Senior Product Security & Security Operations Leader

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Senior Manager, Security Ops & Prod Security

Remote - US

What's in it for you?

Ready to make a serious impact? Millions of people already rely on Calendly, and we're still in the midst of exciting product growth — 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.

About the team and opportunity

Calendly takes the work out of scheduling, giving our customers more time to focus on what truly matters. Our software is trusted by millions of users worldwide, with thousands more joining us every day. To sustain our rapid growth, we're seeking top talent to help shape the future of our product and continue delivering exceptional value to our customers.

Why Join Calendly's Security Team?

Joining Calendly's Security team offers a unique opportunity to be part of a fast-growing, high-impact company that's transforming how people schedule meetings. We're committed to fostering a strong security and engineering culture that attracts self-starters who thrive in dynamic, innovative environments. If you're passionate about security and excited to explore uncharted territory, this is the place for you.

A day in the life of a Senior Manager, Product Security & Security Operations at Calendly

We are seeking a highly technical and strategic Senior Manager of Product Security & Security Operations to lead, mature, and scale both functions. This leader will build strong partnerships across Product and Engineering, embed security throughout the software development lifecycle, and strengthen Calendly's ability to detect and respond to threats.

The ideal candidate combines product and application security depth with strong security operations experience. They will lead teams, set strategy, and remain close enough to the work to guide architecture reviews, vulnerability remediation, detection engineering, investigations, and high-severity incidents.

Key Responsibilities:

  • Lead the Product Security and Security Operations teams, developing talent and holding the teams accountable for measurable outcomes.
  • Define strategy, operating plans, metrics, and resource priorities aligned with Calendly's highest risks.
  • Build strong partnerships across Security and with key cross-functional teams to align on risk, response, and remediation.
  • Communicate priorities, risk tradeoffs, and program performance to senior leadership and cross-functional stakeholders.
  • Scale product security capabilities, including threat modeling, application security testing, vulnerability management, and developer enablement.
  • Lead detection engineering, incident response, threat intelligence, monitoring, and threat hunting capabilities.
  • Guide high-severity incidents, complex investigations, and security reviews, driving durable remediation of systemic issues.
  • Establish standards for control coverage and effectiveness across applications, cloud, identity, and endpoints.
  • Manage program budgets and strategic security vendors.

What We're Looking For

This opportunity is for you if you have:

  • 7+ years of cybersecurity experience across product, application, or infrastructure security, plus security operations, incident response, or detection engineering.
  • 4+ years managing experienced security engineers or multidisciplinary technical teams.
  • Strong communication skills and the ability to navigate sensitive decisions with technical teams and senior leaders.
  • Experience defining strategy and delivering measurable outcomes across multiple security disciplines.
  • Experience building or scaling product security programs with Product and Engineering teams.
  • Strong knowledge of secure software development, threat modeling, application security testing, vulnerability management, and cloud-native architectures.
  • Strong knowledge of incident response, detection engineering, SIEM, EDR, cloud security, and identity security.
  • Experience translating ambiguous risks into prioritized, cross-functional programs and driving remediation through influence.
  • Experience managing budgets, MSSPs, testing firms, or other security providers.
  • Authorization to work in the United States, as Calendly does not provide immigration sponsorship at this time.

Tier 1 Salary Hiring Range

$265,582 - $312,450 USD

Tier 2 Salary Hiring Range

$243,451 - $286,412 USD

Tier 3 Salary Hiring Range

$221,319 - $260,375 USD

The ranges listed above 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 equity awards, and competitive benefits. Eligible Sales employees also qualify for a Sales Incentive program.

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 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

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 let your Recruiter know when first connecting with them. Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Delaware, Hawaii, Idaho, Iowa, Montana, Nebraska, North Dakota, Rhode Island, South Dakota, 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

This role may require occasional travel for company events, team collaboration, or offsites.

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Demographic questions

Calendly has an inclusive culture of belonging, where our people intentionally foster a diverse workplace where everyone is welcomed, valued, respected, and heard. Our inclusive culture engages the full potential of each individual to accelerate innovation and our ability to drive business outcomes that fulfill our mission. Your responses will be used (in aggregate only) to help us identify areas of improvement in our process. Your responses will not be associated with your specific application and will not in any way be used in the hiring decision.

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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?

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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...