This job is perfect for:
- Someone with ~2-4 years of related job experience looking to build their skills OR
- Someone burned out by internal grind culture at a full-time role who wants more flexibility and a relaxed environment OR
- Someone who’s been out of the workforce for awhile but is ready to reinvigorate their career by watching YouTube tutorials, networking, and learning new skills
Our full-time team consists of our Founder/CEO and our Head of Operations. You’ll work extremely closely with both of us every day, as well as our various clients and Squad members. Collaboration and support is integral to the way we want to run our business.
Your role
As this role is new, the exact job description may change as we evolve. Below are some examples of the work we need support with, but we’re open to hearing about other valuable skills you bring to the table that will enable our growth.
The broad categories:
- Administrative stuff
- Managing the Squad Support inbox and responding to inquiries or escalating to the team.
- Supporting our internal Notion organization and eventually taking the lead on regular improvements, in conjunction with our Head of Operations.
- Sending SOWs and contracts via eSignature.
- Client-facing work
- Light client deliverables like organizing and managing their Google Drives and Notion pages.
- Creating client project proposals and managing their project set-ups. This means adding in client-ready copy to sell our services and adding in preliminary pricing.
- Ideating thought leadership content for our LinkedIn strategy, spearheading our company presence online.
- Updating our website, developing case studies, creating sales one-pagers: showing off the incredible work our Squad is capable of.
- Squad member support
- Leading our external Squad communications, being the point person for our network of freelancers.
- Reviewing submissions and helping to determine which applicants we need to work with, and who may not be a fit.
- Supporting Squad members with creating their bios in Notion (writing biographies, uploading photos and making sure they look great, light layout work, etc.).
- Answering basic Squad member emails about rates, timelines, invoicing processes, etc.
- Ensuring a consistent and awesome onboarding experience for our Squad members, eventually expanding to onboarding new clients.
General skills you’ll have:
- Highly organized and able to delegate both up and down.
- A self-starter who enjoys working both independently and collaborating with others.
- Able to multi-task while prioritizing what’s important, what’s urgent, and what’s neither.
- A positive attitude. We all make mistakes; as we tell our kids—apologize, make it better, and move on.
- Enjoys operating with a bit of ambiguity, knowing you have the ability to make an impact and personally shape how we operate.
✨ Bonus: You’re a budding graphic designer, content creator, web developer, etc. We’ll support your efforts and help you further your skills while creating awesome client work.
What you'll have going for you:
- An understanding that the Freelance Squad is a team of people with little kids, important pets, and great books to read. We all work different hours and there are no expectations that anyone needs to match someone else's time: you work when, where, and how it's best for you, as long as the work gets done.
- You love the Google Suite, totally dig Notion, and are a quick learner at other marketing tools (Asana, Figma, etc.).
- You're okay with operating with some unknowns, understanding that we’re a small business learning as we grow. You’re excited about the potential to help us shapre the future and love thinking about ways for us to improve.
- A fun energy that helps bring people up (but hey, everyone is entitled to off-days).
Things that are good to know
- This isn't a politics-free role: shit's too important for that. We believe in fighting climate catastrophe, reproductive rights, criminal justice reform, better education, and that Donald Trump and Doug Ford are poison.
- We're learning. This is a ferocious business run by two moms with three kids between them, two of them neurodivergent. We value our clients and our Squad members, but also our sanity. We know there are always improvements we can be making—we value you sharing what those are, and we do hope to get to them someday soon.
- You don't need set qualifications for this job. We know women, non-binary individuals, and minorities are consistently underrepresented, and don't deserve to be. Apply anyway if you know you would destroy this role.
- This is a client-facing and Squad member-facing role. It’s important that you feel excited about that and confident talking with new people.
Our interview process
1️⃣ Complete our intake form
We’ll review all applications by November 28, 2025
2️⃣ Film a short get-to-know-you video
We’ll contact Round 1 individuals to film a short Loom video for us. No pressure: this is just our way of getting to know you more without asking you to commit to a full interview. More info included if you’re selected.
3️⃣ Chat with us
You’ll meet on a call with our CEO and/or Head of Operations. We’ll ask questions, you’ll ask questions, we’ll get to know each other and the role.
4️⃣ Short exercise
Don’t worry—nothing super intense. This could be creating a short page in Notion, writing a cold email to a potential new client—we’ll let you know, but we don’t anticipate this taking more than 1 hour of your time. We expect ~5 candidates to reach this stage as we want to be conscious of your valuable time.
5️⃣ Try a paid contract
We’ll start with a short trial of 4 weeks (paid) to make sure it’s a good fit for all of us, as well as adjusting the job description if needed so that we utilize your talents the best way we can. We expect 1 candidate to reach this stage.
6️⃣ Join the team
If everything goes to plan, we’ll extend a full offer to you to join our team. Exciting!
Details + compensation
- Estimated time: 40 hours/week
- Rate range: $45,000 - $65,000 based on experience and fit
- 3 weeks of paid vacation (plus office closures for a week during winter holidays)
- Flexible work hours
- Company laptop (including partial compensation for your cell phone plan)
- Entirely remote (our two FT team members both work in Toronto and meet up ~4 times a year, but this isn’t a requirement)
At our current scale, please note we do not currently offer benefits, parental leave top-up, or other really awesome and important benefits (though we’d love to get there some day!)