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Head of Data

  • San Francisco (Hybrid)
  • Engineering

About the team & opportunity

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

We make things possible for our customers through impactful innovation.

As Head of Data, you will interact with business stakeholders across the company to understand needs and prioritize the initiatives that drive the most business and customer value. In this role, you will lead a multi-disciplinary data team to evolve the foundation of business and product intelligence for Calendly. This role leads the teams in the creation, support, and evolution of our cloud technologies underpinning a SaaS solution that supports millions of users daily. In partnership with development, product, and business partners, you own the data structures, models, and ecosystem of services that inform business strategy, improve our understanding of our customers, and enable an intelligent product experience. Your team strives for excellence in flexibility, scalability and security of Calendly’s greatest untapped asset!

A day in the life of Head of Data at Calendly

Aligned with a fast growing and data-driven organization, you will educate the company with a common understanding of our data capabilities to drive a deeper understanding of the key business metrics, trends, and underlying factors. This critical role socializes a roadmap of improvements with business leaders to implement high-quality, data-driven solutions and surface valuable, innovative insights to end users while ensuring data accuracy and consistency. In a highly collaborative environment where collegial sparring is key to the best ideas, you are encouraged to use your creativity and passion to accomplish the company’s goals.

On a typical day, you will be working on:

  • Building and leading a cross functional team that supports our data platform and machine learning mission to enhance business knowledge and opens opportunities for end user insights
  • Partnering with the Finance, Sales, Marketing, Product and CX departments to prioritize use cases, design data marts, and surface services that drive growth opportunities
  • Defining, architecting, evangelizing, and governing enterprise data flows, data model, and data standards that are critical to understanding and measuring key Calendly business drivers
  • Enabling business model evolution by defining, designing and governing the data and systems that provide user-based telemetry and online experimentation like AB testing
  • Designing, building, and evolving machine learning and artificial intelligence capabilities that will benefit internal customers and Calendly's end users
  • Anticipating future needs in people and technology to ensure the data ecosystem solves the needs of the present while growing to enable additional value creation in the future

What do we need from you?

  • 15+ years of experience immersed in data analytics, architecture, and system integrations in support of providing business and customer value
  • 7+ years of experience as a people-manager leading multi-disciplinary SaaS data initiatives
  • Keen understanding and experience aligning cross-functional executives and teams, both in writing and orally, to deliver strategic plans and business value
  • Agile, engineering competence with the people leadership skills to mentor team members in appropriate methodologies, communication style, and technical solutions needed
  • Demonstrate understanding of artificial intelligence leadership and enablement
  • Bachelor's degree in computer science or related engineering field (preference for data specializations) 
  • 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?

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 joining Calendly and growing 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 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

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

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