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Outwitly Inc is seeking a detail oriented, multi-tasking, ambitious Executive Assistant Bookkeeper. This position will support the CEO and upper management in clerical and accounting functions. You will be the backbone of support so that management has what they need to seamlessly serve the needs of our clients and team. 

We are a boutique consulting firm specializing in UX and service design. Our team is small and tight knit, but growing fast! We are looking for someone to help us manage a number of administrative tasks and are excited to help us continue that upward momentum.

Outwitly is 100% remote. We are looking for candidates to work remotely within Winnipeg, Manitoba. Candidates must be able to work and attend meetings during regular business hours M-F. 


  • Monitor, track and organize CEO’s email/inbox and calendar 
  • Takes notes during meetings, documenting action items and following up until items are complete.
  • Assist in organizing special events; booking flights and accommodations 
  • Conduct research and gather information as needed 
  • Organizing files in the Google Drive 
  • Support ongoing improvements to business processes and SOPs (Standard Operating Procedures) 
  • Assist in updating the contractor database on an ongoing basis. 
  • Proof-read and add polish to documents as required
  • Be able to assist in data entry work for accounts payable and receivable; ensuring invoicing and billing is received promptly and accurately. 
  • Organizing, sorting and filing of receipts 
  • Available to be onsite occasionally for meetings, assisting with office work and running errands.
  • Perform various administrative tasks as needed, including some personal support – responsibilities will vary 


  • 3+ years experience in an executive assistant/bookkeeping role 
  • Post-secondary education in business administration 
  • Attention to detail and highly organized
  • Good practical experience with online calendars and scheduling٫ particularly Google Calendar
  • Solid understanding of bookkeeping principles
  • Proficient in Google Suite, Slack, Zoom, Microsoft Suite, and QuickBooks
  • Knowledge of Airtable would be an asset
  • Flexibility to work additional hours when needed. 
  • Access to a reliable vehicle 
  • Since we are a remote team, it’s important that you’re well organized and can manage your own schedule.


  • Someone who loves systems, processes and organization 
  • A proactive thinker who can anticipate managements needs
  • Organized – excellent at time and project management, has clear systems and composure to deal with multiple tasks at once and ensures everything gets done in a timely manner
  • Can communicate with friendly professionalism 
  • Team player – proactively seeks opportunities to help others; will go above and beyond in order to get the job done
  • Well-developed written and verbal communication skills in English are a must have.
  • Trustworthy – as you are privy to confidential information
  • Self-Motivated – a “can-do” attitude who is excited to help grow Outwitly just as much as are!  



Outwitly Inc. is a UX & service design consultancy based in Ottawa and Winnipeg. We use design thinking and human-centered design and research to solve complex business problems, and we work closely with our clients to create end-to-end user and customer experiences that are delightful and consistent across all channels and touchpoints. 

Outwitly’s mission is to challenge the status quo and create innovative solutions to improve people’s lives. Our services include UX design, UX research, service design, staffing, and training. 



  • 100% Remote Work Environment – We offer a flexible work environment, if you need to take off for an appointment or get life stuff done, we won’t check up on you as long as you can get your work done and are available for meetings! Our employees are located across Canada too.
  • Disconnect From Work Policy – We firmly believe in work-life balance, Outwitly has a policy in place to remind everyone that they should check-out of work on evenings and weekends. 
  • Professional Development Funds – Learning is so important! Every employee has access to a yearly professional development budget (after three months of employment) they can use to attend webinars and conferences, or purchase online courses and books.
  • Remote Working Stipend – After three months of employment, you’ll have access to a yearly remote working budget to spend on anything that makes your work easier or more enjoyable (whether that’s a new desk or chair, a rug, carpet, or to cover your internet bill).
  • Company Benefits – After three months of employment you’ll have access to our company’s benefits program.
  • Wellness Spending Account – After three months of employment you’ll have access to a WSA to expense gym memberships, vet care bills, and trips to the spa!


Please submit resume and cover letter to by Feb 10th, with the subject line: Virtual Executive Assistant Bookkeeper 

Or apply through LinkedIn or Indeed.

Applications will be reviewed on a rolling basis. With the intention to fill the role by March 6, 2023

Please note that you must already be legally entitled to work in Canada.