An Important Note about Wayfair's In-Office Policy and Salary: 

Please note that this is a hybrid role based in Toronto, CAN, and will require you to work in the office on Tuesdays, Wednesdays, and Thursdays.

 

The salary range for this position is $151,411 - $169,169 CAD per year. The base salary offered may vary depending on location, job-related knowledge, skills, and experience. Restricted stock units will also be provided as part of the compensation package.

 

Who We Are

Wayfair is a dynamic, cutting-edge technology company operating in the ecommerce space. We’re committed to providing our customers with a best-in-class experience for all things home. We’re looking for an experienced Senior Endpoint Engineer for a growing, global End User Computing Engineering team. The team is responsible for corporate device management, including more than 20,000+ computers, virtual desktops and mobile devices.

This position includes ~10% travel to retail locations to partner with on-site staff, leadership, and operations teams.

What You’ll Do

• Develop and manage deployment strategies for POS devices and retail-specific endpoints, including software distribution, patching, and lifecycle management.
• Support and enhance the broader corporate endpoint environment, including Windows, Mac, ChromeOS, VDI, and mobile devices.
• Partner with Retail Operations, Store IT, and corporate teams to design and implement retail technology solutions that are reliable, secure, and scalable.
• Act as an escalation point for retail endpoint issues, while also supporting general endpoint escalations across the enterprise.
• Participate in store visits (~10% travel) to evaluate technology in the field, collaborate with retail staff, and identify opportunities for improvement.
• Analyze and resolve complex onboarding and deployment challenges for both retail and corporate use cases.
• Develop plans for 3rd party software management, update cadences, and testing frameworks across both retail and corporate environments.
• Proactively monitor, report on, and remediate systemic endpoint issues at scale, leveraging tools such as Intune, SCCM, Jamf, Google, or other endpoint/POS management systems.
• Document workflows, infrastructure, and support playbooks to ensure consistent retail IT practices across all locations.
  
  

We Are a Match Because You Have:

• 3-5+ years of experience managing large-scale endpoint environments (10,000+ devices) with exposure to both corporate and retail IT systems.
• Hands-on experience with point-of-sale (POS) platforms and supporting retail infrastructure.
• Strong background with enterprise endpoint management tools such as Microsoft Intune/SCCM, Google, or Jamf.
• Proven ability to balance general endpoint engineering responsibilities with specialized retail IT support.
• Excellent troubleshooting and problem-solving skills for both corporate and retail-specific issues.
• Familiarity with secure payment systems, store networking, and in-store endpoint reliability best practices.
• Strong automation skills with PowerShell, Python, or Shell scripting.
• Ability to communicate effectively with retail associates, IT staff, engineers, and executives, adapting style to the audience.
• Willingness to travel (~10%) to retail locations to partner with on-site staff and leadership.
• Strong organizational skills with the ability to juggle multiple initiatives in a dynamic, global business environment.

 

Why You'll Love Wayfair

• Time Off:
• Paid Holidays
• Paid Time Off (PTO)
• Paid Sick Days
• Health & Wellness:
• Health & Dental Benefits 
• Life Insurance
• Disability Protection (Short Term & Long Term Disability) 
• Global Wellbeing: Gym/Fitness discounts
• Mental Health Support (Global Mental Health, Global Wayhealthy Recordings)
• Caregiver Services
• Financial Growth & Security:
• RRSP (Registered Retirement Savings Plan)
• Tuition Reimbursement 
• Family Support:
• Parental Leave Top-Up Program
• Global Surrogacy & Adoption Policy
• Professional Development & Recognition:
• Rewards & Recognition 
• Global Employee Anniversary Awards 
• Paid Volunteer Work 
• Unique Perks:
• Employee Discount 
• Global Pod Outings
• Work/Life Balance:
• Emphasizing a supportive & flexible work environment that encourages a balance between personal and professional commitments

We are looking forward to your application!

About Wayfair Inc.

Wayfair is one of the world’s largest online destinations for the home. Whether you work in our global headquarters in Boston, or in our warehouses or offices throughout the world, we’re reinventing the way people shop for their homes. Through our commitment to industry-leading technology and creative problem-solving, we are confident that Wayfair will be home to the most rewarding work of your career. If you’re looking for rapid growth, constant learning, and dynamic challenges, then you’ll find that amazing career opportunities are knocking.

No matter who you are, Wayfair is a place you can call home. We’re a community of innovators, risk-takers, and trailblazers who celebrate our differences, and know that our unique perspectives make us stronger, smarter, and well-positioned for success. We value and rely on the collective voices of our employees, customers, community, and suppliers to help guide us as we build a better Wayfair – and world – for all. Every voice, every perspective matters. That’s why we’re proud to be an equal opportunity employer. We do not discriminate on the basis of race, color, ethnicity, ancestry, religion, sex, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, veteran status, genetic information, or any other legally protected characteristic.

Your personal data is processed in accordance with our Candidate Privacy Notice (https://www.wayfair.com/careers/privacy). If you have any questions or wish to exercise your rights under applicable privacy and data protection laws, please contact us at dataprotectionofficer@wayfair.com.