People Operations Specialist

  • Freelance
  • Anywhere


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

About The Role

As the People Operations Specialist you will oversee and manage all day-to-day operations of the employee lifecycle at Whimsical. We are looking for an experienced and organized professional to join our Operations team.

Whimsical is a distributed company of ∼40 employees across North America, Europe and New Zealand. You will work closely with the department managers, as well as with external legal counsel and accounting teams.

Your responsibilities include:

  • Lead recruiting efforts including job postings, sourcing, candidate vetting, and offer management
  • Assist department managers with employee onboarding, offboarding, as well as scaling and increasing headcount
  • Plan, coordinate and implement processes, policies, and surveys to support the organization’s people compliance and strategy needs
  • Execute on standard administrative tasks, including drafting and maintaining benefits and policies
  • Help with planning and organizing company events both online and offline
  • Work with our existing tool stack (e.g. Rippling, Deel) and introduce new tools and processes

Your first quarter at Whimsical

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

  • Feel at home, get to know the awesome people here and learn how we work
  • Understand Whimsical employment setup in the US, Denmark, Latvia and other countries with remote employees
  • Understand employee lifecycle at Whimsical, help with employee onboarding
  • Collaborate with the Operations team on process improvements and organizing first team events

Indicators that this could be a good role for you
  • You have proven track record of working in HR administration, people operations, or similar roles at a high-growth startup
  • You have understanding of tax, legal, and localized benefits, and experience with employment in the United States in particular
  • You have exceptional admin skills and attention to detail
  • You have bias for action and ability to follow through swiftly
  • You are able to communicate in English clearly both verbally and in writing
  • You can manage your own time and prioritize your work
  • You are comfortable to work independently and collaborate with others
  • You feel that our philosophy resonates with you
  • You are based in:
    • 🇺🇸🇨🇦North America (East Coast)
    • 🇪🇺European Union
    • 🇬🇧United Kingdom

What We Offer
  • 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 $118,164
  • Vacation: 6 weeks of paid time off each year
  • Parental Leave: 4 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
  • 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.

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.

To apply, please visit the following URL:→