IT Specialist (Intermediate/Senior)

RideCo•Waterloo, ON

40d•Onsite

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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