Creating the 'Airbnb for Offsites': Jared Kleinert on Building the Future of Work Retreats

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Recorded08 May 2025

Publisherapi.substack.com ↗

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In this episode of HR Heretics, Nolan Church and Kelli Dragovich interview Jared Kleinert, founder of Offsite.com, who shares insights on planning effective team retreats that transform from "nice-to-have" into strategic "must-have" events for remote and hybrid companies. Kleinert emphasizes that successful offsites require intentional planning with clear objectives, arguing that thoughtfully designed retreats drive organizational alignment, build trust between teammates, and provide measurable business value beyond just logistics.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH JARED, NOLAN + KELLI ON LINKEDINJared: https://www.linkedin.com/in/jaredkleinertNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—LINK/S:Offsite: https://marketplace.offsite.com/inquiry?utm=hrheretics—TIMESTAMPS:(00:00) Intro(00:47) Offsite's Business Model and Vision(02:17) Remote Work Trends and Offsite Planning(04:49) Elements of a Successful Offsite(09:38) Measuring Offsite ROI and Effectiveness(14:00) Adapting Offsites During Economic Downturns(16:26) Sponsors Planful | Metaview(19:52) Strategic Offsite Planning and Best Practices(26:46) Balancing Team Building and Business Performance(30:34) Executive Offsite Tactics and Trust Building(34:04) Pre-Offsite Preparation and Intention Setting(37:15) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

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