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Head of Product Engineering Platform Services

July 9, 2026

About the team & opportunity What’s so great about working on Calendly’s Engineering team? Calendly is the scheduling automation and meeting lifecycle platform used by millions of users for eliminating the back-and-forth emails to find the perfect time — and so much more. We are looking for an experienced and hands-on leader in the product development space. This is an exciting opportunity to create, drive, and evangelize a vision for Calendly’s shared services platform. In this role, you will lead a group of engineers that build critical core services depended upon by the wider product development organization. Why do we need you? Well, we are looking for an experienced Engineering leader who will bring operational maturity, technical subject-matter expertise, and the ability to empower the wider product development organization. This position reports to the Head of Infrastructure and Platform Services and is located remotely in the United States. A day in the life of a Head of Product Engineering, Platform Services at Calendly On a typical day, you will be working on: <ul> <li> Defining and executing the vision and strategy for the Platform Services organization, aligning with the Calendly’s goals and priorities </li> <li> Supporting and mentoring a team of managers and engineers, providing technical guidance and coaching on their career development </li> <li> Driving innovation and adoption of new technologies and methodologies that enhance Calendly’s services </li> <li> Ensuring the quality, performance, security, and scalability of platform services, following best practices and standards </li> <li> Collaborating with other engineering teams, product managers, and stakeholders to understand the business requirements and deliver solutions that meet or exceed expectations </li> </ul> What do we need from you? <ul> <li> 12+ years of software engineering experience, with at least 5 years in a leadership role </li> <li> Experience leading high-performance engineering teams </li> <li> Experience building highly-available distributed back-end systems </li> <li> Comfortable working as a change-agent, and drive adoption of modern engineering methodologies </li> <li> Knowledge of cloud platforms, such as GCP and their services and tools </li> <li> Strong communication, collaboration, and problem-solving skills </li> <li> Passion for delivering high-quality products and services that delight customers </li> <li> Ability to iterate and ship fast </li> <li> Past startup experience is highly preferred </li> <li> Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time </li> </ul> 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. 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 <a href="mailto:recruiting@calendly.com">recruiting@calendly.com</a> . Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Hawaii, Montana, North Dakota, South Dakota, Nebraska, Iowa, and West Virginia, you will not be eligible for employment. Note that all individual roles will specify location eligibility. All candidates can find our Candidate Privacy Statement here Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection The ranges listed below are the expected annual base salary for this role, subject to change. Calendly takes a number of factors into consideration when determining an employee’s starting salary, including relevant experience, relevant skills sets, interview performance, location/metropolitan area, and internal pay equity. Base salary is just one component of Calendly’s total rewards package. All full-time (30 hours/week) employees are also eligible for our Quarterly Corporate Bonus program (or Sales incentive), equity awards, and competitive benefits. Calendly uses the zip code of an employee’s remote work location, or the onsite building location if hybrid, to determine which metropolitan pay range we use. Current geographic zones are as follows: Tier 1: San Francisco, CA, San Jose, CA, New York City, NY Tier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D. C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA. Tier 3: All other locations not in Tier 1 or Tier 2 $57,500 — $122,500/year </code></pre>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...