Senior IT & SaaS Support Specialist (Contractor)

Remote Position
Port Moody, British Columbia, Canada. Contract . August 8, 2025

About Redstamp

Welcome to Redstamp, where creative strategy meets operational excellence. This role sits at the intersection of Redstamp and our innovation engine, GoodOps, a specialized arm of our business focused on helping teams scale through smart systems, automation, and AI.

As a Senior IT & SaaS Support Specialist, you’ll be the go-to technical resource helping our clients troubleshoot issues, configure modern SaaS tools, and keep their systems running smoothly. You’ll work alongside a curious and collaborative team of operations consultants, automation specialists, and tech-forward creatives to support remote-first teams in managing devices, securing accounts, and getting the most out of tools like Google Workspace, Microsoft 365, Slack, and more.

At Redstamp, our clients are largely SaaS companies looking for creative partners who help them enhance their brands and expand their reach. We are proud of our long-term client relationships with marketing leaders who call us to support them and their teams time after time.

Redstamp was founded in 2011 by Kelso Kennedy and Spencer Ririe. These two awesome and creatively passionate people lead a team of developers, designers, marketers, and more. Redstampers (That’s what we call ourselves :D) embody our CRFT values, we are all: #curious #resourceful #fair #tenacious.

We believe that thoughtful systems design is just as creative as visual design and that great operations can elevate every part of a business. If that sounds like your kind of work, we’d love to hear from you.

What You’ll Do

As a Senior IT & SaaS Support Specialist, you will:

• Serve as a technical support lead for client tickets related to devices, apps, and infrastructure
• Troubleshoot and resolve issues related to email, networks, file sharing, device security, and user access
• Support SaaS onboarding, configuration, and troubleshooting (Google Workspace, Notion, Slack, Airtable, etc.)
• Escalate and manage critical incidents with vendors and internal teams
• Advise clients on best practices for tool setup, permissions, and integrations
• Contribute to internal knowledge base and documentation
• Help clients adapt tools to their workflows (you understand both product and process)

Tools You Should Know

• Google Workspace administration (Gmail, Drive, Groups, IAM)
• Device management tools (e.g., JumpCloud, Intune, Mosyle, or similar)
• SaaS platforms (Slack, Notion, Airtable, Zoom, Microsoft 365)
• Ticketing systems (e.g., Synchro, HaloPSA, Zendesk)
• Optional: Automation tools like Zapier, Make, or scripting for troubleshooting

Must-Have Skills

• 3+ years of experience in IT support or MSP environments
• Strong troubleshooting skills across both Windows and macOS
• Familiarity with SaaS tools and ability to guide non-technical users
• Confident working directly with clients, via email and video calls
• Able to manage multiple small clients and keep detailed records
• Clear communicator with a calm, problem-solving mindset

Bonus (Nice-to-Have)

• Experience with Synchro or HaloPSA
• Light scripting experience (Bash, PowerShell, Python)
• Familiarity with identity and access control (SSO, MFA setup)
• Experience supporting fully remote or hybrid teams

Our Commitment to Inclusion

Redstamp welcomes all applicants regardless of race, gender, orientation, sexual identity, economic class, ability, disability, age, religious beliefs or disbeliefs, or status. We believe that different perspectives and backgrounds are what make a company flourish and we welcome you!  Our team is diverse and geographically distributed across Canada and around the world. This opportunity is only open to candidates within Canada at this time.

If all of this resonates with you, please apply by September 12, 2025. We can’t wait to meet you!

Compensation

$50.00 - $80.00 per hour

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