Cyber Awareness Specialist

Benjamin Olenick

Phishing simulations  ·  Awareness campaigns  ·  Security training  ·  Behavioural metrics

50K+ Employees reached
31 → 4% Click rate at BMO
83% Compromise reduction
10+ Years enterprise security
cyberaware-ai // interactive
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Results

BMO Financial Group — 50,000+ Employees
31 → 4.1%
Phishing click rate reduction enterprise-wide over 18 months. Highest behavior-change improvement in the program's recorded history. Zero phishing-attributed account compromises in the 12 months following program maturity, down from 14 confirmed incidents the prior year.
Phishing Simulation
Ritchie Bros. (RB Global) — Global Operations
83%
Reduction in phishing-origin credential compromises year-over-year through predictive awareness targeting. High-risk user click rate dropped 71% over two years of sustained simulation and targeted training intervention across North America, Europe, and Asia-Pacific.
Predictive Targeting
Rexig Realty — 80+ Staff
23 → 6%
Click rate reduced from 23% to under 6% across four simulation cycles. Zero successful social engineering attacks against staff in the 18 months following program launch, including during two targeted credential-harvest campaigns observed in the wild against the real estate sector.
Awareness Campaigns

Programs

BMO Financial Group
Cyber Security Analyst
Oct 2018 – Oct 2020

Enterprise Phishing Simulation & Awareness Curriculum

  • Built the enterprise phishing simulation program from scratch for 50,000+ employees: vendor evaluation, platform procurement, template library development, multi-wave campaign cadencing, and CISO-level reporting.
  • Designed and delivered the companion security awareness training curriculum: role-based content tracks by business function and risk tier, new-hire onboarding stream, executive and privileged-user stream, and integration with simulation outcomes.
  • Completion metrics and behavior-change trends reported quarterly to the CISO organization; coordinated rollout with HR, Legal, Compliance, and all business unit leaders.
  • Automated simulation-to-training pipeline: click events enrolled users in targeted remediation modules within 24 hours; repeat offenders escalated to manager notification workflow.
Phishing Sim Curriculum Design CISO Reporting 50K Employees
Ritchie Bros. (RB Global)
Security Operations Lead
Mar 2021 – Feb 2023

Predictive Click-Risk Targeting & Global Awareness Program

  • Led and owned security awareness and phishing simulation across all global business units: template library, multi-wave campaign cadences, click-rate dashboards, and quarterly awareness reports for security leadership.
  • Developed a phishing click-likelihood predictive analytics pipeline that scored each employee's risk from historical simulation data, surfaced highest-risk cohorts to security leadership, and fed targeted training prioritization before incidents occurred.
  • Coordinated program rollout across North America, Europe, and Asia-Pacific with HR, IT, and regional business leads; produced regional risk comparison reports for the CISO.
Predictive Analytics Global Rollout Risk Scoring Stakeholder Alignment
Rexig Realty Inc.
IT Manager & Manager of Cybersecurity
Jan 2023 – Sept 2025

Full-Stack Awareness Program Under Dual IT/Security Mandate

  • Held dual accountability for the full IT function and cybersecurity program; designed and delivered phishing simulations, awareness campaigns, and continuous program reporting to ownership alongside managing infrastructure and IT operations.
  • Reduced employee phishing click rates from 23% to under 6% over four simulation cycles with targeted awareness interventions; zero successful social engineering attacks in the 18 months following program launch.
  • Built simulation-to-training funnel and awareness calendar; coordinated with leadership on policy updates and awareness messaging following industry incidents relevant to commercial real estate sector.
IT Manager Awareness Campaigns Policy Integration Executive Reporting

Spot the Phish

Four emails. Each has three red flags. Click what looks suspicious — this is exactly the skill I build into every awareness curriculum I design.

Email 1 of 4 Flags found: 0 / 12
Click the underlined text to identify red flags
This email: 0 / 3 flags found
0
out of 12 flags identified

Contact

Let's build your program.

Available for enterprise roles and consulting engagements focused on cyber awareness program design, phishing simulation, campaign strategy, and reporting. Open to Toronto hybrid and remote.

Available now
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