Benefits Manager

About the team & opportunity

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

We are the foundation that aims 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 Senior Benefits Manager who will bring their deep expertise in retirement and health and welfare benefits to drive the operational execution of all of Calendly's benefits and lead the benefits team. You will report to the Head of Total Rewards and will be responsible for benefits compliance, carrier management and implementation, and executing the team's communications strategy.

A day in the life of a Senior Benefits Manager at Calendly

On a typical day, you will be working on:

• Keeping Calendly's benefits compliant with all federal, state and local regulations, including ACA measurement, 1095-C filings, non-discrimination testings, state healthcare notices, and more.
• Lead the annual 401(k) audit to ensure plan compliance and accuracy.
• Responsible for the planning and execution of Calendly's annual Open Enrollment, including Workday plan configurations, communications, and working closely with the Workday team on carrier interfaces.
• Participate in regular benefits surveys so Calendly can measure the competitiveness of our benefits offerings.
• Execute all benefits communications throughout the year to help keep Cal Pals informed of their benefits offerings.
• Lead large projects and initiatives, including carrier changes and system transitions.
• Oversee all processes, policies, and projects related to leave of absences.

What do we need from you?

• 5+ years of leading retirement and health and welfare benefits at a Technology/Saas company.
• 1+ year of people leadership experience.
• Experience in Workday, including Core, Timekeeping, and Benefits SKUs.
• Deep knowledge and experience of benefits legislation, including ERISA, IRS Section 125, PPACA, HIPAA, and state/local legislation.
• Strong project management and organizational skills.
• Excellent communication skills, including written and verbal.
• Strong analytical and technical skills, including MS Excel.
• 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 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.

We aim to provide an inclusive and equitable candidate experience to everyone who expresses interest in working at Calendly. If selected, 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 recruiting@calendly.com.

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