Drimva

Calendly

Staff Product Manager, AI Assistant

$237K–$300K

San Francisco (Hybrid) +1 · Staff · Full-time · Posted Aug 19, 2026

Location
San Francisco (Hybrid)
San Francisco, California, United States
Experience
Minimum of 8–10 years of varied PM experience across startups and scaled companies.
Visa sponsorship
Must be authorized to work lawfully in the United States; Calendly does not engage in immigration sponsorship.

About the job

Owns Calendly’s AI assistant that helps professionals prepare for meetings, follow up, and take next steps by surfacing and drafting actions users can trust.

What you'll do

  • Identify meeting-related user problems and turn them into simple assistant experiences.
  • Build trust in assistant outputs so users can gradually delegate more actions.
  • Ship versions to users, observe responses, and iterate quickly.

What they ask for

  • 8–10 years of varied product management experience across startups and scaled companies.
  • Experience building 0-to-1 products.
  • Ability to work in the San Francisco office 2 times per week.
  • Authorized to work lawfully in the United States; Calendly does not provide immigration sponsorship.

Nice to have

  • Experience with assistant or agent products, or AI-generated content where voice and tone mattered.
  • Founder experience.

Pay

$237,305 — $300,121 USD annual base salary

AI focus

Own an AI assistant that surfaces and drafts meeting preparation, follow-up, and next-step actions; improve output quality and earn user trust to enable greater autonomy.

Model-written summary · the original posting is authoritative

First seen Oct 27, 2026 · Last verified Nov 5, 2026 (UTC)