DevOps Engineer

Remote, anywhere

Whimsical is the thinking and collaboration tool for distributed work. Our software helps thousands of customers—from individuals to Fortune 500—to work together more effectively.

Whimsical is expressive, fast, and delightful. We believe that software should spark joy, not dread.

We’re now looking for a DevOps Engineer to help move that vision forward!

We understand that DevOps is a broad and sometimes loaded term, and while in the future we would love for this role to go in the direction of holistic DevOps, the immediate needs for this role would be:

  • Cloud Infrastructure engineering
  • Developer Productivity engineering

Day-to-day work

At Whimsical you can expect your day-to-day to include:

  • Managing infrastructure: One of your primary tasks would be to manage Whimsical cloud infrastructure to ensure continued smooth sailing, up-to date cloud practices and continued compliance with the standards we abide by.
  • Improving developer productivity: Second main task would be to work with other developers to figure out how to help them maintain velocity of delivery. This includes everything from daily task automation, working on deployment system, improving our CI/CD setup, etc.
  • Support the team: Review pull requests, refactor code, help with both technical and non-technical issues and in general help each of us end the day better than when we woke up.
  • Taking on-call duties in your time zone: We try to take advantage of the fact that we're a small, geographically distributed team by delegating the first-responder duties to the people who are awake at that particular moment.

Our back-end stack is Clojure, Postgres, Redis, ECS, and is AWS based.

Our front-end stack is Cljs, Reframe, Reagent, among others.

Our Infra stack is Terraform, AWS, RDS, Container based deployment on ECS, GitOps for deployments, and Datadog for monitoring.

Indicators that this could be a good role for you
  • You feel that our philosophy resonates with you and you can see it guiding your decisions while at Whimsical.
  • You feel strongly about helping others be as productive as they can, and gain satisfaction from optimising their development experience.
  • You have 5+ years of software development and/or cloud systems administration experience (Bonus: experience working on internal developer tooling/experience)
  • You have experience working with JVM based services in production environments (Bonus: experience with Clojure specifically)
  • You have experience building and maintaining complex systems.
  • You have strong previous experience running systems in the cloud (Bonus: specific experience with AWS and GCP)
  • You have previous experience with running production workloads in containers (Bonus: specific experience with AWS ECS)
  • You have experience in measuring, analyzing, and fixing performance problems in a distributed systems.
  • You're able to work autonomously and stay self-motivated. (Bonus: previous experience working on remote team).
  • You are fluent in English.


  • Due to legal and compliance reasons we’re looking for someone in either
  • 🇺🇸🇨🇦North America
  • 🇪🇺European Union
  • 🇬🇧United Kingdom
  • A resume or manually entered experience (you can choose your preference).
  • Thoughtful, thorough responses to all the application questions.


  • 100% Remote: We’re spread from California to Latvia and we’ve got you covered if you prefer to work from a coworking space
  • Salary: Annual salary starting at $147,000 up to $184,000 (depending on experience)
  • Equity: starting at 0.12% (depending on experience)
  • Vacation: 6 weeks of paid time off each year
  • Parental Leave: 4 months paid by company
  • Equipment: We provide all the tech you need to work successfully
  • Summits: We try to bring everyone together at least twice a year
  • Pension*: 401k with 6% company matching
  • Health Insurance*: Paid by company for you and dependents

* Availability may depend on your location and our current administrative capabilities there.

How we work

We use an adapted version of Basecamp's Shape Up approach, which for us means:

  • We work in cycles of 5 weeks of focused work and 1 week of cool down.
  • Each 5 week work cycle sees one or more "bets" shipped, each having very specific and well defined requirements.
  • During cool down, each of us choose what we want to work on, be it bugs, minor features, tech debt, exploring new concepts, and more.
  • Each of us can create an "idea pitch" for an upcoming cycle, and move our ideas along.

As a DevOps Engineer at Whimsical, you'll be mainly focusing on our cloud infrastructure and helping developers be more productive, whether it be by working on automation, scripts, CI/CD setup or other aspects of productivity. And being a small company means that sometimes contributing to other areas of the product, including Back-end or Front-end shouldn't be a deal-breaker to you.

In addition to Shape Up, we also occasionally roll up our sleeves and do customer support to better understand our users and their needs, regardless of our role within the company.

Our primary mode of operation is asynchronous. We use real-time communication with great care, and only where it makes sense. We use Whimsical, email, Slack, and Zoom for our day-to-day communication.

But we also believe in spending quality time together, which is why we try to bring everyone from around the world together at least twice a year for what we call "Whimsical Summits". At Summits we focus on getting to know each other better and building bonds that help us communicate better when we're apart. The ongoing global pandemic has prevented us from doing this for the last couple of months, but we hope to go back to this mode of operation as soon as possible.

About Whimsical

Whimsical was founded in 2017 by Kaspars Dancis and Steve Schoeffel to help people think and collaborate in the digital-first work environment.

Whimsical's product is expressive, fast, and delightful. We believe that software should spark joy, not dread.

We are a remote-first company and big proponents of remote work because it democratizes the opportunities for people everywhere.

Our operating philosophy is based on set of core principles, such as:

  • Sustainability: We don't believe in growth at all costs. Growth is a fundamental part of a healthy existence but we want it to be in balance with sustainability and bounded by ethical behaviour. We strive to work calm, 40-hour work weeks. Whimsical is also committed to doing our part towards sustainable future for the planet.
  • Craftsmanship: We care deeply about our work. We are specialists, eager learners, and persistent in our pursuit of quality work. We're patient and committed because building great things takes time.
  • Long-term focus: We're building Whimsical for the long-haul, not a quick exit. We avoid shortcuts and consider every key decision from a 10+ year perspective.
  • Partnership Mindset: We’ve built the company around the idea that everybody who joins us should feel like they are partners in the business. Time is precious and we want Whimsical to be the place where people invest their time rather than sell it. Our equity offers are 100% transparent and above market average. We also pay everyone at the same level the same salary, no matter where they live.


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