IT Assessments & Penetration Testing

Proactively Protect Your Business from Cyber Threats

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Why Invest in an IT Assessment or Penetration Test?

Cyberattacks have surged by 500% since 2020—making it a matter of when, not if, your business will be targeted. For small and medium-sized businesses (SMBs), the stakes are even higher:

43% of cyberattacks now target SMBs

60% of SMBs that suffer an attack go out of business within six months

The average cost of a breach for SMBs is $2.2 million

Comprehensive IT assessments and network penetration testing are critical investments, providing the insights you need to identify vulnerabilities, prioritize risks, and take action before attackers do.

The Usherwood Difference

Beyond Free & Low-Cost Assessments

Not all IT assessments and penetration tests are created equal. Many "free" or low-cost alternatives rely on automated scans that provide surface-level results, missing critical gaps in security.

These limited assessments:

Depend on generic scanning tools with minimal depth

Fail to provide meaningful analysis or action plans

Leave you with more questions than answers

Why Choose Usherwood's Odyssey Approach?

Usherwood’s Odyssey IT Assessments & Penetration Tests go beyond automation. Our expert engineers and security specialists analyze your IT environment in real-world conditions to provide actionable insights—not just generic reports.

Comprehensive, Human-Led Analysis

Our security experts dig deeper than automated tools ever could

Actionable Roadmaps

We prioritize risks and provide a clear strategy to mitigate them

360 Visibility

From cybersecurity posture to compliance and long-term IT planning, we cover it all

Real-World Testing

Simulating actual cyber threats, not just theoretical risks

Odyssey Discovery Network Assessment

$100 per full network user

Cybersecurity Posture
Vulnerability Assessment
Compliance Review
Patching State Analysis
IT Infrastructure Review
Endpoints & Active Directory Review
Licensing Audit
360 IT Infrastructure Review
3-Year IT Roadmap & Budget Planning
Risk Prioritizing & Remediation Plan

Odyssey Penetration Test

Determined after needs are identified

Cybersecurity Posture
Vulnerability Assessment
Compliance Review
Patching State Analysis
IT Infrastructure Review
Endpoints & Active Directory Review
Licensing Audit
360 IT Infrastructure Review
3-Year IT Roadmap & Budget Planning
Risk Prioritizing & Remediation Plan
Real-World Threat Simulation
Dynamic Threat Monitoring
Customized Attack Scenarios
Detailed Testing Reports & Artifacts
Advanced Remediation Guidance

Which is Right for My Organization?

Not sure what option is best for you? If you are early in your IT improvement journey, a network assessment might be the best option. However, if you have made investments in your security and you're looking to verify effectiveness, a penetration test might be best. Each business is unique though, and a short intro call with our team to answer a few questions will help determine the best choice for you.

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Odyssey Discovery Network Assessment

A 360° IT Health Check

Our Odyssey Discovery Network Assessment goes beyond a typical security scan from a penetration testing company - it’s an in-depth evaluation of your entire IT environment.

Your dedicated team of specialists includes:

Project Engineer & Senior Project Engineer
Virtual Chief Information Officer (vCIO)
Strategic Technology Consultant
Sales Engineer

What to Expect

Full Network Evaluation

We analyze every device and application to find vulnerabilities in your environment

Clear Action Plan

A prioritized, step-by-step guide to address security gaps

Collaboration with Your Team

We ensure findings are understood and actionable

At the end of this assessment, you’ll receive a detailed report with clear next steps—whether you implement them in-house or work with Usherwood to strengthen your security.

See a Sample Report

Simulating Real-World Cyberattacks

Odyssey Penetration Testing

Unlike automated penetration tests that generate cookie-cutter reports, our Odyssey Penetration Test mimics real-world attacks to uncover hidden vulnerabilities and simulate actual threats to your business.

How It Works:

Custom Risk Assessment —We tailor the test to your business needs, ensuring realistic attack scenarios

Simulated Cyberattacks—Testing against the latest hacker tactics to expose weaknesses before attackers do

Detailed Reporting & Remediation—Prioritized insights to fix vulnerabilities and improve security posture

Penetration Testing Services We Offer:

OSINT & Reconnaissance
IT Infrastructure Assessment
External & Internal Penetration Testing
Wireless Network & Segmentation Testing
Social Engineering & Physical Security Assessments
Web Applications & API Testing
Assumed Breach

At the end of the penetration test, you’ll receive a full risk assessment with actionable next steps, ensuring your business is prepared for modern threats.

Advanced Types of Penetration Testing Services

For organizations already conducting regular security testing, we offer advanced Red Team and Assumed Breach exercises to simulate sophisticated attack scenarios.

Purple Team Testing

Red vs. Blue team engagement to improve your IT team's threat response

Assumed Breach Testing

Simulating attacks from compromise credentials to identify lateral movement risks

Payload & Delivery Testing

Testing how malware bypasses security tools

Red Team Penetration Testing

Full-scale, stealth-based ethical hacking to test your defenses against real-world threat actors

Learning Center

Your IT Questions, Answered

The Learning Center provides digital knowledge from our subject matter experts, so you have everything you need to make informed IT decisions

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Take Control of Your IT Security Today

Cyber threats won’t wait—neither should you. Invest in a comprehensive, expert-led IT assessment or penetration test with Usherwood and gain the confidence to protect your business.

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Ready to get your technology to work for you?

IT Assessments & Penetration Testing