Penetration Testing Services for Enterprise Companies

Protect your enterprise against evolving threats with manual, multi-vector penetration testing designed to expose vulnerabilities before attackers exploit them. DeepSeas conducts rigorous adversary simulations across network infrastructure, cloud environments, and web applications using real attacker tradecraft. Gain actionable remediation guidance, meet stringent regulatory standards, and validate your defensive posture with proven testing backed by thirty years of cyber defense experience.

Cybersecurity specialist analyzing penetration testing attack simulation data

Our Penetration Testing Services

Comprehensive offensive security assessments delivering real-world attack simulations to uncover hidden vulnerabilities across your systems.

Network Penetration Testing

Manual assessments across external and internal networks, Active Directory, and wireless systems using real attacker tradecraft to uncover hidden attack chains that automated scanners miss, complete with prioritized remediation guidance.

Cloud Penetration Testing

Rigorous adversary simulations evaluating IaaS, PaaS, and SaaS environments to identify misconfigurations, excessive permissions, and exposed secrets, backed by manual validation and free remediation retesting within six months.

Web Application Testing

Hands-on evaluation of web apps, mobile apps, and APIs focused on complex business logic flaws, access control gaps, and authentication weaknesses that automated vulnerability scanners cannot identify.

Red Team Emulation

Objective-driven adversary simulations testing organizational detection, response, and containment capabilities against real-world threat actor techniques operating stealthily across digital and physical perimeters over extended timelines.

Social Engineering Testing

Realistic email phishing, vishing, smishing, and physical access evaluations designed to measure workforce response capabilities, reporting speed, and technical control enforcement without penalizing individual employees.

Compromise Assessment

Specialized threat hunting across endpoints, identities, and network telemetry to determine whether unauthorized actors have established persistence or compromised critical systems within your environment.

Real Attacker Tradecraft

Adversary-Grade Security Testing That Proves Your Defensive Resilience

Automated vulnerability scans only uncover known signatures and leave complex attack vectors hidden. DeepSeas conducts thorough manual penetration testing that mimics genuine adversary tactics across your applications, cloud infrastructure, and internal networks. Our ethical hackers identify chained exploit paths, eliminate false positives, and deliver actionable remediation roadmaps that satisfy strict regulatory frameworks and equip your security leadership with verifiable defense metrics.

Penetration tester analyzing system vulnerabilities on dual monitors
Trusted by Industry Leaders

Proven Security Outcomes

See how organizations validate their security posture and eliminate critical risks through targeted offensive testing.

"In cybersecurity we were not looking for a vendor, we were looking for a trusted partner that could push us, challenge us, and ensure we got better at protecting our systems every day. We found that partner with DeepSeas, and they have helped us be far smarter and better than..."

JIM IBISTER
JIM IBISTER
The DeepSeas Difference

Why Choose DeepSeas?

Decades of cyber defense expertise protecting enterprises against sophisticated threat actors.

Decades of Experience

Delivering complete cyber defense backed by thirty years of operational security expertise across critical enterprise environments.

Manual Tradecraft

Certified ethical hackers uncover nuanced attack paths and business logic vulnerabilities that automated vulnerability scans miss.

Certified Specialists

Engagements conducted by specialists holding industry-leading offensive certifications including OSCP, OSCE, and OSWP designations.

Free Retesting

Validate your remediation efforts with complimentary retesting within six months to confirm identified vulnerabilities are resolved.

Meet The DeepSeas Team

Seasoned cybersecurity leaders dedicated to safeguarding enterprise operations.

Portrait of Lewie Dunsworth, Chief Executive Officer at DeepSeas

Lewie Dunsworth

Chief Executive Officer

Lewie Dunsworth serves as Chief Executive Officer of DeepSeas, leading the company's mission to make cybersecurity a strategic advantage for nearly 1,000 organizations worldwide. Under his leadership, DeepSeas has grown into a recognized leader in Managed Detection and Response, earning recognition from Gartner and Frost & Sullivan as a top provider in the industry. Lewie drives the company's vision across its six-layer cyber defense stack, spanning strategic advisory, offensive security, threat intelligence, managed detection and response, the CyberFusion SOC, and governance, risk and compliance. He is committed to ensuring that enterprise, mid-market, government, and education clients receive proactive, measurable, and customized cybersecurity outcomes. Lewie's leadership reflects nearly three decades of industry experience and a steadfast focus on client trust and operational excellence.

