Sr. Director, Engineering

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
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.

A day in the life of a Sr. Director of Engineering at Calendly

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

What do we need from you?

• 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

Tier 1 Salary Hiring Range

$328,320—$426,816 USD

Tier 2 Salary Hiring Range

$300,960—$391,248 USD

Tier 3 Salary Hiring Range

$273,600—$355,680 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 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…