Whimsical is an end-to-end SaaS platform for shaping ideas. Our software enables thousands of customers—from individuals to Fortune 500 companies—to think and collaborate in the new era of distributed work.

We’re now looking for a Head of Product Design to take part in our efforts to build tools that make online work better.

About the role

Whimsical is a product-led company that truly values design and craftsmanship. We strive to build world-class software that is fast, elegant, and insanely polished. Whimsical is extremely visual and our product vision is expansive. This means that design will always play a central role in everything we do. In short, this is an incredible place to be a designer.

We currently have 3 full-time product designers who are all very experienced and talented. Our co-founder, Steve Schoeffel, is also a designer. We are looking for a design leader who will help us scale design at Whimsical through leading and growing our current design team. We expect this role to include some hands-on product design work initially but transition more to full-time management and leadership as the team grows.

Our process is loosely based on Shape Up. We write a lot, comment, iterate and play (using Whimsical of course ;)) with our pitches. We work in a dual-track process where you as our Head of Product Design will help our teams shape and discover future products. Our product teams are cross-functional teams inspired by Marty Cagan’s two books Inspired and Empowered.

You will be reporting to our VP Product Niklas Stephenson.

Your responsibilities include:

  • Coach and lead our fantastic team of Product Designers.
  • Ensure that your team has the right people to deliver on its objectives. You will do so through hiring, coaching, and performance management.
  • Grow a culture of cross-team collaboration and open honest feedback.
  • Work closely with our co-founder Steve Schoeffel on leading design across Whimsical.
  • Drive, challenge, and develop our discovery process in partnership with the rest of the product and engineering leadership.
  • 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.

Your first quarter at Whimsical

At the end of your first quarter at Whimsical you will:

  • Feel at home, know the awesome people here and how we work
  • Get to know our design and product process and start to impact it
  • Have a good connection with our current product designers and do weekly 1:1s with them
  • Started to do cross-team design critique
  • Collaborated on pitches and research for upcoming product features


  • You’ve successfully managed teams of product designers in the past.
  • You have considerable previous experience as a Product Designer.
  • 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 our design team from either
    • 🇺🇸🇨🇦North America
    • 🇪🇺European Union
    • 🇬🇧United Kingdom


- 100% Remote: We’re spread from New Zealand to Latvia and we’ve got you covered if you prefer to work from a coworking space.

- Salary: Annual salary starting at $230,789

- Equity: starting at 0.5%

– Vacation: 6 weeks of paid time off each year

– Parental Leave: 8 weeks 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 when possible

 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.

You can read more about how we think about compensation on our blog.

About Whimsical

Whimsical was founded in 2017 by Kaspars Dancis and Steve Schoeffel to help teams be more effective in the distributed and fully digital 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 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.