Senior Director, Software Engineering

Calendly; San Francisco (CA); On-site; USD 273,600 - 426,816; Full time

Benefits offered by this job

Top Performer Bonus

Equity awards

Competitive benefits

Job summary

Calendly is looking for a Sr. Director of Engineering to lead its engineering division in San Francisco. The role involves defining the vision and strategy for core products, mentoring engineering teams, and driving technological innovation. Ideal candidates should have over 15 years of software engineering experience and proven leadership in AI-driven environments. Competitive salary ranges from $273,600 to $426,816, and includes additional performance bonuses and equity options.

Qualifications

• 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.
• Comfortable driving adoption of modern engineering methodologies.

Responsibilities

• Define and execute the vision and strategy for product areas.
• Support and mentor a team of managers and engineers.
• Drive adoption of new technologies and methodologies.

Skills

Software engineering experience

Leadership experience

Building AI-First organizations

High-performance engineering teams

Distributed back-end systems

Modern engineering methodologies

Cloud platforms knowledge

Strong communication

Problem-solving skills

Passion for quality products

Tools

GCP

Job description

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 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? 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.

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 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 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 (Calendly does not engage in immigration sponsorship at this time)

Salaries

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 skill 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.

Geographic Pay Areas

• 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

Accommodation and Eligibility Information

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.

In order to provide a great interview experience, we record and transcribe interviews using Calendly Notetaker. If you prefer not to be recorded, please inform the host at the start of the meeting.

EEO Statement

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 not be used in the hiring decision.