Senior Director, Product Operations

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 & Opportunity

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 hundreds 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.

At Calendly, our Product team is the engine that drives innovation and delivers impactful solutions for our customers. We’re passionate about solving real problems and enabling possibilities. As the Senior Director of Product Operations, you will play a critical leadership role overseeing operations across our product portfolio. You will drive operational efficiency, support strategic planning, and work closely with cross-functional teams to bring our product vision to life.

A day in the life: Senior Director, Product Operations 

As the Senior Director of Product Operations, you will be responsible for optimizing how our product development teams work and scaling processes to support Calendly’s growth. Key responsibilities include:

Operational Efficiency & Product Lifecycle Management

• Design, implement, and optimize processes for strategic planning and product development
• Oversee product release processes, ensuring timely and successful launches.
• Drive accountability and predictability, manage dependencies, and reduce friction across the product development lifecycle.
• Select, implement, and manage project management and communication tools used by Product development teams.
• Work with embedded team members to maintain accurate and up-to-date product documentation, including strategy documents, roadmaps, PRDs, and JIRA.

Cross-Functional Collaboration

• Serve as a key partner to Product, Engineering, Design, Marketing, and Finance departments to create and maintain clarity and drive positive outcomes for the business
• Establish and maintain clear documentation and communication channels to ensure alignment and transparency

Performance Monitoring

• Define, track, and assess key performance indicators (KPIs) for performance and operational efficiency.
• Create accountability and clarity for product-specific KPIs and ensure teams have the data inputs they need for strategic decisions and continuous product improvements. 

Strategic Support & Resource Management

• Collaborate with R&D leadership and the Executive Team to support strategic planning and investment decisions across the product portfolio
• Ensure priorities are clear and aligned within squads, across R&D, and at the company level. 
• Provide insights and recommendations based on operational data.
• Manage operational resources, including budgets and personnel allocation.
• Support and cultivate a high-performing team culture with systems for learning, recognition, and continuous improvement.

What do we need from you?

Basic Qualifications

• 12+ years of experience in business and product operations, business strategy, and program management in a SaaS environment.
• 6+ years of people management experience, leading cross-functional and multi-disciplinary product operations teams.
• Proven expertise in software development methodologies such as Agile and Scrum, and in product lifecycle management.
• Strong communication and leadership skills with a demonstrated ability to align cross-functional executives and teams.

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 our Top Performer 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

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 People@calendly.com . Calendly is registered as an employer in many, but not all, states. If you are located in Alabama, 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.