Rachel Obstler

With more than 20 years of experience leading product organizations, Rachel Obstler was appointed chief product officer in 2026 to guide Contentsquare’s global product strategy. She previously served as Contentsquare’s senior vice president of product and was chief product officer at Heap, which Contentsquare acquired in 2023. Her background also includes leadership roles at PagerDuty and Dynatrace.

As chief product officer, Rachel leads product and design teams, ensuring Contentsquare’s Experience Intelligence platform evolves to meet the demands of an increasingly complex customer experience landscape. She oversees continued integration across behavioral analytics, conversational intelligence, and AI-powered automation, adapting the platform to deliver deeper insights, faster paths to action, and the capabilities customers need to stay ahead in a rapidly transforming market.