Calendly Staff Product Manager, AI Assistant at Calendly owns engagement systems that bring users back daily without eroding trust. This role manages ranking, timing, and triggers across product surfaces and email to build user habits.
Responsibilities
Build engagement as a system, not a pile of one-off campaigns: the ranking, the timing, the triggers that compound into a habit
Own the surfaces where Calendly shows users their next step, in-product and over email, and the craft of getting the right thing in front of the right person at the right moment.
Build the habit of returning without ever making the product feel noisy.
Ship fast and learn on real usage
Qualification
8-10+ years in productAggressive and tasteful at onceBalance user and company goals
Required
8-10+ years in product, including senior or staff-level engagement, growth, or lifecycle ownership.
Experience using ML for ranking or personalization
You let a qualitative read of user needs guide where you experiment, rather than testing at random and hoping.
You optimize for long-term growth and brand trust over small experimentation wins, and you can point to a time you passed on an easy lift because it would have cost trust.
Aggressive and tasteful at once: you push hard on engagement and know exactly where the line is.
You balance user and company goals rather than trading one for the other.
The ability to work in our San Francisco office 1-3 times per week.
Authorized to work lawfully in the United States of America, as Calendly does not engage in immigration sponsorship at this time.
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 contact us at recruiting@calendly.com. Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Alabama, Delaware, Hawaii, Idaho, Montana, North Dakota, South Dakota, Nebraska, Iowa, West Virginia, and Rhode Island, 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
The ranges listed below are the expected annual base salary for this role, subject to change.
Preferred
Qualitative read of user needs guides experimentation
Optimize for long-term growth and brand trust over small experimentation wins
Aggressive and tasteful at once in pushing engagement
