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Staff Product Manager, Intelligent Customer Experience

Calendly· Product
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Remote$197.8k - $300.1kfull-timePosted 1mo ago

About the role

Technical Staff Product Manager responsible for the end-to-end strategy and delivery of Calendly's intelligent customer experience, including AI support, automated resolution, and human escalation. Collaborates across Product, GTM, Marketing, Support, and multiple engineering squads to create a durable, multi-quarter capability that improves customer satisfaction and growth.

Responsibilities

  • 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

Qualifications

  • 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 startups and scaled companies, including time spent building 0-to-1 platforms or capabilities that other internal teams adopted
  • Direct experience with AI-powered agents and/or conversational agents, with deep understanding of failure modes and improvements to answer quality
  • Track record of driving cross-functional standards or platform adoption across teams without direct management authority
  • Strong product sense grounded in support and/or customer experience data, comfortable defining metrics from messy or incomplete data
  • Ability to build a bold, inspirational vision for the organization and motivate teams
  • Experience partnering with GTM (support, success, content) and R&D stakeholders in B2C/B2B SaaS or product-led-growth environments
  • Authorized to work in the United States (Calendly does not sponsor immigration)

Skills

Required:AI-powered agent experienceStrategy and roadmappingCross-functional leadership without direct authority

Benefits

  • Equity awards are available for all full-time employees
  • Competitive benefits
  • Sales Incentive program for eligible Sales employees
Last updated Sep 16, 2026. Interested? Apply on the company site.

About Calendly

Free Online Appointment Scheduling Software | Calendly

Calendly is the modern scheduling platform that makes “finding time” a breeze. When connecting is easy, your teams can get more done.

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