Senior Director, Software 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 a core Calendly product area that directly impacts user engagement and growth. In this role, you will lead a group of engineers that deliver customer-facing capabilities that power key user workflows and experiences

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 drive alignment and execution across cross-functional product teams

A day in the life of a Senior Director, 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 customer-facing products and user experiences.
• Delivering a high-quality, dependable product experience that meets customer expectations and scales with business growth
• Collaborating with other engineering teams, product managers, and stakeholders to understand the business requirements and deliver solutions that meet or exceed expectations
• Driving continuous improvement in how teams build and ship customer-facing features

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 acting as a change-agent, driving adoption of modern engineering methodologies
• Experience leveraging modern cloud technologies to deliver scalable customer-facing pr