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Redbord started at HubSpot working directly with its customers as he personally onboarded hundreds of businesses onto the SaaS platform. He then went on to start HubSpot's customer operations team which evolved into the HubSpot Academy.

In 2012, Redbord took over HubSpot's global customer support and success department and scaled it internationally across multiple regions. As the company went public, he joined the HubSpot executive team as the Vice President of Customer Success to oversee the end-to-end customer experience including customer support, operations, education, onboarding, implementation, upgrades and renewals. While Redbord was leading HubSpot's Customer Success team, HubSpot's overall subscription revenue grew to over $500 million ARR.

In 2017, Redbord switched roles to lead the product development of the HubSpot Service Hub, a tool built to serve professionals in customer support and success roles. Within its first year, the Service Hub delighted over 5,000 customers, and it continues to be HubSpot's fastest-growing product.