On-body analyte monitoring devices configured for uncompressed and compressed configurations and methods of using the analyte monitoring devices are disclosed. The devices comprise a collapsible housing, wherein upon desired placement and user application of force to the housing converts the analyte monitoring device from an uncompressed configuration to a low-profile compressed state while guiding an analyte sensor through the skin and into contact with bodily fluid to measure and analyte level therein. Also provided are systems and kits.