A tailored course, built for your situation
Modern Security Awareness Programs for Mid-Market Operations
Implementation-grade training for security and operations leaders building resilient, people-first programs
$199 one-time
24-hour access provisioning
30-day money-back guarantee
Hand-built implementation playbook
12 modules. 12 chapters per module. 144 chapters total.
12 modules, each with 12 chapters (144 chapters total), text-based, plus downloadable templates and a hand-built implementation playbook delivered alongside course access.
Security awareness programs that feel like check-the-box exercises fail to change behavior or reduce risk.
The situation this course is for
Mid-market teams often inherit enterprise templates or under-invested campaigns that don’t fit their pace, culture, or compliance needs. This leads to low engagement, audit findings, and reactive fixes instead of proactive resilience. Meanwhile, leadership expects measurable outcomes without clear ownership or resources.
Who this is for
Security leads, risk officers, compliance managers, and technology leaders in mid-market organizations (200, 2,000 employees) who own or influence security culture initiatives.
Who this is not for
Enterprise-level security directors with mature, staffed awareness teams, or individuals seeking certification prep or technical penetration testing skills.
What you walk away with
- Design a security awareness program aligned to organizational risk posture and operational tempo
- Develop role-specific training tracks that reduce fatigue and increase retention
- Implement measurable phishing and social engineering simulation cycles
- Engage leadership with data-driven progress reports and risk reduction narratives
- Integrate awareness outcomes into compliance and audit workflows
The 12 modules (with all 144 chapters)
Module 1. Foundations of Modern Security Awareness
Defining scope, success, and stakeholder alignment for mid-market contexts.
12 chapters in this module
- Defining security awareness in operational terms
- Mapping regulatory and compliance drivers
- Assessing current program maturity
- Identifying core stakeholders and sponsors
- Setting realistic behavioral goals
- Establishing baseline metrics
- Aligning with organizational culture
- Avoiding common enterprise misfits
- Budgeting for impact, not just coverage
- Creating the program charter
- Choosing delivery cadence
- Documenting assumptions and constraints
Module 2. Audience Segmentation and Role Design
Tailoring content and delivery by function, privilege, and risk exposure.
12 chapters in this module
- Identifying high-risk roles
- Segmenting by data access level
- Mapping job functions to threat models
- Designing for finance teams
- Designing for HR teams
- Designing for engineering teams
- Designing for executive assistants
- Designing for remote and hybrid workers
- Accounting for tenure and onboarding timing
- Building personas with real data
- Validating segmentation with managers
- Updating segmentation quarterly
Module 3. Content Strategy and Message Design
Creating relevant, memorable, and non-punitive messaging.
12 chapters in this module
- Crafting positive security narratives
- Avoiding fear-based messaging
- Using storytelling frameworks
- Designing for mobile-first consumption
- Writing concise, actionable takeaways
- Localizing language and examples
- Incorporating real incidents (anonymized)
- Balancing compliance and culture
- Scheduling by operational calendar
- Testing message clarity
- Using humor without trivializing risk
- Versioning content for repeat exposure
Module 4. Phishing Simulation Design
Running ethical, educational, and effective simulations.
12 chapters in this module
- Setting simulation goals
- Choosing frequency and scope
- Designing realistic attack scenarios
- Avoiding user shaming
- Tracking click and report rates
- Providing immediate feedback
- Escalating follow-up training
- Involving legal and HR appropriately
- Reporting simulation outcomes
- Adjusting difficulty over time
- Benchmarking against peers
- Documenting simulation ethics policy
Module 5. Leadership Engagement and Advocacy
Securing visible buy-in and participation from executives.
12 chapters in this module
- Identifying executive champions
- Educating leaders on their role
- Designing executive-specific content
- Involving execs in simulation cycles
- Reporting to leadership quarterly
- Tying awareness to strategic goals
- Celebrating leadership participation
- Handling executive failures gracefully
- Creating board-level summaries
- Integrating with executive onboarding
- Leveraging all-hands meetings
- Measuring leadership influence
Module 6. Metrics That Matter
Moving beyond completion rates to behavioral and business impact.
12 chapters in this module
- Choosing leading vs. lagging indicators
- Tracking behavior change over time
- Measuring reporting rates
- Calculating mean time to report
- Linking training to incident trends
- Benchmarking against industry norms
- Avoiding vanity metrics
- Creating dashboards for different audiences
- Using data to justify budget
- Auditing metric accuracy
- Sharing wins without oversharing risk
- Revising KPIs annually
Module 7. Compliance Integration
Aligning awareness with audit requirements and control frameworks.
