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Senior IT Support Engineer


Location: Remote -

Job Type: Full time

Last updated

Be brave, not perfect.
- Reshma Saujani

Have you ever tried to hire a plumber? How about a house cleaner? If you have, chances are it took you way longer than it should. In the era of instant-everything, you shouldn’t have to waste an entire afternoon researching, calling and vetting local service professionals whenever you need one. The market for hiring them is huge — $1 trillion in the US alone — but the process is inefficient and largely offline.

Thumbtack is transforming this experience end-to-end, building a marketplace that matches millions of people with local pros for almost any project. In making these connections, not only do our customers get more done every day, our pros are able to grow their businesses and make a living doing what they’re great at.

These customers and pros come from all walks of life and every county in the country. We want our team to reflect that. If you come from an underrepresented background in tech, we strongly encourage you to apply. We challenge ourselves every day to make this a place where you can thrive just the way you are, so we can build a product that does the same for our customers and pros.

About the IT Team

Our mission statement is to empower Thumbtack to do. IT enables Thumbtack to get things done. We excitedly engage teams, delivering services & support that empower everyone to do the work they love, so our only limitations are our imaginations—not our technology.

About the Role

As a Senior IT Support Engineer, you will be our first IT hire in Toronto, Canada and we are excited to continue to grow our global support team. You will be a customer service and support evangelist, assisting our customers via in person walk-ups, support tickets, email and chat. You will work closely with our Help Desk staff to build and maintain IT documentation and tools, coordinate schedules, manage IT queues, handle escalations and drive IT initiatives. You love building relationships with customers, business partners and IT team members alike. You have a strong background in Mac, A/V and network troubleshooting. You must have excellent communications skills, a passion for technology and dedication to providing the best end user experience possible.


  • Troubleshoot and resolve advanced issues with hardware, software, applications & networking, provide timely resolution of problems, and act as escalation point for the team and customers
  • Own and drive IT projects and deliverables under the direction of IT leadership
  • Help lead and manage A/V events, systems and support
  • Handle system access and maintain user accounts, passwords, data integrity & security
  • Manage relationships with vendors and 3rd party providers and oversee inventory, purchasing, asset management and other key processes to support IT
  • Participate in interviewing, training and mentoring team members

Must-Have Qualifications

If you don't think you meet all of the criteria below but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team.

  • 3-5 years experience in IT Support or IT Operations in a professional environment
  • Experience with support ticket management and tracking
  • Outstanding communication and interpersonal skills, customer service, problem solving and collaboration abilities
  • Extensive technical knowledge of Mac OS, Windows, iOS and Android
  • Knowledge of endpoint management tools and practices (JAMF)
  • Familiar with common access/authentication systems and tools (Okta)
  • Experience with G Suite for Business (Gmail, GCal, GDocs, etc)
  • Ability to be on-call and work outside of business hours during urgent or maintenance situations
  • Some heavy lifting required

Nice-to-Have Qualifications

  • Experience with the following systems - Zendesk, G Suite for Business, Okta, Active Directory, Office 365, Zoom, Slack, Jira, Confluence, Azure AD, Microsoft Intune
  • Knowledge of video conferencing solutions and support
  • Network fundamentals and support experience (WiFi, VPN, printing)
  • IT related degree or relevant certifications
  • Experience working as a member of a multi-office IT team
  • A good sense of humor!

More About Us

Thumbtack is a local services marketplace – one of the largest in the U.S. – that helps millions of people hire local professionals. With hundreds of unique service categories, customers can find a Thumbtack pro for almost anything: landscapers, DJs, personal trainers, even piano teachers. And in making these connections, we empower local pros too. Helping them get new customers and make a living doing what they’re great at.

Founded in 2008 and headquartered in San Francisco, Thumbtack is backed by over $400 million in investment from Sequoia Capital, CapitalG, Tiger Global Management, Javelin Investment Partners and Baillie Gifford.

Thumbtack is proud to be an equal opportunity workplace committed to building a team culture that celebrates diversity, equity and inclusion.