Experienced MSP/MSSP technologist | Systems, cybersecurity and AI-enabled operations
Calgary, Alberta — hybrid/remote with regular customer-site attendance
Full-time, permanent Falcon employee
CAD $80,000–$95,000 per year
Offers within the range will reflect the depth and relevance of demonstrated experience, technical breadth, security and AI judgment, project ownership, and readiness to contribute independently. The upper end is intended for candidates who demonstrate strong capability across most of the role’s core requirements.
The opportunity
Falcon Systems is a Calgary-based, cybersecurity-first technology company serving organizations across Canada. Managed IT and managed security are foundational capabilities for us, but they are not our ceiling. We combine MSP/MSSP delivery with commercial AI solutions, agentic operations, and customer transformation work.
We are looking for an experienced MSP/MSSP technologist who wants to own challenging work, grow across systems, cybersecurity and AI, and help shape the next stage of a forward-thinking Canadian provider. The successful candidate will independently own complex operational escalations, deliver bounded technical projects, implement cybersecurity controls, and represent Falcon professionally with customers.
This is an experienced, hands-on role for someone who can independently own complex operational work and selected technical projects while recognizing when risk, authority, or business impact requires escalation. You will move between Microsoft cloud services, endpoints, identity, networking, cybersecurity, customer sites, projects, and AI-enabled operations. This is neither an entry-level support position nor a detached architecture role.
Why Falcon?
Falcon offers a rare combination: we are established enough to deliver serious managed technology, cybersecurity, and AI services across Canada, yet small enough that strong people can see and shape the results of their work.
Larger providers can offer scale, but technical roles can become narrow, highly segmented, or separated from decision-makers by multiple layers of process. At Falcon, you will work closer to customers, leadership, technical decisions, and business outcomes. You will have opportunities to contribute across systems, cybersecurity, projects, service improvement, customer transformation, and AI-enabled operations rather than being permanently confined to one queue or product silo.
Falcon is firmly pro-AI, but not casually so. We have several years of commercial AI experience, operate our own internal AI operating system, and are actively moving from agentic execution toward governed autonomy. You will not be joining a company that is still debating whether AI matters. You will help determine how it is used safely, effectively, and commercially.
You will receive broad technical exposure, direct access to decision-makers, approved learning time, access to a broad technical and professional training catalogue through a preferred channel vendor, and room to earn broader responsibility as Falcon grows. You will have the opportunity to develop capabilities that are difficult to gain in a narrowly defined enterprise or large-provider role.
Less bureaucracy does not mean less discipline. Falcon expects accountability, sound judgment, documentation, security, customer care, and verified execution. The difference is that good ideas and capable people have a shorter path to meaningful impact.
Technical ability is necessary, but it is not enough. Character, judgment, coachability, and alignment with Falcon’s core values are central to this role. We want someone who communicates honestly, including about mistakes and uncertainty; protects customers and confidential information; takes ownership when work becomes difficult; treats people with respect; raises risk early; responds constructively to correction; and follows commitments through to verified closure.
What you will do
- Own complex operational issues through verified resolution or clean, evidence-backed escalation.
- Deploy, Manage, Administer and Diagnose Microsoft 365, Azure, AVD, Sharepoint Online, Teams, Entra ID, Exchange Online, Intune, Windows endpoint, identity, application, server, and connectivity issues.
- Keep customers and internal owners informed about status, risk, dependencies, and next-update timing.
- Perform approved onboarding, offboarding, licensing, and permission work.
- Deploy, Manage, Administer and Diagnose Firewall, Wi-Fi, VPN, switching, connectivity, and common Windows Server and Active Directory problems.
- Help deliver and operate Falcon’s full-stack cybersecurity program across 24/7 SOC and threat detection, endpoint and network monitoring, identity and email security, backup and business continuity, staff education, security reviews, AI governance, and proactive technical care.
- Execute documented customer onboarding and security-hardening plays, including assessment, data intake, documentation, baseline protection, Microsoft 365 hardening, EDR/SOC activation, Conditional Access, email authentication, password management, MDM, security-awareness training, incident-response readiness, and QBR preparation.
- Run Falcon’s operational cybersecurity playbooks from alert intake through verified closure: correlate evidence across identity, endpoint, EDR/MDR, managed SOC, email, network, and backup systems; assess scope, severity, and business impact; preserve evidence; perform authorized containment and remediation; coordinate customer and vendor communication; validate recovery; document the outcome; and feed lessons back into controls and runbooks.
- Implement and support endpoint protection, EDR/MDR, managed SOC, Microsoft security, secure access, backup, and security-awareness services.
- Escalate material incidents, broad containment decisions, forensic conclusions, and customer risk decisions with clear evidence and a specific decision request.
- Own selected onboarding, deployment, migration, modernization, and remediation workstreams under approved scope and design.
- Build implementation plans with milestones, dependencies, risks, rollback procedures, and acceptance criteria.
