Staff Product Manager at Calendly

This technical product management position will report to the Head of Engineering, Growth and Customer foundations team. We strive to design a seamless product experience that delights our customers. In 2026, Calendly chartered a company-wide initiative to focus on delivering Great Customer Experience—spanning our Help Center, AI support bot, Automated issue resolution, human support escalations, and support engineering.

On a typical day, you will be working on

• Own the strategy, roadmap, and outcomes for Calendly’s intelligent customer experience, spanning AI support quality, automated resolution, and human escalation
• Increase automated resolution by enabling the Support Agent to accurately answer questions and take actions on behalf of customers, while reserving human support for high-value and complex issues
• Define and improve AI quality, including answer accuracy, resolution quality, escalation effectiveness, and the failure modes that prevent customers from getting the right outcome
• Build the measurement and observability layer for Agent/Bot Quality Score, automated resolution rate, customer experience cycle time, escalation routing, and customer satisfaction
• Establish and drive adoption of a company-wide “supportability contract” so every new Calendly capability is supportable by AI agents, automation, or human support from day one
• Close the loop between customer issues and R&D, ensuring recurring bugs, product gaps, and support insights translate into prioritized product and engineering actions.
• Lead across Product, Engineering, AI/Data, Growth, Monetization, Trust & Safety, Support, and Content Operations to turn fragmented customer-support efforts into a durable, scalable company capability
• Use customer feedback, support data, and experimentation to continuously improve the experience, prioritize investments, and measure progress against clear customer and business outcomes

What do we need from you?

• This hybrid opportunity is open exclusively to candidates currently residing in California who can commute to our San Francisco Bay Area office
• A minimum of 10+ years of varied PM experience across both startups and scaled companies, including time spent building 0-to-1 platforms or capabilities that other internal teams had to adopt
• Direct experience with AI-powered agents and/or conversational agents. You have relevant experience and deeply understand where these systems actually fail and what moves answer quality, not just the pitch
• A track record of driving cross-functional standards or platform adoption across teams you don’t manage — this role has real influence-without-authority demands from day one
• Strong product sense grounded in support and/or Customer experience data. Comfortable defining metrics from messy or incomplete data rather than waiting for a clean dashboard.
• Ability to build a bold and ambitious vision for the organization with the ability to inspire teams to achieve a bold mission
• Experience partnering with GTM (support, success, content) and R&D stakeholders simultaneously, ideally in a Business to Customer (B2C) and/or Business to Business (B2B) Software as a Service (SaaS), product-led-growth environment
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time