Careers

Careers At Upside

We are always looking for great people to join our dynamic team.

Customer Success Manager

We are seeking a proactive and client-focused Customer Success Manager to join our growing team. This role serves as the primary relationship manager for our clients, ensuring they receive maximum value from our IT and cybersecurity services. You will act as the bridge between clients and technical teams, driving satisfaction, retention, and long-term partnerships.

Systems Administrator

We are seeking a reliable and technically skilled Systems Administrator to join our team. This role is responsible for maintaining, supporting, and optimizing our clients’ IT infrastructure, including servers, endpoints, cloud environments, backups, and core business systems.

Cybersecurity Sales Specialist (Remote – Winnipeg, MB)

We are seeking a driven Cybersecurity Sales Specialist at Upside to build pipeline, lead the full sales cycle, and close high-value deals, helping SMBs secure their businesses with cutting-edge cybersecurity solutions.

Network Security Specialist

We are hiring a Network Security Specialist at Upside to design, implement, and manage secure network systems, conduct vulnerability assessments, and respond to security breaches.