- Perform planned onsite assessments, troubleshooting, installations, and inventory verification.
- Travel within Canada when required for planned customer projects, assessments, deployments, conferences, or other approved commitments.
- Complete verification, documentation, handoff, and customer confirmation before calling work finished.
AI at Falcon
AI is not a side experiment at Falcon. We have several years of commercial AI experience and operate our own internal AI operating system. Our environment combines large frontier models with private and local AI where security, privacy, control, or workload requirements call for it.
We describe AI maturity in four stages:
- Assistive AI: Drafting, research, and individual assistance.
- AI-enabled automation: Repeatable tasks, integrations, workflow automation, and RPA.
- Agentic execution: Coordinated agents completing multi-step work under defined boundaries.
- Governed autonomy: Approved work completed with monitoring, evidence, exception handling, and human control over consequential decisions.
Falcon operates between stages three and four. The successful candidate will help:
- Improve agents, automations, runbooks, evaluations, approval controls, and safeguards.
- Connect AI safely to Microsoft 365, cybersecurity, and service-delivery systems.
- Support customer AI readiness and controlled transformation.
- Turn proven internal capabilities into secure, supportable commercial solutions.
You do not need to be a machine-learning researcher. You do need strong systems and security foundations, curiosity, structured problem-solving, responsible AI judgment, and the drive to learn.
What you bring
Required
- Approximately five or more years of progressive, hands-on IT experience; demonstrated ownership matters more than a strict year count.
- Post-secondary education or recognized technical training in information technology, computer systems, networking, cybersecurity, or a related discipline, or an equivalent combination of relevant professional experience and certifications.
- Independent troubleshooting experience across Microsoft 365, Windows endpoints, identity, applications, and common infrastructure.
- Experience owning escalations and bounded projects, deployments, migrations, or customer onboarding work.
- Practical networking, cybersecurity, change-risk, and escalation judgment.
- Experience implementing security controls, gathering evidence, or completing technical remediation.
- Strong written and verbal communication with technical and non-technical people.
- Reliable ticket, time, documentation, prioritization, and customer-closure habits.
- Professional composure, accountability, and respectful judgment under pressure.
- Responsible professional AI use with independent validation, or credible policy-driven non-use under a previous employer and the ability to adopt Falcon-approved practices safely.
- Eligibility to work in Canada.
- Ability to attend Falcon and customer sites throughout Calgary reliably.
- A valid driver’s licence and reliable transportation.
- Ability and willingness to travel occasionally within Canada, including overnight when required for planned work.
- Availability for occasional planned after-hours implementations.
Strongly preferred
- MSP/MSSP, IT service-provider, or multi-tenant experience.
- Role-relevant Microsoft, cybersecurity, networking, Ai or comparable technical certification.
- Microsoft 365 migrations, Entra ID, Conditional Access, Intune, Defender, Exchange Online, SharePoint, or Teams.
- Experience with PSA, RMM, EDR/MDR, managed SOC, backup, and documentation platforms.
- Hands-on cybersecurity operations and hardening across Microsoft 365 and Entra identity controls, MFA and Conditional Access, Intune and endpoint security, EDR/MDR and managed SOC services, email and phishing protection, secure access, network and firewall controls, vulnerability and patch remediation, backup and recovery validation, and security-awareness services.
- Practical incident-support experience: triaging security alerts, preserving evidence, assessing scope and risk, executing approved containment and remediation, validating recovery, documenting actions, communicating clearly with customers, and escalating consequential decisions appropriately.
- Ubiquiti UniFi, Fortinet, Meraki, Sophos, or comparable networking experience.
- Windows Server, Active Directory, virtualization, or 3CX/comparable business voice experience.
- PowerShell, Microsoft Graph, APIs, workflow automation, RPA, or agentic systems.
- Hands-on experience building, configuring, or extending personal AI assistants, agentic workflows, or AI-enabled applications; practical software-development interest or experience is a strong asset.
- Experience selecting between hosted frontier models and private/local AI for security, privacy, or operational reasons.
- Additional Microsoft, cybersecurity, networking, automation, or responsible-AI training and certifications, especially when supported by practical delivery experience.
Comparable-platform experience is welcome. We value demonstrated capability, judgment, and customer service over collecting product acronyms.
Character and values in action
Falcon’s core values are not wall decorations. They describe how we expect people to work when customers are frustrated, systems are failing, priorities conflict, or a mistake has been made.
- Accountability: Own commitments, outcomes, and mistakes. Communicate early when work is blocked and follow through without needing to be chased.
- Execution: Move important work forward, verify the result, and finish the documentation, handoff, and customer closure.
- Communication: Listen carefully, explain clearly, and surface risk, uncertainty, bad news, and changing timelines early.
- Teamwork: Share knowledge, ask for help when needed, and strengthen the team rather than becoming a hero bottleneck.
- Efficiency: Use good systems, automation, and AI to reduce rework without sacrificing judgment, security, or quality.
