Product Manager, Products

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 expanding from a scheduling tool into a multi-product platform powered by AI. We are hiring a Staff Product Manager, New Products to lead 0→1 innovation, focusing on creating new product experiences that transform how solopreneurs and small businesses run and grow their business.

This is a highly entrepreneurial, high-visibility, high-autonomy role for a PM who thrives in ambiguous spaces, partners well with leadership, and loves building new product lines from scratch.

We design seamless product experiences that delight our customers. Calendly takes the work out of scheduling so our customers have more time to focus on what matters most. Millions of people worldwide use our software every day — with thousands more signing up daily.

As a Staff Product Manager, New Products, you'll have the rare opportunity to shape the future of Calendly's multi-product strategy. This role is focused on incubating and validating new 0-to-1 product ideas, with many of these ideas leveraging the power of AI. You'll explore bold concepts, test hypotheses quickly, and partner closely with engineering and design to bring new solutions to life.

• Extend Calendly's value beyond scheduling into new product lines powered by AI
• Drive retention, and new revenue
• Deliver net-new value that delights solopreneurs and small businesses
• Leverage AI to create experiences that feel intelligent, proactive, and effortless

You will own discovery, strategy, launch, and lifecycle ownership — including defining and delivering the success metrics for activation, adoption, revenue expansion, and customer satisfaction.

This position reports to our Chief Product Officer. You'll thrive in an environment where creativity and experimentation are encouraged, and where speed matters as much as precision.

• Lead discovery and validation of new product ideas, including rapid prototyping and customer testing
• Explore how AI can power new experiences across scheduling, meetings and beyond
• Collaborate with R&D (Engineering, Design, Research) to build MVPs and experiments that unlock high-potential opportunities
• Partner with leadership to align new initiatives with Calendly's long-term multi-product vision
• Define success metrics and run experiments to quickly evaluate product-market fit

• Define entirely new product experiences
• Build rapid prototypes and Minimum Delightful Products
• Validate problems, define user segments, and drive upgrades
• Create the product narrative, roadmap, and long-term strategy
• Own the execution path from concept → beta → GA → scale
• Influence the future of Calendly’s evolution

This is not optimization work — this is category creation.

• LLM-powered contextual reasoning (OpenAI + future models)
• Evaluation frameworks to measure AI quality, accuracy, and reliability across features
• AI tools for prototyping to rapidly iterate on UI designs
• Agentic tasks and workflows
• AI-assisted generation, summarization, and relationship insights

• CPO — product vision and multi-product strategy
• Director of AI Products — AI platform, vision, and product alignment
• XFN:
  Engineering, ML/AI, Design, Data Science, GTM, Support

• 8–10 years of PM experience across startups and scaled companies; bonus points if you've been a founder or early employee at a SaaS company
• Track record of building 0-to-1…