Benefits Analyst – Remote

Remote, United States of America
Job Type


What’s so great about working on Calendly’s People team?

We are the foundation that strives to set up our people for success to do the best work of their life at Calendly.

Why do we need you? Well, we are looking for a Benefits Analyst who will bring strong communication skills and expertise in progressive benefits, leaves, and perks. You will report to the Head of Total Rewards and will be responsible for the administration and communication of our benefits, perks, leaves, and recognition programs.

On a typical day, you will be working on:

  • The administration of global employee benefit programs, including medical, dental, vision, flexible spending, disability and retirement plans
  • Benefits communications to ensure employee awareness, education and understanding (including written communications, 1:1 meetings, and presentations)
  • Leaves of absence program (including disability, FMLA, parental leave) in collaboration with our providers
  • Developing relationships with our external benefits providers to ensure high quality and compelling offerings and service
  • Analyzing program fit and making recommendations for improvements
  • Applying knowledge of laws and regulations to ensure company compliance of benefits and leave programs

What do we need from you?

  • 5 plus years of broad and dynamic benefits/total rewards experience in a Technology/SaaS company
  • A solid understanding of legislation and compliance items related to benefits and leave administration
  • Strong analytical and technical skills in MS Excel or other related software
  • Excellent communication and interpersonal skills
  • Experience with project management with regard to evaluation and implementation of benefit programs
  • A self-starter mentality with a roll-up-your-sleeves-and-get-things-done mindset
  • 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

We aim to provide an inclusive and equitable experience to everyone who expresses interest in working at Calendly. The recruiter assigned to this role will keep you informed every step of the way. Have questions? Let your recruiter know! Want to share your experience? We are passionately committed to improving and building on our process, and we consider feedback a gift.

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 

This specific role is not eligible for employment in California, Hawaii, or Alaska. Note that all individual roles will specify location eligibility.

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



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