Smartsheet Gets Its First Chief AI Officer: Drew Garner

Garner brings nearly a decade of enterprise technology leadership, including Accolade’s $500 million transformation and its subsequent acquisition by Transcarent.

Smartsheet has appointed Drew Garner as its first Chief AI Officer, creating a dedicated executive role for artificial intelligence leadership at the company. Smartsheet announced the appointment via LinkedIn.

Garner announced the update via LinkedIn, stating that AI should strengthen human expertise rather than render it obsolete. In his new role, he will work directly with customers to ensure Smartsheet’s AI capabilities empower teams to do real work, tailored to how they already operate.

Garner joined Smartsheet in November 2025 as Senior Vice President of Engineering, based in Seattle, where he focused on building AI and automation features. The Chief AI Officer appointment follows seven months into that tenure.

He brings a substantial track record in enterprise technology leadership. Garner spent nine and a half years at Accolade, Inc., serving as Senior Vice President of Product Development before stepping up to Chief Technology Officer in June 2021, a role he held until July 2025.

As CTO, he led Accolade’s transformation from a healthcare advocacy company into a $500 million personalized healthcare platform serving 25 million members, culminating in the company’s acquisition by Transcarent. Across his career, he has built billion-dollar technology platforms reaching over 100 million users.

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