Manager Technology and AI
DependableIT Group Inc. | Job Description
Position Summary
DependableIT is seeking a hands-on Manager, Technology & AI to lead our internal IT function and support the continued growth of our technical services capabilities.
This individual will be accountable for the reliability, security, and continuous improvement of DIT's technology environment. The role will lead the IT team, oversee day-to-day technology operations, deliver infrastructure and development projects, and act as the senior technical escalation point for complex issues.
The successful candidate must be an advanced and practical user of artificial intelligence. They will be expected to use AI throughout their own work and identify opportunities to responsibly apply AI and automation across DIT's technology operations, internal processes, and client solutions.
This is a working manager position. The successful candidate must be comfortable setting direction, managing people and projects, communicating with leadership and clients, and contributing directly to technical work when required.
Key Responsibilities
IT Leadership and Team Management
- Lead, support and develop DIT's IT team, establishing clear priorities, responsibilities and performance expectations.
- Manage the allocation of work across operational support, infrastructure, security, development and project requirements.
- Establish effective escalation processes and serve as the senior technical escalation point.
- Develop the team's capabilities through coaching, cross-training, documentation and relevant technical certifications.
- Maintain appropriate coverage and succession plans for critical systems and responsibilities.
- Provide leadership with concise updates regarding performance, projects, risks, costs and required decisions.
- Take ownership of assigned initiatives and ensure work progresses between leadership meetings.
- Translate business requirements into practical technical plans, deliverables and recommendations.
IT Operations and Service Management
- Oversee the day-to-day operation of DIT's technology environment and internal IT support function.
- Establish and maintain service levels, ticket priorities, response expectations and escalation procedures.
- Monitor ticket volume, backlog, response time, resolution time, recurring issues and user experience.
- Manage Microsoft 365, identity and access, endpoints, hardware, software, connectivity and core business applications.
- Oversee employee technology onboarding, offboarding, equipment deployment and access changes.
- Maintain accurate inventories of hardware, software, licences, accounts, domains, certificates, warranties and technical ownership.
- Ensure technical processes, system configurations, procedures and recovery instructions are properly documented.
- Identify recurring issues and implement permanent solutions rather than relying on repeated manual intervention.
Infrastructure Network and Cloud Management
- Design, operate, secure and improve network, server, cloud and hybrid infrastructure across AWS, Azure and on-premises environments.
- Configure, maintain and troubleshoot firewalls, network connectivity, VPNs, segmentation and remote-access solutions.
- Lead the migration of appropriate remaining services from on-premises infrastructure to secure and cost-effective cloud environments.
- Monitor infrastructure capacity, availability, performance, reliability and cost.
- Identify opportunities to simplify the environment, reduce technical debt and eliminate unnecessary infrastructure or expenses.
- Use infrastructure-as-code, scripting and automation to improve consistency, efficiency and recoverability.
- Support environments that may require business-hours or 24/7 monitoring, alerting and escalation.
Cybersecurity and Risk Management
- Implement and maintain effective cybersecurity controls across DIT's technology environment.
- Manage identity and access controls, multifactor authentication, privileged access and least-privilege practices.
- Oversee endpoint protection, security monitoring, patching, vulnerability management and remediation.
- Assess the security and privacy implications of new applications, vendors, integrations and AI tools.
- Support client security reviews, questionnaires, audits, insurance requirements and requests for technical evidence.
- Maintain documented incident-response procedures and lead the technical response to security incidents.
- Complete root-cause analysis and post-incident reviews following significant security or technology events.
- Escalate material risks to leadership with clear recommendations, costs, and remediation plans.
Business Continuity Backup and Disaster Recovery
- Maintain DIT's technical business-continuity and disaster-recovery plans.
- Ensure backups are completed, monitored, protected and retained appropriately.
- Establish appropriate recovery-time and recovery-point objectives for critical systems.
- Conduct scheduled backup-restoration and disaster-recovery testing.
- Identify single points of failure and recommend appropriate mitigation.
- Maintain current system recovery procedures, dependency maps, and technical contacts.
- Report testing results, identified gaps, and remediation progress to leadership.
AI Enablement and Automation
- Lead the practical adoption of AI and automation within DIT's technology function.
- Use AI tools throughout development, troubleshooting, research, testing, documentation, architecture planning, and code review.
- Identify opportunities to apply AI across technical support, monitoring, incident triage, reporting, development, and internal workflows.
- Build or oversee AI-assisted workflows, internal agents, retrieval systems, integrations and automated processes.
- Evaluate emerging AI technologies and recommend adoption based on business value, accuracy, security, privacy and cost.
- Establish appropriate controls governing the use of confidential information, client data, source code, credentials and personal information with AI platforms.
- Ensure appropriate human review, access controls, logging and auditability are incorporated into AI-enabled processes.
- Train and support employees in the effective and responsible use of approved AI tools.
