Win Cutrer

Technical Support

Win Cutrer is a technical support professional with extensive experience in troubleshooting and customer advocacy within the technology sector. Currently serving as Technical Support at Assembled since July 2025, Win focuses on resolving complex issues related to scheduling, integrations, and workforce management while collaborating with engineering and product teams to enhance user experiences. Prior roles include Technical Solutions Manager and Associate Technical Solutions Manager at Headspace, where Win managed escalated technical issues and contributed to system deployments and product feedback processes. Earlier experience includes positions at Ginger as a Support Specialist and at LendingClub as a Member Support Representative, demonstrating a consistent track record of delivering high-quality support and improving operational efficiencies. Win holds a Certificate of Completion in Product Design from Designlab.

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