Head of IT

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

We are the infrastructure of our business that allows us to scale to new heights. 

Why do we need you? Well, we are looking for a Head of IT to be responsible for leading all aspects of the IT function at Calendly. You will report and collaborate with the CFO. 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 need an authority and influential technology leader that has helped companies move through various stages of growth.

Includes leading a group of passionate IT professionals who oversee the IT programs of a growing and remote company. You will bounce around topics such as IT projects and system management, ensuring the IT infrastructure of the company is reliable and secure, and monitoring help desk knowledge management, and training. You will also help executives think strategically about the software we deploy across the organization.

• Coordinate and oversee IT operations at Calendly
• Enable efficient distributed work for a remote-first culture
• Design the cloud-based SaaS technology infrastructure and endpoint management solutions for an international workforce needed to fuel hypergrowth
• Well versed in SaaS application, endpoint management and security 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 Chief Information Security Officer to identify and mitigate security risks
• Evaluate business requirements for IT needs and systems and lead all aspects of 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
• Is responsible for the company IT help function for employees
• Acts a thought leader on IT trends and standard methodologies to uplevel company knowledge and expertise
• Insert day-to-day responsibilities here

• 10+ years dynamic work related experience in IT management and project governance
• Certifications and continuing education preferred (ITIL, ITSM, Agile, Lean)
• Advanced experience in leading 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 handling the development of technical solution models that satisfy identified business needs/requirements
• Strong consultative skills and demonstrable ability to achieve corporate business objectives across functional and organizational boundaries
• Experience developing and leading impactful teams
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

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.

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 [email protected]. 

Calendly is registered as an employer in many, but not all, states. If you are located in Hawaii or Alaska, you will not be eligible for employment. 

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