- Measure and report the results of AI initiatives, including time saved, work automated, costs reduced, and quality improvements.
Solutions Architecture and Development
- Translate business and client requirements into secure, scalable and maintainable technical solutions.
- Provide technical leadership for application development, system integrations, APIs, databases and modernization initiatives.
- Contribute directly to software development, scripting, integration or troubleshooting when required.
- Establish and maintain appropriate practices for source control, testing, code review, CI/CD, release management and production support.
- Ensure technical solutions include appropriate documentation, security, monitoring, support procedures and ownership.
- Prevent critical systems and applications from becoming dependent on undocumented knowledge held by a single employee.
- Support modern web, mobile and backend technologies based on project requirements rather than being limited to one specific development framework.
Project and Client Support
- Lead technical projects from requirements and planning through deployment, handoff and ongoing support.
- Define project scope, milestones, responsibilities, dependencies, risks and acceptance criteria.
- Provide regular and accurate project updates, including issues requiring leadership decisions.
- Coordinate testing, quality assurance, user acceptance, release planning and rollback procedures.
- Participate in client discovery, technical requirements gathering and solution-design discussions.
- Support proposals, RFP responses, estimates, demonstrations and statements of work.
- Assist in developing repeatable managed IT, cloud, monitoring, infrastructure, development and AI-enabled service offerings.
- Design appropriate monitoring, alerting, ticketing, escalation, reporting and service-level models.
- Ensure proposed client solutions are secure, supportable, appropriately staffed and commercially practical.
Vendor Licence and Cost Management
- Manage technology vendors, service providers, contracts, renewals and performance.
- Monitor and optimize cloud, telecommunications, software, hardware and infrastructure costs.
- Maintain visibility into technology spending and upcoming commitments.
- Review licence utilization and eliminate unnecessary or duplicative expenses.
- Evaluate new vendors and technologies based on capability, security, supportability, integration, and total cost.
- Develop recommendations and business cases for significant technology investments.
Required Qualifications
- Five or more years of progressive experience across IT infrastructure, cloud services, networking, systems administration, cybersecurity, or related technical functions.
- Previous experience leading employees, coordinating technical work, or acting as the senior owner of an IT environment.
- Demonstrated hands-on experience with Microsoft 365, identity and access management, endpoints, networks, servers and cloud infrastructure.
- Practical experience with AWS, Azure or comparable cloud platforms.
- Experience configuring, securing or troubleshooting enterprise firewalls, VPNs and network environments.
- Working knowledge of cybersecurity controls, vulnerability management, incident response, backups and disaster recovery.
- Experience delivering technical projects from requirements through implementation and operational handoff.
- Experience with scripting, automation, APIs, integrations, or software development.
- Demonstrated ability to use AI effectively for technical work, problem-solving, automation or software development.
- Ability to explain technical issues, options, and risks clearly to non-technical leaders and clients.
- Strong documentation, organization, prioritization, and follow-through.
- Ability and willingness to contribute directly to technical work while leading the broader function.
Preferred Qualifications
- Experience with Terraform or other infrastructure-as-code technologies.
- Experience developing or supporting CI/CD pipelines.
- Experience with JavaScript, TypeScript, Node.js, Python, Java, C#/.NET, SQL, or comparable technologies.
- Experience with React, Flutter, or other modern web or mobile development frameworks.
- Experience with PostgreSQL, SQL Server, Firebase, or other relational and cloud databases.
- Experience building AI-assisted workflows, agents, retrieval-augmented generation systems or model integrations.
- Familiarity with AI development tools such as Codex, Claude Code, Gemini CLI or comparable platforms.
- Experience with managed services, monitoring platforms, ticketing systems and automated incident routing.
- Experience supporting client discovery, solution design, proposals or technical pre-sales.
- Relevant Microsoft, AWS, Azure, Google Cloud, Cisco, Fortinet, Check Point, ITIL or cybersecurity certifications.
- Experience working within a contact-centre, managed-services, telecommunications or technology-services environment.
What Success Looks Like
Within the first 12 months, the successful candidate will have:
- Established clear ownership, priorities and operating expectations for the IT team.
- Improved service levels, escalation management and visibility into IT performance.
- Documented critical systems, infrastructure, applications, access requirements and recovery procedures.
- Reduced reliance on individual employees for critical technical knowledge.
- Identified and began addressing DIT's highest-priority cybersecurity and continuity risks.
- Demonstrated successful backup-restoration and disaster-recovery testing.
- Improved the reliability, security, and cost-effectiveness of DIT's infrastructure.
- Delivered assigned projects with clear scope, timelines, status reporting and operational handoff.
- Implemented practical AI and automation improvements with measurable business results.
- Supported the design and delivery of new internal or client-facing technical solutions.
- Developed a capable, accountable, and increasingly versatile IT team.
