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 an experienced Senior Engineering Manager to help move that vision forward!

As the Senior Engineering Manager, you will be managing a group of 6-8 engineers. You will ensure that they collaborate effectively, that the group has the right skills and capabilities, and that everyone in the group is excited to contribute.

You will also partner with Tech Leads of our product teams. While you will be responsible for the people on the team, the Tech Lead will be responsible for the technical direction and delivery of the team.

Day-to-day work

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

  • Ensure that your team has the right people to deliver on its objectives. You will do so through hiring, training, and performance management.
  • Coach the members of your team to support them and to help them grow professionally.
  • Work with your teammates to ensure that they get to work on challenging problems, are excited to contribute, and are recognized for their contributions.
  • Build trust-based relationships with the members of your teams through 1:1s to facilitate effective feedback and flow of information.
  • Lead different rituals and facilitate conversations to ensure that your teams collaborate effectively.

Indicators that this could be a good role for you:

  • You’ve successfully managed teams of Engineers in the past (minimum of 3 years experience).
  • You have considerable previous experience as a Software Engineer.
  • You feel that our philosophy resonates with you and you can see it guiding your decisions while at Whimsical.
  • You are able to communicate in English clearly both verbally and in writing.
  • You are able to attract other great people to work with.
  • You can motivate and inspire.
  • You have courage and the ability to have difficult conversations candidly and empathetically.
  • You can manage your own time and prioritize your work.
  • You always looking to refine your methods by collaborating with your manager and peers.


  • We’re looking for someone to guide teams from (Eastern and Central Time Zones)
    • 🇺🇸 US (Eastern and Central Time Zone)
    • 🇨🇦 Canada (Eastern and Central Time Zone)
  • A resume
  • Thoughtful, thorough responses to all the application questions.


  • 100% Remote: We currently have teammates in New Zealand, North America, Europe, and we’ve got you covered if you prefer to work from a coworking space
  • Salary: Annual salary at $184,631
  • Equity: ~0.3%
  • Vacation: 6 weeks of paid time off each year
  • Parental Leave: 4 months paid by the company
  • Equipment: We provide Apple hardware and all the other 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 the company for you and your 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.
  • We work in product teams, where each team owns the features and execution of certain product areas.
  • Each team owns creating “idea pitches” for upcoming cycles, and moving their product ideas along.
  • Each 5 week work cycle sees one or more “bets” shipped for each team, each having very specific and well-defined requirements.
  • During cool down, each of us chooses what we want to work on, be it bugs, minor features, tech debt, exploring new concepts, and more.

As the Senior Engineering Manager at Whimsical, you’ll be contributing by ensuring the well-being of the Engineering team and making sure that any blockers are removed efficiently and problems are being solved. And being a small company means that on rare occasions you may have to roll up your sleeves and help with some code.

In addition to Shape Up, we also occasionally pitch in 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.

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.

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 behavior. 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.