A day in the life of a Staff Product Manager at Calendly

This technical product management position will report to the Head of Engineering, Growth and Customer foundations team. We strive to design a seamless product experience that delights our customers. In 2026, Calendly chartered a company-wide initiative to focus on delivering Great Customer Experience -spanning our Help Center, AI support bot, Automated issue resolution, human support escalations and support engineering. We're hiring a technical Staff Product Manager to work across Product, Go to Market (GTM) stakeholders, marketing, customer support and multiple engineering squads to address real gaps in taxonomy, measurement, and process. This product manager will own the roadmap end-to-end and turn a set of disconnected efforts into a durable, multi-quarter capability that will drive defined growth, product/business outcomes, and customer satisfaction goals.

 On a typical day, you will be working on

• 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

What do we need from you?

• 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 both startups and scaled companies, including time spent building 0-to-1 platforms or capabilities that other internal teams had to adopt
• Direct experience with AI-powered agents and/or conversational agents. You have relevant experience and deeply understand where these systems actually fail and what moves answer quality, not just the pitch
• A track record of driving cross-functional standards or platform adoption across teams you don't manage — this role has real influence-without-authority demands from day one
• Strong product sense grounded in support and/or Customer experience data. Comfortable defining metrics from messy or incomplete data rather than waiting for a clean dashboard.
• Ability to build a bold and ambitious vision for the organization with ability to inspire teams to achieve a bold mission
• Experience partnering with GTM (support, success, content) and R&D stakeholders simultaneously, ideally in a Business to Customer (B2C) and/or Business to Business (B2B) Software as a Service (SaaS), product-led-growth environment
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

What’s in it for you?

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a phenomenal 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 career.

Our Hiring Process:

Typically, individuals will participate in the following interview process. However, there may be slight nuances given the role and or department we are hiring for. Please keep in mind that individuals can be declined from the position at any stage of the process.

• Qualified individuals will be invited to schedule a phone interview with a member of our recruiting team. This is a great time to ask any initial questions you have about the company or the role.
• Next, we’ll put you in direct contact with your potential manager. You’ll get a chance to learn even more about life at Calendly, the responsibilities within your role, and the qualities needed to succeed here.
• Then, you will perform an interview exercise, where you can highlight your skills.
• Next, or in parallel, you’ll meet with your potential team members.
• Finally, we connect with those you’ve worked with before, to learn more about the impact you can make, the value you bring, and the best way to set you up for success at Calendly.