— Drew Garner is now senior vice president of engineering for Smartsheet.

Garner joins the Bellevue, Wash., work productivity software giant as Rajeev “Raj” Singh recently took the helm as CEO. The two have significant overlaps in their resumes, with Garner rising to the role of chief technology officer at Accolade during Singh’s tenure as leader of the healthcare platform. And Garner was a senior director at Concur, the Bellevue-based travel expense giant that Singh co-founded.

Garner shared his excitement about the new role on LinkedIn.

“From my first conversation, I could feel the drive — the hunger to innovate, the pride in craft, and the focus on building things that genuinely make a difference,” he said. “Smartsheet is redefining how AI and automation power real work, helping teams move faster, think smarter, and stay more connected than ever.”

— Baskar Sridharan, a former Amazon Web Services’ vice president of AI/machine learning services and infrastructure, is now president of Trase, an agentic AI startup that publicly launched this week.

“AI adoption is faltering within sectors that need it most: complex, highly regulated enterprises overburdened with administrative tasks that are ripe for automation,” Sridharan said on LinkedIn. “The issue isn’t innovation, it’s implementation.”

Trase has $10.5 million in pre-seed funding, and states that its “initial focus is on complex, highly regulated industries, enabling enterprises in healthcare, national security, and energy to create and deploy autonomous turn-key agents into existing infrastructure…”

Sridharan began his tech career with a nearly 16-year run at Microsoft. He was a principal engineer and architect for an Azure data storage repository that served large analytic workloads. He then moved to Google’s Kirkland, Wash., office where he was vice president of engineering for the Google Cloud platform.

Trase is based in Virginia, but Sridharan will remain in Seattle.

— Qualtrics named two new leaders. The company, co-located in Seattle and Provo, Utah, offers technology that helps businesses gather data and improve the interactions that customers, employees and others have with their products and services.

• Provo-based Mark Hammond joined the company as SVP of core AI, previously working for Microsoft in autonomous systems and technology bridging physical and virtual assets.
• Seattle-based Jeff Gelfuso was promoted to SVP and chief product experience officer. Gelfuso joined Qualtrics in January. He previously worked at Workday, Amazon, Facebook and Microsoft.

Qualtrics last month announced a $6.75 billion deal to buy Press Ganey Forsta, a company focused on managing experiences for healthcare companies.

— Seattle cybersecurity company WatchGuard Technologies named Joe Smolarski as CEO. Smolarski joined the company from security management company Kaseya, where he held the roles of president and chief operating officer. He is credited with helping lead a 10-fold revenue increase and multi-billion-dollar valuation growth for the Florida company.

Vats Srivatsan had been serving as WatchGuard’s interim CEO since May 2025, following the departure of Prakash Panjwani. Srivatsan will remain on the board of directors.

— Hubble Network, a Seattle-based space-tech startup, named two leadership hires. The news follows its September announcement of $70 million in new funding to accelerate the growth of its satellite-powered Bluetooth network.

• Damien Michau, an engineer with two decades of experience, is Hubble’s VP of engineering, joining from the software company Endor Labs.
• John Marbach, a past marketing manager, is head of growth. Marbach previously led growth marketing at the cloud company Grafana Labs.

— Mike McGee is CEO of For Effect, a new company that he’s helping launch that provides tech support for nonprofits and small businesses. “Our goal is to help organizations get the most out of their technology, implement automation, and utilize AI agents where appropriate,” McGee said on LinkedIn.

McGee was previously at Vacasa, Accolade, Concur and other Seattle-area tech companies.

— Caleb John is now a principal engineer at Pioneer Square Labs, a Seattle venture firm and startup studio. John was co-founder and CEO of Pongo, a search startup that was acquired last year by Moondream, and previously founded Cedar Robotics, a startup that built indoor delivery robots for restaurants.

— Seattle-based coaching firm Close Cohen Career Consulting announced that former Zillow VP Nancy Poznoff has joined as an executive coach. The firm, which advises senior professionals nationwide who are navigating career transitions, also shared that it has expanded into the Raleigh-Durham area.

