Creative Director

San Francisco, California

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About Sentry

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster, so we can get back to enjoying technology.

With more than $217 million in funding and 85,000 organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

About the role

Sentry is a company with a healthy appreciation for design, art, and whimsical mischief. The Sentry Creative team strives to perfect the visual equivalent of puns. Our team reports to Design (so the creative people are managed by other creative people) and handles art, design, and copywriting for all mediums that are not product design (those folks are our other peers within the Design team).

We're looking for a Creative Director to lead our small, scrappy, and salty Creative team. We've got a great brand in place and are looking for someone that can advocate for the team at the leadership level, ensure the team has a creative environment to thrive in, and help guide the team as they develop their ideas.

In this role you will

  • Manage and lead a team of 10 people that grows slowly and intentionally, and covers the areas of illustration, copywriting, video, animation, web and print design, and swag production
  • Represent and preserve the rules and standards of the Sentry brand. And make sure we keep using Oxford commas
  • Work closely with Marketing and other creative partners during all points of the project cycle
  • Mentor and guide a diverse set of creatives, ensuring their personal and professional growth
  • Be the person ultimately responsible for the quality and success of the team and their work

You'll love this job if you

  • Think of yourself as a lead-from-behind sort of director — finding validation in your team’s success
  • Are an empathetic manager that understands the specific nuances of managing creative people
  • Optimize around your team’s ideas and abilities
  • Feel familiar and comfortable in the developer tools space. Our brand is dumb jokes about code being bad
  • Are a good balance of right and left brain, able to get weird with ideas, but hone them into deliverables that make sense
  • Have a multi-disciplinary background and skillset
  • Are wary of marketing cliches, uninspiring copywriting, and questionable social media choices

You will work on the team that has:


  • 8+ years experience as a Creative Director, Head of Design, or similar creative leadership role. This shouldn’t be your first rodeo
  • A strong background in art direction. You’ve produced and directed illustrative work that moves us
  • A portfolio that clearly communicates your role in the work
  • Experience in developer tools, code, or tech oriented companies
  • Strong writing and communication skills

The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $160,000 to $270,000. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans/programs.


Equal Opportunity at Sentry

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.

If you need assistance or an accommodation due to a disability, you may contact us at

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