Skip to content
What’S It Like – 3@2X

Head of IT

  • Remote - Must be located in FL, GA, PA, SC, TX
  • Operations

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 Finance & Operations team? 

The Head of IT will have a unique opportunity to work directly for the CFO to oversee the IT function for Calendly. Our growth and transformation is supported by having the right technology foundation for growth at scale. This role will act as the source of vision and execution for cloud-based SaaS technology decisions at Calendly with an emphasis on internal systems supporting our business operation. We are looking for an experienced and influential technology leader that has helped companies move through various stages of growth

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

  • Oversee IT operations at Calendly
  • Enable efficient distributed work for a remote-first culture
  • Design the cloud-based SaaS technology infrastructure needed to fuel hypergrowth
  • Well versed in SaaS application security to include tools like Okta and Jamf
  • Experience supporting remote telephony solutions for distributed customer-facing teams
  • Implement IT strategies and infrastructure in a way that empowers functional leaders
  • Partner with the Head of Information Security to identify and eliminate security risks
  • Evaluate business requirements for IT needs and systems and oversee the process to prioritize and fulfill those needs
  • Assesses need for new technology investments and makes the case for funding approval
  • Builds out the IT team to scale according to company needs
  • Maintains relationships with outside technology vendors
  • Oversees the company IT help function for employees
  • Acts a thought leader on IT trends and best practices to uplevel company knowledge and expertise 

This opportunity is for you if you have/are:

  • 10+ years progressive work related experience in IT management and project governance
  • Bachelor’s degree in information technology, information systems, computer science or related field (graduate degree a plus)
  • Certifications and continuing education preferred (ITIL, ITSM, Agile, Lean)
  • Advanced experience in managing large, cross-functional technology implementations   
  • Sound understanding of computer systems, networks, security, telecommunications, databases and storage systems
  • Knowledge of relevant coding languages and security protocols
  • Effective verbal and written communication skills with the ability to take complex information and present to all levels of management, staff, clients and vendors.
  • Demonstrated skills in managing the development of technical solution models that satisfy identified business needs/requirements
  • Strong consultative skills and demonstrated ability to achieve corporate business objectives across functional and organizational boundaries
  • Experience developing and leading high-performing teams 
  • 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.

Join Now