Remote Executive Assistant / Software-Savvy Generalist

Full-Time | Remote | Work Directly With the Founder

I manage a portfolio of companies and investments across multiple industries, and I’m looking for a smart, highly capable, and tech-oriented Executive Assistant to help me stay organized, move faster, and operate at a high level.

This is not a traditional assistant role. I'm looking for someone who can act as my right hand — comfortable managing operations behind the scenes, running my inbox and calendar, coordinating with team members, and continually optimizing how I work across multiple businesses.

If you have a passion for software, systems, or design — even better. This role is ideal for someone with a blend of executive support skills, tech fluency, and sharp organizational instincts.

I encourage you to apply even if you don’t have every skill listed — what matters most is that you’re a fast learner who can keep up and grow with me.

Bonus Skills (Not Required, But Highly Valued)

If you’ve worked with any of the following, please mention it:

• Spreadsheets: Google Sheets, Excel (formulas, dashboards, reporting)

• Design tools: Canva, Revit, Blender, Figma

• Project/Construction tools: Primavera Cloud, permit tracking, scheduling software, Trello, Asana, Monday.com

• Coding: HTML, CSS, JavaScript, React, Python

• Marketing & Data: Google Ads, BI dashboards, CRM tools, data management

• No-code/automation: Notion, Airtable, Zapier

• AI Tools: ChatGPT, Claude, and others

What You’ll Do

• Manage and prioritize my inbox (drafting, responding, organizing)

• Own calendar management and cross-timezone scheduling

• Track deliverables and follow-ups across multiple businesses

• Handle task management and ensure effective delegation

• Summarize research, meetings, and business updates

• Create reports, slide decks, dashboards, simple no-code websites, and more

• Build or refine systems that improve workflows and visibility

• Coordinate with internal team members discreetly and efficiently

• Occasionally assist with personal admin, travel, or errands

You Are

• Hyper-organized, reliable, and resourceful

• A fast learner and clear communicator (especially in writing)

• Independent and proactive — you don’t wait to be told what to do

• Fluent in English (spoken and written)

• Comfortable with tech and eager to improve workflows

• Experienced working with founders, execs, or fast-moving teams

Logistics

• Remote – open to candidates worldwide (LATAM, Eastern Europe, SE Asia ideal)

• Full-time

• $1,000–$4,000/month depending on experience

• Flexible hours, with some overlap with EST preferred

• Long-term role with room to grow in scope and responsibility

Soft Skills

This role demands more than just execution — I’m looking for a partner who brings energy, intelligence, and collaboration into our work.

• Excellent English communication – able to explain complex ideas clearly in writing and speaking. Bonus if you speak multiple languages.

• Team player – collaborative, open-minded, and easy to work with.

• Proactive and innovative – takes initiative, solves problems creatively, and aims to deliver excellent work.

• Startup mindset – comfortable with shifting priorities, wearing many hats, and making fast decisions.

How to Apply

Please send the following to [email protected]:

• A short note introducing yourself and why this role excites you

• A link to your resume or LinkedIn

• Brief examples of past experience in a similar role

• (Optional but appreciated): A short video (max 2 minutes) introducing yourself

In addition, please answer the following four questions in your email or application:

1. If I gave you zero onboarding but full access, what’s the first thing you’d do in your first 24 hours?

2. What’s one weird or unique skill or obsession you have that you think would be useful in this role?

3. Write a short, professional reply to this message: “Hey, can you hop on a call today?” (You’re slammed and the request is vague.)

4. Send me a list of 3 tools or frameworks you'd use to manage my time, tasks, and communications. Briefly explain how you'd use them.

Salary and compensation

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.

Salary and compensation

Benefits

🌎 Distributed team

⏰ Async

🤓 Vision insurance

🦷 Dental insurance

🚑 Medical insurance

🏖 Paid time off

💰 401k matching

🏔 Company retreats

🏬 Coworking budget

🖥 Home office budget