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

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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

Services

What 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.

Odyssey Network Assessment

$100

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

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Odyssey Autonomous Pen Test

One time or Subscription (PTaas)

Quick setup and no impact on ops
Finds and connects hidden weaknesses like a real attacker
Proves exactly how your business could be harmed
Prioritized fix guidance in plain language
One-time or scheduled, recurring security tests
Covers cloud and on-premise systems
Internal and external testing

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Odyssey Compliance Assessment

$100

Snapshot of your GRC posture
Gap analysis against industry best practices/benchmarks
Stakeholder interviews and workshops
Review of existing policies and controls
Identification of critical risks and vulnerabilities
Prioritized improvement roadmap
Framework selection guidance
One-time engagement with optional support services

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Odyssey Penetration Test

Determined after needs are identified

Network assessment included
Real-World Threat Simulation
Dynamic Threat Monitoring
Customized Attack Scenarios
Detailed Testing Reports & Artifacts
Advanced Remediation Guidance

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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

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Gives you a holistic baseline view of your entire IT and technology infrastructure from security and risk to planning and roadmapping.

A full report and engineer led review of the findings that includes actionable items and advice that can be implemented by your team or any provider.

Organizations with no dedicated IT team or a small one that wants to make sure their infrastructure is not a security risk or roadblock to their growth.

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

Find – Fix - Verify

Odyssey's Autonomous Penetration Test simulates real-world attacks across your entire infrastructure to show you not just where you're vulnerable, but exactly how you could be compromised. One-time or recurring, you get a full report and hands-on engineer review with prioritized remediation steps at a measurable cost savings.

How It Works:

Autonomous Risk Assessment — Runs intelligent, self-directed testing across your environment to identify real, exploitable security gaps

Simulated Real-World Attacks— Replicates modern attacker behavior to show exactly how your systems could be breached

Verified Exploitation & Reporting— Delivers validated findings with actionable, prioritized steps to reduce risk fast

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Gives you a full infrastructural picture of not just checklist potential vulnerabilities but actual attacker validated risks.

A full report and engineer led review of all uncovered weaknesses and attacks and remediation steps that can be taken to solve them.

Organizations who are required to conduct regular pen testing or looking to confirm the protections they have in place are working.

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

A Business Leader's Guide to Enterprise AI Adoption in 2025

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Learn some unique ways to save money and get some big deductions come tax season from Usherwood CFO Andrew Flamik.

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Properly Managing Your IT Equipment 101

If you’re not an IT expert, it can be difficult for businesses to know the ins and outs of IT equipment. This can include proper maintenance.

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What to Expect

Full Attack Visibility

We safely simulate real-world cyberattacks across your environment to uncover how vulnerabilities can actually be exploited.

Clear, Prioritized Plan

A detailed, step-by-step guide to address security gaps, with prioritized recommendations to reduce risk quickly.

Expert Review & Guidance

We review findings together to ensure your team understands the risks and how to effectively remediate them.

At the end of your assessment, you’ll receive a comprehensive report with verified findings and clear next steps—whether you address them internally or partner with Usherwood to strengthen your security posture.

A smarter way to stay ahead of risk

Odyssey's Compliance Assessment cuts through the complexity of GRC by giving you a clear baseline of where your organization stands against your target framework and what gaps need to be closed. From policy review to prioritized roadmap, you walk away with expert-led guidance and actionable next steps — not just findings.

Custom Compliance Assessment: We evaluate your organization against your chosen framework to establish a clear baseline of your current GRC posture

Stakeholder Collaboration: Through interviews and workshops, we align business, IT, and leadership priorities to ensure accurate, real-world insight.

Gap Analysis & Roadmap: We identify compliance gaps and deliver a prioritized, actionable path toward meeting framework requirements.

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Provides a baseline understanding of gaps in your organization that need to be addressed in order to become compliant for a particular framework.

A GRC expert led review of findings and what actions are needed to become compliant for a specific framework.

Any organization that needs to adhere to a compliance framework currently or operates in an industry that has compliance requirements

What to Expect

Clear Compliance Baseline

We provide a comprehensive snapshot of your current posture, highlighting where you meet requirements and where gaps exist.

Prioritized Action Plan

A structured roadmap with clear, actionable steps to help you close gaps and move toward compliance with confidence.

Guided Expert Support

We walk through findings with your team, ensuring you understand requirements, risks, and the best path forward.

At the end of your assessment, you’ll receive a detailed report with clear next steps—whether you implement them internally or work with Usherwood to advance your compliance journey.

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

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Provides a penetration test that can be custom tailored to your organization’s infrastructure and it’s unique needs and dive deep into a specific facet of your environment.

After completion of the test you’ll receive a full risk assessment with actionable next steps.

Organizations with a mature IT environment who are looking to make sure it stays that way in an ever evolving threat landscape.

Penetration Testing 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

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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

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.

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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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