1. One or more devices comprising: one or more processors; and a memory having computer-executable instructions stored thereupon which, when executed by the one or more processors, cause the one or more devices to: observe, for a client organization and as part of an onboarding engagement session, a current environment of client-managed computing infrastructure that hosts a service; receive client input defining expectations for a target environment of the service, where implementation of the target environment of the service requires onboarding of at least part of the service from the client-managed computing infrastructure to network computing infrastructure; access a database of onboarding information to identify a set of tasks to move the client organization from the current environment to the target environment; generate, based at least in part on the onboarding information, a state diagram that models dependencies between individual tasks in the set of tasks; calculate, within the state diagram, a task execution path associated with a highest probability of success for moving the client organization from the current environment to the target environment; identify, from the set of tasks, a first subset of tasks along the task execution path; provide, to the client as part of a deployment plan, the first subset of tasks; continuously monitor a status of an individual task in the first subset of tasks; determine that the individual task has not been completed within an expected amount of time to complete the individual task; re-calculate, based at least in part on the determination that the individual task has not been completed within the expected amount of time to complete the individual task, the task execution path; identify, from the set of tasks, a second subset of tasks along the re-calculated task execution path; and provide, to the client as part of an updated deployment plan, the second subset of tasks to be implemented prior to the implementation of the individual task.