IT Specialist (Intermediate/Senior)

This is an opportunity in the exciting and fast-growing transportation technology industry. Public transit is being transformed from a system of static, scheduled fixed-routes, to a dynamic on-demand network, and you will be one of the pioneers shaping this transformation.

As an Intermediate/Senior IT Specialist, you will play a critical role in shaping and scaling the company’s IT infrastructure, security posture, and operational excellence. This role requires expertise across systems administration, networking, and information security along with the ability to translate complex technical requirements into scalable, secure, and business-aligned solutions. You will thrive in a small-team environment, moving at a fast pace, where every team member contributes solutions that deliver a meaningful impact to our employees and the company.

Your day-to-day responsibilities will include:

IT Infrastructure & Systems Leadership

• Own and evolve IT standards, architecture, and best practices across a mixed OS environment (Windows, Linux, Mac, Mobile Devices)
• Contribute to the design, implementation, and optimization of centralized identity and access management systems (e.g., Active Directory, LDAP)
• Contribute to and maintain scalable, secure, and highly available infrastructure across on-premises and cloud environments

Network Architecture & Security

• Oversee the company’s corporate network, including segmentation, subnetting, VPNs, WiFi, and secure remote access
• Contribute to network security strategy, including intrusion detection, endpoint protection, and zero-trust principles
• Drive ongoing improvements to security posture, ensuring alignment with industry best practices and compliance requirements

Cloud & Platform Operations

• Oversee third-party SaaS platforms (e.g., Google Workspace, Salesforce, Dropbox), including licensing, configuration, and access controls
• Ensure systems are highly available, performant, and cost-efficient

Device & Endpoint Management

• Own end-to-end lifecycle management of hardware and mobile devices, including procurement, provisioning, MDM governance, and asset tracking
• Establish scalable, secure, and repeatable processes for device configuration and deployment
• Continuously evaluate and improve endpoint management strategies

Operational Excellence & Support Leadership

• Serve as a senior escalation point for complex technical issues across hardware, software, and network systems
• Lead incident response and root cause analysis efforts, driving long-term solutions
• Manage vendor relationships and third-party service providers to ensure service quality and performance

Security, Compliance & Risk Management

• Contribute to enforcement of company-wide information security policies and controls
• Conduct regular security audits, risk assessments, and vulnerability reviews
• Conduct backup, disaster recovery, and business continuity planning

Strategy, Mentorship & Cross-Functional Collaboration

• Contribute to strategic direction on IT roadmap, infrastructure investments, and scaling initiatives
• Partner with Engineering, Product, and Operations teams to align IT systems with business needs
• Contribute to budgeting, forecasting, and cost optimization initiatives

Project Leadership & Continuous Improvement

• Lead complex IT projects from planning through execution, ensuring timely and high-quality delivery
• Develop and maintain documentation, SOPs, and automation frameworks
• Drive continuous improvement across systems, processes, and tooling

Additional Responsibilities

• Participate in occasional off-hours support for critical systems and deployments
• Other duties and strategic initiatives as assigned

Qualifications & Experience:

Required

• Degree or diploma in IT, Computer Science, DevOps, or related field
• 5+ years of progressive experience in IT and systems administration
• Proven experience designing and scaling secure IT infrastructure and networks
• Experience in networking, security, and systems architecture
• Strong problem-solving skills with the ability to operate independently in complex environments
• Experience implementing and managing centralized identity systems (e.g., Active Directory, LDAP)
• Experience building and supporting distributed environments with remote employees
• Strong communication skills with both technical and non-technical stakeholders
• Demonstrated leadership, mentorship, and project ownership experience

Preferred

• Experience with LDAP technologies (OpenLDAP, Microsoft Active Directory)
• Experience managing Windows and Linux servers (Debian/Ubuntu)
• Familiarity with Security and Privacy Compliance programs (NIST, SOC2, HIPAA, GDPR)
• Knowledge of scripting and automation
• Familiarity with cloud infrastructure (AWS, EC2, RDS, Terraform)
• Experience with MDM platforms and endpoint security tools
• Passion for learning and adopting new technologies

Compensation and Benefits:

• Base Salary: $75k - $100k + performance-based bonus + stock options
• Work-Life Balance & Additional Perks: Flex-time work schedules, vacation time, bi-weekly catered lunches, social events, casual dress code
• Benefits Plan: Medical, dental, prescription, life/health spending accounts and more
• Work Environment: Located in KW's most desirable work space in the heart of Uptown Waterloo
• Commuter Program: Complimentary rides to and from work in Waterloo Region