Flight instructor Jobs in Calgary, AB

About the Role
This is a senior individual-contributor project management contract inside the Enterprise Security group of a major Canadian energy infrastructure organization, a function that brings physical security and cybersecurity under one roof. The portfolio spans a mix of in-flight initiatives being handed off and net-new work not yet fully scoped, with most projects in the $500K combined CapEx/OpEx range and a target completion window of year-end 2026. There are no direct reports; delivery runs through coordinated vendor and system integrator relationships managed from a procurement standpoint. The engagement runs to December 18, 2026, with a strong likelihood of extension into confirmed 2027 work. Two positions are open under this same posting, each with a distinct profile: one anchored in cybersecurity or penetration testing delivery (with GRC advisory experience as a meaningful differentiator), and one anchored in OCM or communications-led delivery, still with baseline security-adjacent project exposure. Submit toward whichever profile your candidate genuinely fits rather than attempting to cover both.

The right candidate has owned cybersecurity or security-adjacent project delivery directly, not just supported it, and can run an independent portfolio without a surrounding project management team. Strong communication skills and a collaborative working style are just as important as technical delivery credibility here. The hard disqualifier for both profiles is a project history confined to generic enterprise IT work with no cybersecurity or security-adjacent exposure anywhere in the job history. Candidates whose primary experience is managing other project managers rather than running their own delivery portfolio are also not a fit.

Key Responsibilities
1. Own an independent portfolio of cybersecurity and information security projects from initiation through close, including both in-flight handoffs and net-new scopes.
2. Coordinate delivery teams, vendors, and system integrators from a procurement standpoint, without relying on a supporting project management structure.
3. Drive penetration testing engagements and broader security program deliverables to year-end completion within defined budget parameters.
4. Maintain clear, consistent communication with stakeholders at all levels, translating technical security delivery into terms that resonate across the business.
5. Manage project financials across combined CapEx and OpEx budgets typically in the $500K range, tracking scope, schedule, and cost with rigor.
6. Apply GRC (governance, risk, and compliance) thinking to delivery decisions where relevant, surfacing risk early and keeping leadership informed.
7. Support change management or communications-led delivery workstreams (for the OCM profile position) while maintaining baseline security-adjacent project standards.
8. Contribute to a collaborative team culture inside a fast-paced, dual-mandate security function.

Required Skills & Experience

• 8 or more years of IT or technology project delivery experience (the department lead has confirmed that 8 to 9 years is within range for strong candidates, despite the posted 10-plus year bar).
• Direct, hands-on project delivery experience on cybersecurity, information security, or security-adjacent initiatives; general enterprise IT delivery without this exposure does not meet the bar for either profile.
• Demonstrated ability to run a delivery portfolio independently, including coordinating vendors and system integrators from a procurement standpoint, without a supporting project management team.
• No experience managing other project managers in lieu of owning delivery; both positions have no direct reports.
• Strong communication skills and a collaborative working style, evidenced in a fast-paced delivery environment.
• University degree in a relevant discipline.
• Legally entitled to work in Canada; sponsorship is not available.
• Every requirement above must be demonstrated through specific employers, projects, and deliverables in the candidate's job history; a skill listed in a technical skills section without corresponding job history does not satisfy the bar.

Preferred Skills

• GRC (governance, risk, and compliance) advisory background, particularly for the cybersecurity-profile position.
• PMP or PRINCE2 certification.
• OCM or communications-led delivery expertise, particularly for the second profile position, combined with baseline security-adjacent project exposure.