Poznoff will remain as CEO and co-founder of Mother Bear Agency, an independent marketing and communications firm. Her past roles include marketing leadership at Starbucks and T-Mobile.

— Angelina DiPreta is a principal at Maveron, a venture capital firm started in 1998 by Starbucks CEO Howard Schultz and Seattle-based tech investor Dan Levitan. San Francisco-based DiPreta was formerly the consumer practice lead at the firm Premji Invest for nearly six years.

— Aaron Ward is co-founder and CEO of Huckleberry, a startup co-located in Portland, Ore., and New Zealand that’s developing a voice-enabled platform that allows managers, HR and teammates to share workplace performance feedback. Ward is a serial entrepreneur, previously launching AskNicely, a customer experience tech company.

— Longtime Seattle-area investor Brianna McDonald has joined the board of the Angel Capital Association Board. Earlier this year, McDonald became CEO of Ecosystem Venture Group, a new organization that blends startup investment funds with services for entrepreneurs and investors.

Rajeev “Raj” Singh has made a career out of seeing the next wave before it hits. He bet on software-as-a-service with travel expense giant Concur three decades ago. He bet on virtual care with Accolade before telehealth went mainstream.

Now, he’s betting that Smartsheet can redefine enterprise software for the AI era.

“If this transformation moment weren’t happening, I probably wouldn’t be here,” Singh said in an interview with GeekWire after his keynote at Smartsheet Engage at the Seattle Convention Center.

Singh took the stage Wednesday morning at the company’s annual conference — less than 30 days into his new role as CEO of the Bellevue-based software maker best known for helping businesses organize and track work.

Founded two decades ago, Smartsheet is one of region’s iconic tech companies, with a large customer base of major businesses and more than $1 billion in annual revenue. It went private earlier this year in a $8.4 billion deal with Vista Equity Partners and Blackstone.

Smartsheet competes in a crowded and fast-evolving market for productivity and work-management software that includes legacy players such as Microsoft, Google, and Salesforce, along with newer challengers including Asana, Monday.com, Airtable, and ClickUp.

Singh, who succeeds longtime CEO Mark Mader, framed the transition as an opportunity to challenge old perceptions of Smartsheet. He referenced enterprise buyers who still ask if it’s just an “online spreadsheet company” or a to-do list manager.

“It’s time to step out of the shadows for Smartsheet,” Singh said in his keynote speech at the conference, which runs Nov. 5-7 and attracts around 5,000 attendees.

Smartsheet on Wednesday announced new features as part of its “Intelligent Work Management” platform that combines AI agents, knowledge graphs, and automation. The update introduces tools like Smart Assist, Smart Flows, and Smart Agents to help teams create projects, manage tasks, and spot potential issues automatically. It also adds new enterprise features such as Scenario Planning and Security Score to give companies more control and visibility across their operations.

Singh described the evolution of AI in three phases: copilots as generation one, autonomous agents as generation two, and cross-system automation — the integration of multiple enterprise tech stacks — as generation three.

“That last one is really hard, and there’s only a few companies in the world that can do it,” Singh said. “We’re going to be one of those that lead the world there.”

He said Smartsheet is focused on using AI to drive business outcomes.

“Agents aren’t definitionally valuable,” Singh said. “What’s valuable is productivity. What’s valuable is revenue. What’s valuable is cost reduction. What’s valuable is quality improvement. That’s what you can charge for — AI is a tool, not a revenue model.”

Under new private equity ownership, Singh said Smartsheet has more freedom to accelerate.

“It gives us more license to do what we need to do and to go fast — which we have to do,” he said.

Asked how Smartsheet will compete against AI-driven startups tackling work productivity, Singh — who recently invested in a Seattle-area AI company — said incumbents still hold the edge “if they have courage.”

“The incumbency advantage is customers, workflows, data,” he told GeekWire. “If I have petabytes of data and you’ve got none — if you beat me by understanding my customer better than me, then I was asleep at the switch and I was supposed to lose.

“You might go faster building software, but I should go faster building insight. And if I lose, it’s because I was lazy. If I lose, it’s because I wasn’t paying attention. And I’d like to think that’s not going to be us.”