Smartsheet Names Drew Garner as Its First Chief AI Officer

Bellevue, Washington-based work management software company Smartsheet has named Drew Garner as its first Chief AI Officer, adding a new executive role as enterprise software companies expand AI deployment across operational workflows. The company announced the appointment in a LinkedIn post on May 21. Garner, who joined Smartsheet as Vice President of Engineering in November 2025, said the mission behind the role would remain focused on practical workplace outcomes. “AI that earns its keep with the people doing real work,” Garner wrote in a separate LinkedIn post. Garner previously worked with Smartsheet CEO Rajeev “Raj” Singh at healthcare technology company Accolade, where Garner later became CTO during Singh’s tenure as CEO. Both executives also previously held leadership roles at travel and expense software company SAP Concur. The appointment comes during a broader leadership transition at Smartsheet following Singh’s arrival as CEO in late 2025. In an interview with GeekWire last year, Singh said the company needed to “step out of the shadows” as AI reshapes enterprise software. Enterprise Software Firms Formalize AI Leadership Smartsheet’s creation of a Chief AI Officer role reflects a broader shift across enterprise software and operational technology companies as AI initiatives move from experimentation into executive oversight. Companies across healthcare, HR, and enterprise operations have increasingly added dedicated AI leadership positions tied to deployment, governance, and workforce integration. Recent examples include Businessolver appointing Sony SungChu as its first Chief AI Officer and SCAN naming Aman Bhandari Chief AI Officer to scale AI across operations. Unlike several high-profile AI executive hires centered on research or public-facing AI products, Smartsheet promoted Garner internally from its engineering organization. Garner’s background has focused on enterprise infrastructure, operational scaling, and customer-facing product systems rather than frontier AI model development. The company framed the role around customer workflows and operational productivity instead of standalone AI tooling. In its announcement, Smartsheet said Garner would work directly with customers to ensure AI systems are tailored to how teams operate and “accelerating real outcomes.” AI Becomes Embedded Inside Workflow Platforms Smartsheet has already integrated generative AI capabilities into its platform before formally creating the Chief AI Officer position. The company currently offers AI-assisted formula generation, text summarization, workflow recommendations, and spreadsheet analysis tools inside its work management software, according to its product documentation and AI feature pages. The strategy mirrors a wider shift across enterprise software companies as vendors move AI from standalone chatbot interfaces into workflow execution systems. Enterprise software providers are increasingly redesigning operational workflows around AI-native systems rather than limiting AI to productivity add-ons. Smartsheet competes in the enterprise work management market alongside companies including Asana, Monday.com, Atlassian, Notion, and Airtable, many of which have introduced AI assistants and workflow automation features during the past two years. Smartsheet has positioned its AI strategy around operational integration and responsible deployment. In a recent LinkedIn post, the company described 2026 as the point where enterprise AI adoption was moving beyond experimentation into production workflows.

Smartsheet Names Drew Garner as Its First Chief AI Officer

Enterprise Software Firms Formalize AI Leadership

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