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Senior Manager, People Operations

  • Remote
  • People

What is Calendly?

Calendly takes the work out of scheduling so our customers have more time to work on what’s really important. Our software is used by millions of people worldwide—with thousands more signing up every day. To maintain this exciting growth, we’re looking for top talent to join our team and help shape the future of our product. 

Why join Calendly’s People team? 

The Senior Manager, People Operations will have a unique opportunity to build and manage the key processes that support our people while working directly with Calendly’s Head of People Operations. Our benefits and programs are quickly establishing Calendly as a top destination for talent in the software industry, and we never stop looking for ways to enrich our employees’ lives even further. 

We know we wouldn’t be where we are—or make it to where we’re going—without our people. And when it comes to walking the talk, we think actions speak louder than words. Our people are shown appreciation through a formal rewards and recognition program, a competitive benefits package, and countless quality-of-life perks such as our home office stipend and an annual vacation stipend. If you’re seeking an opportunity to make your mark and be part of a groundbreaking team, then this is the job for you.

What are some of the high impact opportunities you’ll tackle? 

  • Design and execute efficient and delightful people processes for critical moments like orientation, leaves, job changes and departures
  • Redesign and put in place a remote-first onboarding workflow and delivery in partnership with our Engagement team
  • Build compliance requirements and auditability into all our key processes
  • Bring to life team member self-service and a scalable (to 1,000+) support model that truly “starts with human”
  • Manage People Operations with a data-driven approach - leverage data to drive improvements in processes, team member content, and support
  • Design and create a variety of engaging resources ranging from online materials to basic procedures. Tailor existing policies and procedures to meet business specific needs
  • Continuously improve team member handbook and policies to support individual and organizational needs while maintaining compliance with all relevant requirements
  • Ensure ongoing compliance with relevant regulations and requirements to minimize risk and exposure to the company; manage compliance filings (e.g., EEO-1, VETS, AAP)
  • Coach and develop People Ops coordinators
  • Act as a strategic business partner to the People and functional leadership, as well as a hands-on generalist for the company for all things people-related
  • Proactively address emerging workplace and team member issues individually with thoughtfulness about broader implications and sustainability of solutions
  • Analyze data and offer insight into company and team-specific programs and policies and recommend data-driven solutions to achieve team goals and objectives

This opportunity is for you if you have/are:

  • 8 plus years of broad and progressive HR experience in a Technology/SaaS company, with experience leading and developing others
  • Creative at finding interim and long-term solutions and flexing to meet business needs
  • Able to work independently but skilled at cross-functional collaboration to yield best business outcomes
  • Strong HR functional expertise; knowledgeable on employment law matters, immigration, and compliance & policy management
  • A curiosity about your craft that leads you to continually seek out best practices from your peers and professional network
  • A genuine belief that CX (surprise and delight!) applies to employees too
  • Comfortable doing the nitty gritty work yourself, willing to roll up your sleeves to get things done, and able to operate in the sky or in the weeds as needed
  • A strong communicator, both written and verbal
  • The ability to juggle multiple projects at once and prioritize competing interests
  • A self-starter and proactive. You drive projects to closure without steamrolling others
  • Enthusiasm and passion for quality and attention to detail (you always do that triple check of your work!)
  • Experience working with multiple SAAS systems, e.g. Greenhouse, Ultipro, Zendesk, Workday, Lessonly, etc.
  • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Calendly is registered as an employer in many, but not all, states. If you are not located in or able to work from a state where Calendly is registered, you will not be eligible for employment.


Not the right time to come onboard?

No problem! We’re all about making connections that make great things happen, so if the time’s not quite right for you to join us, but you’re keen to stay in the loop, just register your details, and we’ll add you to our talent pool.

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