IT Assessments & Penetration Testing
Why Invest in an IT Assessment or Penetration Test?
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
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
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
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
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
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.
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
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Properly Managing Your IT Equipment 101
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What to Expect
Full Attack Visibility
Clear, Prioritized Plan
Expert Review & Guidance
FAQs
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.
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.
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.
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.
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.
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.
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
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.
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.
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.
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.
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.
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.
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
Clear Compliance Baseline
Prioritized Action Plan
Guided Expert Support
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.
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
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
IT Infrastructure Assessment
Evaluating networks, systems, and security controls to identify vulnerabilities and configuration weaknesses
Wireless Network & Segmentation Testing
Testing wireless security and network boundaries to uncover unauthorized access and lateral movement risks
Web Applications & API Testing
Identifying vulnerabilities in web applications and APIs that could expose sensitive data or critical systems
OSINT & Reconnaissance
Mapping your external attack surface through open-source intelligence and adversary-style reconnaissance
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.

