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CalendlyCalendly

Staff Product Manager, Intelligent Customer Experience

Leads the strategy and roadmap for Calendly’s intelligent customer experience, improving AI-powered support, automated resolution, escalation, and measurement. Requires 10+ years of product management experience, direct conversational-agent expertise, and the ability to drive adoption across teams without direct authority.

About the job

Responsibilities

  • Own the strategy, roadmap, and outcomes for intelligent customer experience, including AI support quality, automated resolution, and human escalation.
  • Increase automated resolution by enabling support agents to answer customer questions and take actions accurately while routing complex issues to human support.
  • Define and improve AI quality metrics, including answer accuracy, resolution quality, escalation effectiveness, and failure modes.
  • Build measurement and observability for agent and bot quality, automated resolution rate, customer experience cycle time, escalation routing, and customer satisfaction.
  • Establish and drive adoption of a company-wide supportability contract so new capabilities are supportable by AI agents, automation, or human support.
  • Translate recurring bugs, product gaps, customer issues, and support insights into prioritized product and engineering work.
  • Lead cross-functional work across Product, Engineering, AI/Data, Growth, Monetization, Trust & Safety, Support, and Content Operations.
  • Use customer feedback, support data, and experimentation to prioritize investments and measure customer and business outcomes.

Requirements

  • 10+ years of product management experience across startups and scaled companies.
  • Experience building 0-to-1 platforms or capabilities adopted by internal teams.
  • Direct experience with AI-powered or conversational agents, including understanding their failure modes and answer-quality drivers.
  • Experience driving cross-functional standards or platform adoption without direct authority.
  • Strong product judgment grounded in support or customer experience data.
  • Ability to define metrics from messy or incomplete data.
  • Experience partnering simultaneously with go-to-market and R&D stakeholders.
  • Experience in B2C and/or B2B SaaS, preferably in a product-led-growth environment.
  • Must reside in California and be able to commute to the San Francisco Bay Area office.
  • Authorized to work in the United States without immigration sponsorship.

Compensation

  • Annual base salary depends on geographic tier:
    • Tier 1: $237,305–$300,121 USD
    • Tier 2: $217,530–$275,111 USD
    • Tier 3: salary range not fully provided in the posting.
  • Full-time employees are eligible for a bonus program, equity awards, and benefits.

Skills

Product Management, Artificial Intelligence, Conversational Agents, Customer Experience, Support Automation, Product Roadmap, Metrics, Observability, Experimentation, SaaS, Customer Support, Cross-Functional Leadership

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