Full Time
$4/hour
40
Oct 16, 2026
Do you believe in work/life balance and managing yourself based on due dates, not timesheets?
Are you a positive person and always looking to create win-win opportunities?
Do you have fun in life, enjoy teaching and helping others around you?
If you are ok with keeping things the way it’s always been done and not challenging the norm, this role is NOT for you.
Still reading? Great, you will likely fit right in here.
Why Us?
UpSide Accounting exists to create wealth and freedom for creative professionals. When given the freedom to create they vastly improve their communities and make a larger impact on society as a whole. To do this we build creative accounting solutions utilising state-of-the-art tech and employ virtual accounting pros to leverage them. In fact, Intuit recognized us as the Canadian runner-up in the 2016 Firm of The Future contest. We’re a little different….we’re not for everyone. We are also a small but mighty team and you can make a large difference here.
As a Bookkeeper, you will be:
Manage weekly bookkeeping tasks, ensure a high level of accuracy and assist with creating and filling various accounting reports/remittances as needed
Identify opportunities to improve workflows and assist with implementation of new tech/tools to support the team
Collaborate with a small team of accounting pros in various roles, ensuring the quality of work is high and deadlines are met or exceeded.
Contributing to the overall strategy and growth of the firm. Documenting workflows, recording short video responses to common questions and identifying opportunities to better serve our clients are a few examples.
Grow with us and transition into other leadership roles as opportunities arise by building a career enhancement plan and attending semi-annual reviews to adjust
Our hiring process:
If this sounds like a match made in heaven for you then we would love to hear from you.
Requirements:
You have experience (or even certified) with QuickBooks Online, Hubdoc, Dext and other 3rd party apps
You are comfortable giving feedback/training to others
You are comfortable analyzing complex situations and providing your advice to decision-makers
You are always seeking a better way to do things and how technology can assist
You communicate very well (both written and verbal) and with respect
You like to-do lists, checkmarks, everything in its place and reconciled
You enjoy cool new gadgets and apps. You have run out of space on your smartphone and had to keep only your most-used apps.
You feel a sense of responsibility to see tasks through to completion.
You like taking charge of the tasks you are responsible for. Sometimes this means being resourceful with the data and tools available.
Your own computer/laptop to access the internet
You have a strong internet connection - at least 18MBPS upload and 4MBPS download speeds
A webcam and headphones that can be used during online meetings with the team
Assets:
Canadian experience at an accounting/bookkeeping firm working with dozens of clients
You are interested in Blockchain or even own cryptocurrencies
You have a creative side and like photography, writing, creating/editing videos or painting
How we define success for your role:
We are results-based, which means we care about:
A predetermined number of jobs closed each month
Percentage of work items completed before & on the due date
Percentage of overdue jobs at any given time
Number of continuing education credits earned
Number of continuing education credits your team has earned
Your team’s feedback on your communication and leadership
Your client’s feedback on your communication and leadership
NOT timesheets, number of hours or what times of the day you work
What is it like working at UpSide?
Growth - We are constantly looking to improve. By holding regular lunch & learns and attending webinars on various topics we stay informed in a fast-paced world.
Collaborative - We value everyone’s input because everyone is unique. We have an open and honest environment that is dependent on positivity.
Remote - We are not your traditional 3 piece suit, 9-5 kind of firm. We work from home on our own schedule as long as deadlines are met. With this level of autonomy, we are going to have to really trust you, so we have built a multi-step video interview process.