Sr. Director, Engineering
Quick Summary
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.
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.
On a typical day, you will be working on:
- Defining and executing the vision and strategy for a key product area aligning with the Calendly’s goals and priorities
- Supporting and mentoring a team of managers and engineers, providing technical guidance and coaching on their career development
- Driving innovation and adoption of new technologies and methodologies that enhance Calendly’s services
- Ensuring the quality, performance, security, and scalability of a product line of business following best practices and standards
- Collaborating with other engineering teams, product managers, and stakeholders to understand the business requirements and deliver solutions that meet or exceed expectations
- Driving innovation and adoption of new technologies and methodologies that core capabilities and user experience
- 15+ years of software engineering experience, with at least 10+ years in a leadership role
- Experience helping to build and scale an AI-first engineering organization, including integrating AI/ML capabilities into core services, developer workflows, and product strategy
- Experience leading high-performance engineering teams
- Experience building highly-available distributed back-end systems
- Comfortable working as a change-agent, and drive adoption of modern engineering methodologies
- Knowledge of cloud platforms, such as GCP and their services and tools
- Experience operating in both high-growth startup technology companies and larger, more established organizations, with the ability to adapt leadership style and processes to each
- Strong communication, collaboration, and problem-solving skills
- Passion for delivering high-quality products and services that delight customers
- Ability to iterate and ship fast
- The ability to work in our San Francisco office 2 days per week
- Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time
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
This role may require occasional travel for company events, team collaboration, or offsites.
Location & Eligibility
Listing Details
- Posted
- May 1, 2026
- First seen
- May 1, 2026
- Last seen
- May 5, 2026
Posting Health
- Days active
- 3
- Repost count
- 0
- Trust Level
- 79%
- Scored at
- May 5, 2026
Signal breakdown

Calendly is your scheduling automation platform for eliminating the back-and-forth emails to find the perfect time — and so much more.
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