Staff Product Manager, AI Assistant

Posted 28 Days Ago
Be an Early Applicant
San Francisco, CA, USA
In-Office
237K-300K Annually
Expert/Leader
HR Tech • Software
The Role
Own Calendly’s user engagement strategy across in-product and email experiences. Build ranking, timing, and trigger systems that encourage users to return while protecting brand trust. Lead ML-powered personalization and experimentation informed by qualitative user insights, balancing company objectives with user needs. Ship quickly, learn from real usage, and drive sustainable long-term growth. This hybrid role requires working from the San Francisco office one to three times weekly and may involve occasional travel.
Summary Generated by Built In
What’s in it for you? 

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

*This is a hybrid position located in the Bay Area; the expectation is to go into the San Francisco office 2 times per week.

Calendly is used by more than 20 million people to take the work out of scheduling.

We're now building the layer that does the work around the meeting too: the prep before it, the follow-up after it, and the next step a professional would otherwise do manually. This role owns the assistant that surfaces and drafts those actions, and the quality that makes people trust them.

What you'll do

  • Understand the work that surrounds meetings for our users: what they're trying to accomplish, where they lose time, and which of those problems are worth solving and how to solve them simply enough that users feel the help without the overhead.
  • Turn those problems into an assistant that helps at the right moments
  • Earn enough trust in the assistant's output that users are willing to hand it more autonomy over time, letting it act without reviewing every step.
  • Ship fast and learn in the open: get real versions in front of users, watch how they respond, and iterate quickly.

What we're looking for

  • A minimum of 8-10 years of varied PM experience across both startups and scaled companies; bonus points if you've been a founder
  • Experience with assistant or agent products, or with AI-generated content where voice and tone mattered
  • Real taste for AI output quality
  • Keen product sense and UX design experience, with deep empathy for customers and a drive to build delightful, frictionless experiences
  • Experience building 0-to-1 products
  • The ability to work in our San Francisco office 2 times per week
  • Authorized to work lawfully in the United States of America, as Calendly does not engage in immigration sponsorship at this time
Tier 1 Salary Hiring Range
$237,305$300,121 USD

The ranges listed above are the expected annual base salary for this role, subject to change.

Calendly takes a number of factors into consideration when determining an employee’s starting salary, including relevant experience, relevant skills sets, interview performance, location/metropolitan area, and internal pay equity.

Base salary is just one component of Calendly’s total rewards package. All full-time (30 hours/week) employees are also eligible for equity awards, and competitive benefits. Eligible Sales employees also qualify for a Sales Incentive program.

Calendly uses the zip code of an employee’s remote work location, or the onsite building location if hybrid, to determine which metropolitan pay range we use. Current geographic zones are as follows:

  • Tier 1: San Francisco, CA, San Jose, CA, New York City, NY
  • Tier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA.
  • Tier 3: All other locations not in Tier 1 or Tier 2

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please let your Recruiter know when first connecting with them. Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Delaware, Hawaii, Idaho, Iowa, Montana, Nebraska, North Dakota, Rhode Island, South Dakota, and West Virginia, you will not be eligible for employment. Note that all individual roles will specify location eligibility.

All candidates can find our Candidate Privacy Statement here

Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection

This role may require occasional travel for company events, team collaboration, or offsites.

Skills Required

  • 8-10+ years of product management experience, including senior or staff-level engagement, growth, or lifecycle ownership
  • Experience using machine learning for ranking or personalization
  • Ability to work in the San Francisco office 1-3 times per week
  • Authorized to work lawfully in the United States without immigration sponsorship
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The Company
HQ: Atlanta, GA
414 Employees
Year Founded: 2013

What We Do

At Calendly, we are excited about changing the way the world schedules. We are a profitable company, offering ample opportunities to accelerate your career. We’re obsessed with providing an elegant, delightful experience for our customers. This shapes how we develop, design, market and support. We work hard, move fast and pitch in across departments—and always make time to celebrate our accomplishments. Join a diverse workforce, leading the way in scheduling automation. Calendly, a powerful yet simple automated scheduling tool, takes the work out of connecting with others so you can accomplish more. Millions of users benefit from an enjoyable scheduling experience, more time to spend on top priorities and flexibility to accommodate individual users and large teams alike. Calendly works with Google, Office 365 and Outlook calendars and apps like Salesforce, Stripe, PayPal, Google Analytics, GoToMeeting and Zapier for a seamless user experience.

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