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.
Calendly is evolving into a multi-product platform that helps individuals and businesses orchestrate work more effectively. As a Design Director, you will co-lead a Product Group and the broader Design Team to play a pivotal role in shaping strategy, vision, and execution.
This is a leadership role accountable for both user outcomes and business outcomes within your Product Group. You will partner closely with the Director of Product and Director of Engineering to define direction, set ambitious goals, make user-focused decisions, design easy-to-use products that create value for customers, and ensure high-quality execution. You will also be a major contributor to the overall design organization, elevating design standards, fostering a healthy creative community, and growing and supporting a high-performing, impactful team.
This role requires strategic creativity, customer focus, collaborative leadership, operational rigor, and thoughtful people leadership.
A day in the life of a Design Director at Calendly
On a typical day, you will:
- Co-lead a Product Group in partnership with Product and Engineering Directors, defining and executing on vision, strategy, and roadmap, based on customer needs and insights.
- Own and deliver measurable user outcomes and business results for your product area.
- Set and drive a clear design vision that ensures cohesive, high-quality, end-to-end user experiences across the Product Group.
- Provide clear, actionable feedback and coaching to designers that improves usability, quality, and design decision-making.
- Ensure teams conduct meaningful research and use customer insights and data to inform product strategy and decisions, driving toward measurable outcomes.
- Co-lead the Design Team by hiring, coaching, and developing a diverse, high-performing group of designers, actively supporting career growth and engagement.
- Drive adoption and improvement of the design process and R&D operating model to increase quality, usability, cohesion, and customer impact.
- Use compelling design storytelling to influence stakeholders, align leaders, and advocate for customers at the team, product group, and company levels.
- 12+ years of experience designing and delivering high-quality design work and impactful product experiences, including meaningful time in leadership roles.
- 3+ years of people management and design leadership experience, including hiring, supporting, and growing empowered creative teams.
- Experience co-owning and scaling a product area with measurable customer and business impact alongside Product and Engineering partners.
- Proven ability to set product and user experience vision based on customer needs and translate strategy into execution.
- Strong executive communication skills and experience influencing senior stakeholders.
- Experience in product-led B2B or B2C environments; SaaS experience preferred.
- Experience working in complex systems and multi-product environments.
- Experience designing AI-driven product experiences and using AI effectively in the design process is a plus, but not required.
- 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
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.
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What We Do
At Calendly, we are excited about changing the way the world schedules. We are a profitable company, offering ample opportunities to accelerate your career. We’re obsessed with providing an elegant, delightful experience for our customers. This shapes how we develop, design, market and support. We work hard, move fast and pitch in across departments—and always make time to celebrate our accomplishments. Join a diverse workforce, leading the way in scheduling automation. Calendly, a powerful yet simple automated scheduling tool, takes the work out of connecting with others so you can accomplish more. Millions of users benefit from an enjoyable scheduling experience, more time to spend on top priorities and flexibility to accommodate individual users and large teams alike. Calendly works with Google, Office 365 and Outlook calendars and apps like Salesforce, Stripe, PayPal, Google Analytics, GoToMeeting and Zapier for a seamless user experience.