Portrait of Keith Robertson, Risk Management and Compliance Executive at DeepSeas

Keith Robertson

CISM, CIPP/E, SANS GCIH, GIAC, HITRUST

Keith Robertson brings 25 years of governance, risk management, and compliance experience to DeepSeas, including prior service as a Fortune 500 Chief Security Officer and Enterprise Risk Officer. He holds an impressive array of certifications, including CISM, CIPP/E, SANS GCIH, GIAC, and HITRUST, reflecting his comprehensive expertise across security management, privacy, incident handling, and healthcare compliance. Keith's executive-level experience gives him a unique perspective on enterprise risk, allowing him to help DeepSeas clients align cybersecurity strategy with broader business objectives. His background in high-stakes corporate security leadership positions him well to guide organizations through complex governance challenges and regulatory requirements. Keith is committed to helping clients build mature, enterprise-grade risk management programs that support long-term security and compliance success across diverse industries.

Portrait of Sean Duffy, Cybersecurity and Legal Advisor at DeepSeas

Sean Duffy

CISSP, CCSK, Licensed Attorney

Sean Duffy combines 25 years of cybersecurity experience with a unique legal background, holding both CISSP and CCSK certifications as well as a license to practice law. A United States Navy veteran, Sean brings a disciplined, mission-focused approach to his work advising C-suite executives and boards of directors on cybersecurity strategy and risk. His legal expertise allows him to provide clients with a nuanced understanding of regulatory and liability considerations alongside technical security guidance, a combination that is especially valuable for organizations navigating complex compliance landscapes. Sean's extensive advisory experience makes him a trusted voice for senior leadership teams seeking to understand cybersecurity risk in business terms. His military background and legal training reflect the depth and diversity of expertise that defines the DeepSeas team.

Portrait of Matt Lammers, CISO and IT Risk Executive at DeepSeas

Matt Lammers

CISSP, HITRUST

Matt Lammers is an experienced CISO and IT risk executive who brings both deep technical certification and management consulting experience to DeepSeas. Holding CISSP and HITRUST credentials, Matt has built a career helping organizations strengthen their cybersecurity posture while managing enterprise-level risk. His consulting background equips him with strong skills in translating complex security concepts into actionable business strategies for executive stakeholders. Matt's international perspective, including his status as an Australia permanent resident, gives him valuable insight into global compliance and security considerations that benefit DeepSeas clients operating across borders. He is dedicated to helping organizations build resilient, well-governed cybersecurity programs that align with both operational needs and executive priorities, reinforcing DeepSeas' commitment to customized, outcome-driven security solutions.

Frequently Asked Questions

How much should a penetration test cost?

Penetration testing costs vary depending on the scope, environment complexity, and testing methodology required. Factors influencing pricing include the number of target IP addresses, application user roles, cloud architectures, and whether physical or social engineering vectors are included. DeepSeas scopes each engagement individually based on your specific infrastructure and compliance objectives, providing transparent quotes within twenty-four hours upon request to ensure predictable budgeting.

What is the difference between vulnerability scanning and penetration testing?

What methodologies and certifications do your penetration testers hold?

How often should our company perform a penetration test?

Do penetration tests cause disruptions to business operations?

What deliverables are included with a DeepSeas penetration test?

Can penetration testing help satisfy compliance frameworks like SOC 2 and ISO 27001?

Does DeepSeas offer retesting after vulnerabilities are remediated?

Have Additional Questions About Penetration Testing?

Speak with our offensive security team to scope your testing requirements.

Certified & Recognized

Awards and Recognition

Gartner top 40 recognition logo

Gartner Top 40 MDR Provider

Recognized as a top provider in Managed Detection and Response.

Frost Radar MDR Leader logo

Frost Radar MDR Market Leader

Named a leader and top-five global MDR provider.

Frost and Sullivan Leadership Award logo

Frost & Sullivan Leadership Award

Honored with the competitive strategy leadership award in MDR.

Global MDR Best Practices logo

Global MDR Best Practices Award

Recognized for strategic excellence in global MDR service delivery.

Protect Your Organization with Expert Penetration Testing

Reach out to our offensive security team to discuss your scope, objectives, and testing timelines.

Request Penetration Testing Services

To help us assist you faster, please include the reason for your message so the relevant team can reach out as soon as possible.