How to Launch a Security Awareness Training Program in 90 Days

Most organizations don’t struggle to understand why security awareness training matters. They struggle to launch it in a way that actually changes behavior.

The common failure pattern looks like this: training gets purchased, a one-time assignment is sent out, people click through content, and then nothing changes. Employees still hesitate to report suspicious messages. Teams still get hit by urgent impersonation requests. And leadership still can’t answer the most important question: “Is our training reducing risk?”

A strong program flips that approach. Instead of treating awareness as a once-a-year checkbox, it treats awareness like an operational control - something that shapes day-to-day decisions. In practice, that means you do three things well:

1. Teach practical skills employees can apply immediately
2. Reinforce those skills through realistic practice (especially phishing simulations)
3. Measure outcomes so you can improve month over month

This guide shows you how to do all of that in 90 days using Cybrary’s Security Awareness Training (SAT).

Day 0–7: Define success, scope, and ownership

The first week is where speed is won or lost. The biggest reason awareness programs stall is that nobody defines what “success” means, who owns the program, or how progress will be measured.

Start by writing a short “program charter” you can share internally. Keep it simple. It should answer:

What risky behaviors are we trying to reduce?

Think about the incidents and near-misses that create the most damage: clicking suspicious links, entering credentials into fake login pages, approving payment changes without verification, mishandling sensitive data, or responding to urgent requests that bypass normal processes.

What safer behaviors are we trying to increase?

You want employees to pause when something feels off, verify requests through a second channel, and report suspicious activity quickly and confidently.

How will we prove progress?

Completion rates alone don’t tell you if your risk is going down. Your early scorecard should focus on measurable signals such as reporting volume, time-to-report, and performance in phishing simulations - because these are the behaviors that prevent incidents from escalating.

Next, assign ownership. Even if you’re a smaller company, it helps to define these roles clearly:

• Executive sponsor to reinforce priority and expectations
• Program owner to manage cadence, reporting, and improvement
• HR/internal communications partner to support tone and participation
• IT/helpdesk partner to support reporting expectations and response consistency

Finally, set your tone. The fastest way to undermine your program is to make people feel like they’ll be punished for mistakes. Employees who fear consequences don’t report - they hide. Your program should make one message crystal clear: reporting is always the right move, even when someone isn’t sure.

Day 8–14: Establish your baseline and segment your audience

Week two is about relevance and readiness. Training works when it mirrors the reality of what employees see in their inboxes and workflows, not abstract threats and generic policy reminders.

Start by establishing a baseline. You don’t need perfect data; you need enough signal to make smart decisions:

• What types of incidents keep showing up?
• Where do employees seem unsure (common helpdesk tickets, frequent questions)?
• Which workflows are most targeted (finance, HR, admin access, customer communications)?

Then segment your audience in a way that supports practical training. You don’t need elaborate personas. You need a few groups based on exposure and impact:

High-risk workflow teams

Finance, payroll, AP/AR, procurement - any team involved in payments, vendor changes, or approvals.

People-centric teams

HR, recruiting, executive assistants - roles that handle sensitive personal data and receive targeted impersonation attempts.

Privileged or technical users

Teams with elevated access or responsibilities that can impact broader systems.

Everyone else

The remainder of your workforce still needs foundational training focused on safe daily habits and reporting.

Once segmented, map the “pressure moments” attackers exploit - those moments where urgency, authority, or confusion leads to mistakes. This isn’t theoretical. These are the real situations your program should train for: “urgent payment change,” “account locked,” “shared file link,” “CEO request,” “callback to confirm,” and so on.

Day 15–21: Build your minimum viable program

This is where most teams overcomplicate the work. Don’t try to launch a perfect, all-inclusive program. Launch a minimum viable program that covers the most common human-risk behaviors and creates a repeatable cadence.

A strong launch month can be built around one idea: teach a habit employees can repeat under pressure.

Pause → Verify → Report

That single loop works across phishing emails, suspicious links, credential prompts, urgent requests, and impersonation attempts. It also gives you a consistent message to reinforce in training, internal communications, and follow-up coaching.

Within Cybrary SAT, your program foundation should align to the core awareness areas the SAT program emphasizes, including:

• Phishing awareness and email security
• Password hygiene and authentication practices
• Secure data handling and classification
• Remote work and mobile device security
• Incident reporting and response basics

As you structure the launch, keep the learner experience realistic. Employees shouldn’t leave training with a list of rules. They should leave with “I know what to do when I see something suspicious, and I’m confident reporting it.”

