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IT Assessments & Penetration Testing

Proactively protect your business from cyber threats 

 

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: 
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:

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.
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 per user

  • 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

Odyssey Autonomous Pen Test

One time pen test

$2,500 - $15 per IP over 100 IP’s

Pen Testing Service

$125 per mo. - $1.25 mo. per IP over 100

Quarterly reporting

  • 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

Odyssey Compliance Assessment

 Determined after framework identified 

  • 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

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
Our Offerings

Odyssey 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

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

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.
Our Offerings

Odyssey Autonomous Pen Testing

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:

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

What to Expect

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.

FAQs

Why does Usherwood's autonomous pen test cost less than a manual pen test?

A manual pen test relies on a team of consultants spending days or weeks manually probing your network by hand, which is expensive labor. Our autonomous pen test uses machine learning to do that same attack work in a fraction of the time. That lower overhead lets us pass the savings on to you, while testing more of your network than a manual test would cover and still delivering a human expert interpretation of findings.

What's the difference between a pen test and a vulnerability scan?

A vulnerability scan just checks your systems against a list of known issues and tells you what might be a problem. It does not try to break in. A pen test goes a step further and actually attempts to exploit those weaknesses, the same way a real attacker would, to prove whether they can truly be used to access your data or systems. Think of a scan as spotting an unlocked door, while a pen test actually walks through it to see what's on the other side.

Can Usherwood's autonomous pen test satisfy companies who are required to run a pen test annually?

Yes. Organizations use it to meet annual pen test requirements tied to standards like SOC 2, HIPAA, and PCI-DSS. Because it can be run more than once a year if needed, it also gives you a stronger story for auditors, showing ongoing testing rather than a single point in time snapshot.

Is Usherwood's autonomous pen test internal and external?

Yes. It covers both. Internal testing looks at what could happen if someone already has a foothold inside your network, such as a compromised employee account. External testing looks at your organization from the outside, the same way an attacker on the internet would, to find exposed systems and weak entry points at your perimeter.

What is this and how is it different from a regular pentest?

It's an automated penetration test that actually attacks your network the way a real hacker would, instead of just scanning for known issues. Most security scans just list possible problems. This tool proves which ones are actually exploitable, so you know what is truly putting you at risk.

How long does a test take to set up and run?

You can launch a test in minutes. There's no lengthy setup and no agents needed on every device. For internal tests, we spin up a small virtual or onsite machine or container. External tests run entirely from the cloud. Testing is completed in one day and can be run while continuing daily operations.

What kind of weaknesses does it find?

It looks well beyond the basic vulnerability list. It checks for weak or reused passwords, misconfigured systems, exposed cloud storage, and gaps in identity and access controls. It then chains these weaknesses together to show what an attacker could actually achieve, not just a list of separate issues

Will this cause any downtime or break anything?

It's built to be safe by default. It tests live systems without disrupting normal operations, and it doesn't require risky changes to your network to run.

What do we get when the test is done?

A clear report showing exactly what was found, proof that it was exploitable, and step by step guidance on how to fix it. Reports are written for both technical teams and leadership, so everyone understands the real business risk and are delivered by our security specialists to answer any questions.

Can it test our cloud environment too?

Yes. It can assess cloud platforms like AWS and Azure along with on premises networks, and it can show how a weakness in one area, like a cloud misconfiguration, could be used to break into another part of your environment.

Once we fix something, how do we know it actually worked?

You can re-run a focused test to confirm the fix closed the gap. This gives you proof the issue is resolved instead of just hoping it is.

Does this help with compliance requirements?

Yes. Many organizations use it to meet penetration testing requirements tied to frameworks like SOC 2, HIPAA, and PCI-DSS, and to show auditors that security testing is happening on an ongoing basis rather than once a year.

What is the difference between the one time and monthly subscription model?

The same test is run in both situations but a monthly subscription model runs the test quarterly to stay ahead of ever-changing threats. This model can help your IT team to take care of uncovered issues as they arise in smaller, easier to manage pieces instead of waiting a whole year and letting remediation projects pile up.

Our Offerings

Odyssey Compliance Assessment

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. 

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

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.
Our Offerings

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:

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.

 

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.
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.
Get Started

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.