Head of Cloud Infrastructure

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What Calendly is looking for in applicants

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 Engineering team? 

We’re growing fast and looking to scale our cloud native platform capabilities to empower product development and business intelligence as we deliver solutions to our world-wide audience. We are seeking a Head of Cloud Infrastructure to help us do that by crafting and leading the expansion of our continuous delivery ecosystem on a secure and highly available, self service infrastructure. Reporting directly to the CTO and collaborating with peers in the technology organization, this role affords the opportunity to scale a strong team of SREs and data engineers on a journey to best-in-class cloud infrastructure automation.

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

  • Design, lead, develop and scale our cloud infrastructure organization in support of business needs while identifying new opportunities to drive innovation 
  • Unlock, evangelize, and optimize cloud native capabilities to drive speed to market without compromising reliability or system integrity
  • Collaborate broadly on concepts such as disaster recovery, data stewardship, and multi-region/multi-cloud strategies to prioritize the roadmap for Calendly’s cloud platform
  • Build upon modern monitoring frameworks and toolsets with dashboards, metrics, and reports to drive observability
  • Identify areas of risk, bottlenecks issues and opportunities, while advising leadership on impacts and decisions
  • Define, evangelize, and refine SRE practices and performance metrics aligned to key Calendly outcomes and business goals
  • Capacity plan to forecast infrastructure and organizational growth based historical trends and upcoming roadmap expectations 

This opportunity is for you if you have/are:

  • 15 years of experience across related infrastructure and engineering disciplines with 5 years managing teams in support of cloud-based solutions
  • Vision for enabling engineering productivity and velocity by abstracting cloud complexities and surfacing performance characteristics
  • Expertise in communicating with cross-functional Executives and teams, both in writing and orally, to deliver persuasive, holistic, unbiased, and actionable plans
  • Technical competence and the people management skills to coach team members in appropriate methodologies, communication style, and technical solutions 
  • Demonstrated success with secure data architectures and cloud infrastructure automation for highly available systems
  • Proficiency with Google Cloud Platform, Kubernetes, and distributed services architectures
  • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

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

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.

Want some tips on how to get an interview at Calendly?

What is Calendly looking for?
If this role looks interesting to you, a great first step is to understand what excites you about the team, product or mission. Take your time thinking about this and then tell the team! Get in touch and communicate that passion.
What are interviews for Head of Cloud Infrastructure like?
Interview processes vary by company, role and team. The best plan is to see what others have experienced and then plan accordingly.
How to land an interview at Head of Cloud Infrastructure?
A great first step is organizing your path to an offer. Check out Kiter for tools to get started!