Sr. Director Product - Workforce Intelligence - AI Transformation
Redmond, Washington, United States
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Summary
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Senior
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Top School
Chetna Gupta is a product and technology leader with 13+ years of experience building and scaling greenfield products across e-commerce, health & wellness, AI/voice, cloud, and payments at companies like Amazon, Fiserv, and Albertsons. Currently Sr. Director leading Workforce Intelligence and AI Transformation, she has a track record of shipping industry-first, award-winning solutions such as Sincerely Health and driving global delivery. She thrives in high-ambiguity environments, turning fuzzy customer needs into test-and-learn experiments that produce measurable business impact. Known for connecting stakeholders, technology, and strategy, she balances a “fail fast, learn fast” mindset with deep customer empathy to build both products and scalable processes. Her background spans hands-on technical program management at AWS and Alexa to product leadership in personalization and digital health, giving her fluency across engineering, data, and go-to-market. Based in Redmond with an MBA in entrepreneurship, she combines startup-style experimentation with enterprise-scale execution.
13 years of coding experience
17 years of employment as a software developer
MBA Entrepreneurship/Entrepreneurial Studies, MBA Entrepreneurship/Entrepreneurial Studies at Naveen Jindal School of Management, UT Dallas
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Chetna Gupta - Sr. Director Product - Workforce Intelligence - AI Transformation