisclosed. These workforce reductions come as the company continues to invest heavily in AI and automation capabilities to maintain its competitive edge in the crowded work management software market.

The leadership transition at Smartsheet accelerated in October 2025 when Rajeev “Raj” Singh took over as CEO. Singh, a veteran enterprise software executive, returned to his roots in the Seattle area to lead the company. His appointment followed the announcement that longtime CEO Mark Mader would retire, marking the end of an era for the company he helped build from a small startup into a publicly traded enterprise software giant.

Under Mader’s leadership, Smartsheet grew from a spreadsheet-inspired collaboration tool into a comprehensive work management platform used by millions of knowledge workers across industries. The company’s IPO in 2018 and subsequent growth established it as one of the Pacific Northwest’s most successful enterprise software companies.

Industry Context and Implications

Tee’s departure raises questions about the strategic direction of Smartsheet’s technology organization. As CTO, she was responsible for the company’s technical vision and execution, particularly as Smartsheet competes with giants like Microsoft, Asana, and Monday.com in the work management space.

The timing of her exit is particularly noteworthy given the industry-wide push toward AI-powered productivity tools. Smartsheet has been investing in AI capabilities to enhance its platform’s automation features and provide more intelligent insights to users. Tee’s technical leadership was instrumental in these initiatives, and her departure may signal a shift in how the company approaches its AI strategy.

For the broader Seattle tech ecosystem, Tee’s move represents another high-profile executive transition in a region that continues to be a hub for enterprise software innovation. Her experience across Microsoft, Nordstrom, and Smartsheet provides a unique perspective on how large organizations approach digital transformation and technical leadership.

Looking Ahead

As Smartsheet searches for Tee’s replacement, the company faces the challenge of maintaining technical momentum while adapting to new leadership priorities. The enterprise software market remains highly competitive, with customers demanding increasingly sophisticated features around collaboration, automation, and AI integration.

Tee’s next steps remain unclear, but her track record suggests she will continue to play a significant role in shaping the future of enterprise technology. Whether she joins another major tech company, pursues entrepreneurial ventures, or returns to focus on diversity initiatives in tech, her experience and leadership will undoubtedly be in high demand.

The Pacific Northwest tech community will be watching closely to see how Smartsheet navigates this transition and what opportunities Tee pursues next. Her departure marks not just a leadership change at one company, but a moment of transition for an executive whose career has been deeply intertwined with the evolution of Seattle’s technology landscape.

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