- Care: Protect customers, teammates, relationships, confidential information, and the quality of Falcon’s work.
- Courage: Raise concerns, challenge unsafe or ineffective approaches constructively, and make the right escalation even when it is uncomfortable.
- Growth: Stay curious, seek feedback, respond well to correction, and turn new knowledge into better decisions and outcomes.
We look for evidence of integrity, ownership, sound judgment, respectful communication, willingness to acknowledge mistakes, and the ability to learn and improve. We do not confuse character with charisma, confidence, a particular personality type, or similarity to the current team.
This role will suit someone who enjoys broad hands-on work, customer interaction, technical depth, responsible experimentation, and continuous learning.
It will not suit someone seeking exclusively remote work or avoiding practical endpoint and onsite responsibilities. It also requires someone who treats accountability, documentation, confidentiality, feedback, and follow-through as essential parts of the job.
How we hire
Falcon uses a structured, job-relevant selection process. Shortlisted candidates complete a structured interview and a standardized practical using synthetic evidence.
We assess character and values through specific examples, observed decisions in the practical, consistent questions, and job-relevant reference checks. We do not score candidates based on charisma, accent, appearance, video presentation, personality labels, or subjective “culture fit.”
We will also ask why you want to join Falcon specifically and what you hope to build, learn, or contribute here. We are looking for an informed connection to the actual opportunity, not flattery or rehearsed enthusiasm.
The practical evaluates troubleshooting, prioritization, customer communication, escalation, project planning, and safe AI use. It requires no personal paid AI account or access to real customer systems.
Falcon may use AI-assisted tools to organize job-related application evidence and support human review. Falcon personnel make all material hiring decisions. We do not use AI to make autonomous hiring decisions or infer personality or protected characteristics.
Falcon welcomes requests for reasonable accommodation during the selection process.
Want to stand out? Show us applied AI work
During the application, you will be invited to describe an AI-enabled project or workflow you personally worked on. It may involve assistive AI, automation, RPA, agents, system integrations, private or local models, or governed autonomous execution.
Strong examples explain:
- The problem or opportunity.
- What you personally designed, built, configured, or improved.
- The models, tools, integrations, or automation involved.
- How you protected sensitive information.
- Where human approval or oversight remained.
- How you tested and validated the result.
- What failed, changed, or required correction.
- The operational or customer outcome.
If a previous employer restricted AI use, say so honestly. You may instead explain how you would safely advance a synthetic workflow from AI assistance toward agentic execution. Respecting an employer’s security or acceptable-use policy will not count against you.
You may reference a public project or provide a sanitized diagram or screenshot, but this is not required. Do not submit passwords, source code owned by an employer, customer information, production data, or other confidential material.
How to apply
Submit your résumé and answers through Indeed Apply. Do not include passwords, customer-confidential information, production data, or other restricted material in your résumé or examples.
Questions or accommodation requests may be directed to [email protected].
Pay: $80,000.00-$95,000.00 per year
Application question(s):
- Calgary onsite requirement Are you currently located in the Calgary area, or able to relocate before your start date, and able to attend customer sites regularly?
- How much professional experience do you have working directly for an MSP, MSSP, IT service provider, or similar multi-customer technology organization?
- Which PSA, RMM, remote-support, and technical-documentation platforms have you personally used? Briefly explain how you used them—for example, ticket and time management, alert response, monitoring, patching, scripting, automation, endpoint remediation, reporting, or documentation.
Please distinguish platforms you operated hands-on from those you only observed or worked alongside.
- Describe the cybersecurity technology stack you have personally operated or supported. This may include identity and email security, MFA and Conditional Access, endpoint protection, EDR/MDR, managed SOC, vulnerability and patch remediation, firewalls and secure access, backup and recovery, security awareness, or incident-response tools.
Identify the products or comparable platforms you used and distinguish between work you personally performed, work you supported, and work you escalated to another team.
- Describe one technical project, migration, customer onboarding, deployment, or remediation workstream that you personally led or owned through closure.
What was your responsibility? How did you manage scope, milestones, dependencies, risk, rollback, communication, testing, documentation, handoff, and final acceptance? What was the outcome?
Do not include customer-confidential information, credentials, production data, or employer-owned restricted material.
- Describe the most advanced professional AI-enabled project or workflow you have personally built, configured, improved, or operated. It may involve AI assistants, automation, RPA, agents, integrations, private or local models, or governed autonomous execution.
Explain the problem, your personal contribution, information boundaries, validation, human approval points, corrections, and outcome.
If a previous employer restricted AI use, state that honestly and explain how you would safely advance a synthetic workflow from AI assistance toward agentic execution.
- Have you personally used both a PSA and an RMM platform in a production MSP, MSSP, or IT service environment? Answer Yes or No and name the PSA and RMM platforms you used.
- Work authorization Are you legally eligible to work in Canada for Falcon Systems without Falcon sponsoring a work permit?
Work Location: Hybrid remote in Calgary, AB
