How to Run a 4,500-Location Enterprise Rollout (In One Year) | Zach Larabee (Sr. Manager at Toast)

In this episode, I sit down with Zach Larabee, Sr. Manager of the Enterprise Sales Coordinator Team at Toast, to break down what actually happens after an enterprise deal signs, how large brands get rolled out across hundreds (or thousands) of franchise locations, and why implementations stall when expectations aren’t set upfront.Zach explains why franchisee autonomy is the #1 variable that slows rollouts, what sellers should uncover before closing (tech stack, decision rights, and standardization), and how to create urgency with operators who don’t want to be told what to do. We also get into how he won Toast’s Employee of the Year in 2020 by taking initiative during COVID, documenting the process end-to-end, making downstream teams’ lives easier, and building cross-functional trust.TOPICS WE COVERWhat Enterprise Sales Coordinators do at Toast (the “hybrid” of onboarding + sales)How rollouts work when you’re dealing with corporate and individual franchiseesThe #1 factor that determines rollout speed: franchisee autonomy vs corporate standardizationWhy rollouts get delayed at scale (1,000 locations = 1,000 different conversations)The best-case scenario: the “standard package” rollout (100 locations in a month)What’s often missing at handoff, and what sellers should ask before closingWhy identifying the customer’s tech stack early prevents onboarding surprisesWho really derails rollouts (and why it’s usually franchisees, not finance/IT)How to create urgency and excitement so owners don’t “stick their feet in the mud”Messaging that makes rollouts smoother: finding the operator’s “why” (money, experience, autonomy)Handling competitors who try to undercut pricing, and why corporate alignment mattersHow Zach won Employee of the Year: initiative, process documentation, and helping downstream teamsABOUT THE GUEST Zach Larabee is the Senior Manager of the Enterprise Sales Coordinator Team at Toast, where he leads a team that manages large-scale enterprise and mid-market rollouts across franchise brands. He’s been at Toast for 9 years, helped scale the rollout motion from the early days, and won Toast’s Employee of the Year in 2020 for his initiative and cross-functional impact during COVID.Connect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Toast: https://pos.toasttab.com/