You enjoy setting the bar high and clearing it. Your ability to plan, prioritize, and execute projects/initiatives is matched only by your exceptional interpersonal skills and ability to drive collaboration in teams. You have a reputation as someone who never drops the ball. You have a keen eye for detail and efficiency and seek others who do as well.

The Chief of Staff is a catalyst that will help execute on behalf of the founders of the company, be a trusted advisor, and support their needs on critical tasks that require attention to detail, precise execution, and timely outcomes. This is an opportunity for a self-starter and visionary to work alongside the founders putting together the systems, processes and people to drive the business objectives forward, potentially translating to a senior operational leadership position.

And us? We are well funded and growing exponentially. Last year, our revenue grew faster than Uber when they were our size. We are building the world's most advanced tools for retail and e-commerce. Our customers include Fortune 500 companies such as Home Depot, local retailers such as Alexanian's, and leading brands such as Crate&Barrel. We are looking for obsessive and collaborative challenge-seekers to amplify our momentum and help us create an iconic Canadian tech company.

What You’ll Do

  • Report jointly to the CEO and Growth Officer
  • Work with the senior management team to prioritize projects, business strategies, and growth opportunities by setting explicit quarterly and annual goals
  • Institute operational and financial metrics based management of projects and groups in accordance with core strategies (and help build a culture of accountability by driving teams to meet those metrics and timelines)
  • Be the organization’s source of truth on the status of all projects and initiatives
  • Plan all aspects of monthly senior management meetings and company-wide town halls
  • Provide recommendations on operating and project-related improvements across the organization that will enhance coordination, communication, and efficiency
  • Promote the company’s core strategic plans, goals, and objectives while actively seeking out and removing any silos or bottlenecks hindering teams/workstreams
  • Advise on internal and external communications


  • A demonstrated ability to execute in a fast paced environment for multiple years (potentially at multiple organizations)
  • A high level of comfort with continuous change and improvement
  • A proven ability to exercise business judgement based on previous experience
  • A high degree of empathy and organizational EQ (promoting collaboration)
  • Proven ability to provide guidance, mentorship and support to ensure things get done
  • Exceptional problem solving skills and organizational skills with high attention to detail
  • Exceptional communication and time management skills
  • Be able to push back & ask difficult questions
  • High degree of discretion due to dealing with sensitive or confidential information

About our culture

  • We work in tight-knit teams to maximize speed and cultivate an ownership mentality.
  • We cherish curiosity and an obsession for details because we know these details are invaluable over the long run.
  • We promote an environment where ideas are challenged. The best ideas win!
  • We're hyperfocused on our achievements and our ability to execute on our promises. We act with urgency.
  • It's not always about us. We give back to our community to ensure it can grow.
  • We love to compete and have fun. Our game nights are legendary.

About our products

Our technology lets you see products in your own room before you buy. Imagine you want to redesign your home and have been searching for new tiles for your kitchen, or a new rug for your living room. You definitely want to make sure it will look good in your space. We enable that through cutting-edge computer vision technology, presented in an extraordinarily simple and accessible way. Try our rug demo now! Simply upload a picture of your room using your mobile phone, and slide the rug under your coffee table:

About our results

Our customers see a 5x increase in e-commerce conversion rates and a dramatic decrease in the time it takes for their customers to make a purchase decision. We are also reducing the world’s carbon footprint by eliminating trips to the store and avoiding product returns, while also saving marriages -- now you can be sure you’re buying the right product for your home.

About our office and remote work

We are located in downtown Toronto with nearby access to both of the main subway lines. Currently, we are all working from home; we encourage our teams to work from wherever they are most productive, and many of us will continue to work from home in the future, either full-time or partially. While we're all working remotely, we’ve come up with a few ways to keep everyone on the same page, including a quick company-wide check-in every Monday, remote coffee breaks on Fridays, and ad hoc topical sharing sessions. Another big upside is you get to be around your pets and plants (if you have them).

About our hiring process

Now: You upload your resume and complete a brief questionnaire.
Week 1: We arrange a video call with you to assess your abilities.
Week 1 or 2: You attend the first video interview.
Week 2 or 3: You attend the second video interview soon after.
Week 2 or 3: You receive an offer.

Take the Leap. Apply now.

Our demo, in case you missed it: