Casey O'Brien is an experienced sales professional currently serving as Enterprise Account Director at MaintainX since September 2025. Prior experience includes the role of Enterprise Named Account Executive at Smartsheet from April 2022 to September 2025, where Casey led strategic enterprise customers to achieve transformational change and earned recognition in the 2024 Presidents Club. Prior to Smartsheet, Casey held various positions at Datto from February 2017 to March 2022, including Enterprise Sales Team Lead and Sr. Enterprise Account Executive, earning multiple Presidents Club honors. Earlier roles include Account Executive at IdeaPaint and Financial Advisor at New York Life Insurance Company. Casey holds a Bachelor of Science in Business Management from the University of Massachusetts Lowell, graduated in 2014.
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