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EPISODE · May 13, 2026 · 27 MIN

Automating HR admin to solve a $400k mess

from The WorkOps Podcast · host by Kinfolk

SummaryWhen the sole operator of a global company’s immigration process left, a critical workflow supporting 10% of the workforce imploded. What remained was an undocumented, email-based system, causing widespread employee anxiety about work authorization and threatening the company’s ability to retain essential US-based talent. This created a strategic nightmare: a global healthcare data analytics firm, where much of its data could not be sent offshore, faced losing critical personnel due to a broken internal process.Chesney Woodall, an HR Director initially unfamiliar with immigration, inherited this mess. She quickly found herself managing 25 simultaneous immigration cases while operating as a key contributor on a three-person US HR team for a 1,000-employee company. This "messy middle" between top-down goals and bottom-up work created an accountability gap that put talent retention and business continuity at risk. To systematize the process, Chesney leaned on cross-functional collaboration and existing tools, transforming a manual, fear-inducing workflow into a more transparent system. Now, Chesney uses AI as a personal learning assistant, democratizing complex knowledge and freeing up strategic time to focus on people-centric HR.Timestamps00:10 The undocumented immigration process creating a single point of failure03:29 10% of the company's global workforce impacted by visa uncertainty04:35 "If it touches the employee, it comes to HR": Navigating process ownership06:07 The Excel spreadsheet chaos and undocumented immigration tracking07:47 Employee fear: Losing work authorization and business continuity risk09:22 How ChatGPT became Chesney's accidental immigration SME10:46 Automating admin: Unlocking strategic time for people-centric HR16:40 Building an internal operating system for immigration with Jira18:46 The manual gaps: Jira’s limitations and the need for further automation22:56 AI's role in improving employee experience and information discoverabilityTakeawaysStandardize critical processes to avoid a single point of failure, especially when they directly impact talent retention and business continuity.Utilize existing internal tools and cross-functional teams to build solutions, leveraging institutional knowledge before investing in new software.Systematize administrative tasks to free up HR for strategic initiatives like proactive talent management and improving employee experience.Connect with the guestLinkedIn: https://www.linkedin.com/in/chesney-woodall/Learn more about Cedar Gate: https://www.cedargate.com/ SponsorThis episode is brought to you by Kinfolk, the AI service desk built for HR.See more at kinfolkhq.com

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