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Outwitly Inc. seeks a detail-oriented, multitasking, and ambitious Executive Assistant Office Manager. This position will support the CEO and upper management in administrative functions. You will be the backbone of support so that management has what they need to seamlessly serve our clients and team’s needs.

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 several administrative tasks and are excited to help us continue that upward momentum.

While Outwitly is a fully remote company and all our employees work from home, we hope to find a candidate located in Winnipeg with access to a personal vehicle to work in person with the CEO occasionally. Note: We are still open to applications from candidates located elsewhere in Canada and would work 100% remotely – but some preference may be given to local Winnipeg candidates. 

Candidates must be able to work and attend meetings during regular business hours, M-F. 



  • Monitor, track and organize the 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, and booking flights and accommodations.
  • Conduct research and gather information as needed.
  • Managing and maintaining files in Google Drive.
  • Support ongoing improvements to business processes and SOPs (Standard Operating Procedures).
  • Creating and maintaining various office policies. Evaluate and implement new policies and procedures when needed. 
  • Provide support when required during hiring processes. 
  • 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.
  • Organizing, sorting and filing of receipts.
  • Available to be onsite occasionally for meetings, assisting with office work and running errands (if located in Winnipeg).
  • Perform administrative tasks as needed, including personal support – responsibilities will vary.



  • 3+ years experience in an executive assistant/office management role.
  • Post-secondary education in business administration.
  • Self-starter.
  • Excellent time management skills and ability to multitask and prioritize work.
  • Attention to detail and highly organized.
  • Good practical experience with online calendars and scheduling, particularly Google Calendar.
  • Proficient in Google Suite, Slack, Zoom, and Microsoft Suite.
  • Knowledge of Airtable would be an asset.
  • Flexibility to work additional hours when needed.
  • Since we are a remote team, it’s important that you’re well-organized and can manage your schedule.



  • Someone who loves systems, processes and organization.
  • A proactive thinker who can anticipate management needs.
  • Organized – excellent at time and project management, has clear systems and composure to handle multiple tasks simultaneously and ensures everything gets done promptly.
  • Can communicate with friendly professionalism.
  • Team player – proactively seeks opportunities to help others; will go above and beyond to complete the job.
  • 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 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) that 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 a new desk or chair, a carpet, or to cover your internet bill).
  • Company Benefits – After three months of employment, you can access 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 your resume and cover letter to or via Indeed with the subject line: Executive Assistant/Office Manager. 

Applications will be reviewed on a rolling basis. With the intention to fill the role by October 15, 2023

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