HubSpot is a Tech company that provides software applications in Marketing, Sales and Support in addition to a CRM platform to small and mediums size (SMB) companies. The case describes the early days of HubSpot and provides a view into the strategies used by the founders to drive growth within the SMB segment. The company created the Inbound Marketing category and successfully used web2.0 technology to grow its customer base. The COVID years helped accelerate the company’s growth as SMBs aggressively adopted the digital platform and now with the advent of AI tools, HubSpot is again helping SMBs grow and compete in an increasingly digital world.