12 chapters in this module
- Mapping to ISO 27001 controls
- Meeting NIST SP 800-50 expectations
- Supporting SOC 2 Type II audits
- Documenting employee attestations
- Archiving training records
- Aligning with GDPR and CCPA training mandates
- Integrating with third-party risk assessments
- Preparing for regulatory interviews
- Demonstrating continuous improvement
- Linking to policy acceptance workflows
- Generating auditor-ready reports
- Updating content for new regulations
Module 8. Behavioral Reinforcement
Building habits through repetition, recognition, and nudge design.
12 chapters in this module
- Applying behavioral psychology principles
- Designing recognition programs
- Using positive reinforcement effectively
- Creating 'security champion' networks
- Incentivizing reporting
- Gamifying responsibly
- Incorporating microlearning
- Using email and Slack nudges
- Timing reminders post-incident
- Measuring habit formation
- Avoiding burnout and fatigue
- Refreshing reinforcement tactics
Module 9. Crisis Response Integration
Connecting awareness to incident response playbooks.
12 chapters in this module
- Educating teams on escalation paths
- Teaching how to recognize incident phases
- Training on communication protocols
- Simulating internal reporting
- Reducing time to first report
- Coordinating with IR teams
- Updating playbooks based on feedback
- Running tabletop exercises
- Involving comms and legal early
- Measuring response readiness
- Post-incident communication templates
- Learning from near-misses
Module 10. Technology Enablement
Selecting and configuring tools to scale delivery and measurement.
12 chapters in this module
- Evaluating awareness platforms
- Integrating with identity providers
- Automating assignment rules
- Using APIs for data syncing
- Configuring analytics dashboards
- Setting up auto-remediation paths
- Managing vendor relationships
- Pilot testing new features
- Ensuring accessibility standards
- Planning for mobile access
- Auditing platform usage logs
- Budgeting for SaaS renewals
Module 11. Program Sustainability
Planning for longevity, refresh cycles, and ownership transitions.
12 chapters in this module
- Defining program ownership
- Creating documentation repositories
- Planning for staff turnover
- Establishing review cadences
- Updating content for new threats
- Rotating content themes annually
- Securing multi-year funding
- Measuring long-term engagement
- Conducting annual program audits
- Soliciting stakeholder feedback
- Scaling with organizational growth
- Archiving outdated materials
Module 12. Advanced Engagement Models
Evolving from compliance-driven to culture-driven programs.
12 chapters in this module
- Building internal security communities
- Launching ambassador programs
- Hosting security awareness events
- Integrating with onboarding
- Linking to performance reviews
- Partnering with L&D teams
- Creating internal campaigns
- Using internal influencers
- Measuring cultural shift
- Sharing cross-functional wins
- Aligning with ESG goals
- Publishing annual security culture reports
How this maps to your situation
- Onboarding a new security awareness platform
- Facing an upcoming compliance audit
- Responding to increased phishing incidents
- Scaling operations across regions
Before vs. after
Before
Security awareness feels like a checkbox exercise with low engagement and unclear ROI.
After
The program drives measurable behavior change, supports compliance, and strengthens organizational resilience.
What's included with your purchase
- 12 modules with 12 chapters each (144 chapters)
- Downloadable templates and worked examples for every module
- Hand-built implementation playbook delivered alongside course access
- 30-day money-back guarantee
Delivery and format
- Course and learning environment access provisioned within 24 hours of purchase
- Hand-built implementation playbook delivered alongside course access
Format: Text-based modules and chapters in the Art of Service learning environment, plus downloadable templates and worked examples for every chapter, plus the hand-built implementation playbook delivered alongside course access.
Time investment: Approximately 4, 6 hours per module, designed for self-paced learning with implementation milestones.
If nothing changes
Continuing with ad-hoc or outdated awareness approaches risks audit failures, repeated incidents, and erosion of trust during crises, while missing the chance to build a proactive security culture.
How this compares to the alternatives
Unlike generic certification prep or enterprise-focused playbooks, this course delivers targeted, implementation-ready guidance for mid-market teams balancing limited resources with growing compliance and threat demands.
Frequently asked
Who is this course designed for?
Security, risk, compliance, and technology leaders in mid-market organizations building or improving security awareness programs.
How is the course structured?
12 modules, each containing 12 chapters (144 chapters total).
Is there a money-back guarantee?
Yes, we offer a 30-day money-back guarantee if the course doesn’t meet your expectations.
$199 one-time. Approximately 4, 6 hours per module, designed for self-paced learning with implementation milestones..
Within 24 hours your account in the learning environment is provisioned and the tailored implementation playbook is delivered alongside it.
30-day money-back guarantee·
144 chapters·
Hand-built playbook included·
Account access within 24 hours