Day 22–30: Set reporting expectations and prepare your first phishing simulation

Security awareness succeeds in real moments, when an employee is deciding whether to click, whether to comply, or whether to report.

That means your program needs a strong reporting expectation. Every employee should know:

• What to report: anything suspicious or unexpected
• When to report: immediately
• Why it matters: early reporting prevents escalation
• What happens next: they will be supported, not blamed

Now plan your first phishing simulation as a baseline. Cybrary SAT includes a real-world phishing simulation experience powered by CanIPhish, designed to be realistic and measurable. Use your first simulation to establish where you are today and create a clear improvement target for the next 60 days.

Most importantly, decide your coaching approach before you run the simulation. If someone fails a simulation, they shouldn’t get shamed. They should get coached. Cybrary SAT supports this with integrated micro-learning for reinforcement after a miss, so the simulation becomes a learning moment, not a “gotcha.”

Day 31–45: Pilot, learn, and tune before scaling

Before you go organization-wide, run a pilot. This is how you move fast without creating confusion or negative sentiment.

Choose pilot groups that give you meaningful signals. A common approach is one high-risk group plus one broad group. Keep the pilot simple:

• Assign the initial SAT training
• Run the first phishing simulation
• Review the results: who clicked, who reported, who needs reinforcement
• Look for patterns by team and role

What you’re trying to learn during the pilot isn’t “Who made a mistake?” It’s:

• Do people recognize suspicious messages?
• Are they reporting quickly?
• Which themes cause the most confusion?
• What reinforcement will create the biggest behavior change?

The win here is a tuned program you can scale with confidence - one that’s grounded in your environment, not generic assumptions.

Day 46–60: Prepare your organization-wide rollout

Now you scale what worked and make the program feel consistent, manageable, and supportive.

Your rollout plan should include:

A clear cadence: Define how often employees will receive training and how often simulations will be run. Sustainable programs don’t overwhelm people; they reinforce learning over time.

A communications plan: Your internal messages should feel practical and non-threatening. Employees need to hear: what’s expected, why it matters, how to report, and that support is built in.

An engagement strategy: Participation improves when learning feels active and relevant. Cybrary SAT’s phishing simulation includes engagement elements like badges, streaks, and friendly competition to keep participation high without turning security into a punishment exercise.

A customization approach: Not every team faces the same risk. Cybrary SAT supports customizable modules and customizable campaigns so you can tailor training and simulations to match roles, risk levels, and organizational maturity.

Day 61–75: Launch organization-wide

Launch week is about clarity and consistency. Your launch message should make four things obvious:

Why this matters: Human error is a major risk driver, and training reduces breaches by helping employees stop threats before they escalate.

What employees need to do: Complete the assigned awareness training and report suspicious activity. If phishing simulations are part of your program, set expectations that they are used to practice skills safely.

What to expect going forward: Make the cadence clear so this doesn’t feel like a one-off assignment.

What the tone is: This program is coaching-first. Reporting is encouraged. Mistakes become learning opportunities.

Then run your first official phishing simulation window as part of the launch cycle. Use reporting and dashboards to identify who needs reinforcement and which teams require additional focus.

Day 76–90: Measure, improve, and lock in the cadence

The last 15 days are where awareness becomes a durable program instead of a one-time event.

Create a consistent monthly readout that includes:

• Training engagement (completion/participation trends)
• Simulation performance (click and report patterns)
• Who needs additional support
• The one or two improvements you’ll make next month based on what you learned

Then commit to continuous improvement. Your program doesn’t need to change everything every month. It needs to improve one thing every month.

Examples:

• If reporting is low, reinforce reporting expectations and reduce friction in how employees escalate.
• If simulation outcomes are poor, adjust campaign difficulty and increase reinforcement for the most common failure pattern.
• If one team lags, tailor campaigns and training to match that team’s workflow risks.

By day 90, you should have a steady cadence that includes ongoing training, phishing simulation practice, and a repeatable measurement rhythm that proves improvement over time.

Common pitfalls to avoid

If you want to launch fast and build trust, avoid these mistakes:

• Waiting for perfection before launching
• Treating simulations as “gotchas” instead of coaching moments
• Measuring completion without measuring behavior change
• Overloading employees with long training blocks
• Keeping the program generic instead of practical and role-aware

If you want to launch a measurable security awareness program in 90 days, using practical training, real-world phishing simulation, and built-in reporting, explore Cybrary’s Security Awareness Training is the answer.