Cybersecurity Self-Assessments and Questionnaires

Turn security questionnaires and self-assessments into clear, defensible evidence. DeepSeas helps organizations identify control gaps, document risk, organize audit-ready information, and respond confidently to customers, insurers, regulators, and procurement teams. With practitioner-led cybersecurity, governance, risk, and compliance expertise, your organization can replace scattered answers with a structured view of security posture and practical next steps.

Cybersecurity team reviewing security questionnaire and assessment findings

Our Cybersecurity Self-Assessment Services

Assessment, compliance, testing, and advisory services help organizations answer security questions with evidence and confidence.

Cybersecurity Risk Assessment

Evaluate information security strengths, weaknesses, and prioritized risks through stakeholder interviews, asset inventory, risk workshops, scenario analysis, and documented treatment planning.

Security Risk Assessments

Use controlled penetration tests and attack simulations to identify weaknesses across applications, infrastructure, and processes before real attackers exploit them.

Compliance Readiness

Prepare for customer, regulatory, insurance, or certification requirements with gap assessments, documentation development, evidence organization, and audit preparation support.

Governance Risk Compliance

Build and operate governance programs with control development, policy support, continuous controls monitoring, risk scoring, evidence packaging, and board-ready reporting.

Strategic Security Advisory

Get senior guidance for security strategy, board discussions, customer reviews, insurance requirements, acquisitions, and decisions about capabilities and priorities.

Security Program Development

Create a practical security program through baseline assessment, roadmap development, foundational policies, operational integration, and continuous improvement.

Evidence-Based Assurance

Answer Security Questions With Confidence

DeepSeas helps you move beyond checkbox responses by connecting questionnaire answers to documented controls, risk decisions, operational evidence, and prioritized remediation. Whether a customer review, insurer request, regulatory requirement, or internal assessment is driving the work, practitioners can clarify what is in place, identify what needs attention, and organize responses that are accurate, defensible, and useful for improving the underlying security program.

Security advisor organizing evidence for a cybersecurity questionnaire
Built For Confidence

Security Outcomes

Practical assessment support helps leaders, customers, insurers, and auditors understand your security posture.

"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?

DeepSeas combines assessment discipline with practical cybersecurity expertise and measurable outcomes.

Practitioner-Led

Hands-on specialists connect questionnaire responses to real controls, operations, risk, and remediation priorities.

Broad Expertise

Security, governance, compliance, offensive testing, advisory, and detection capabilities support connected answers.

Defensible Evidence

Organized findings and documentation help stakeholders evaluate security posture without relying on unsupported claims.

Nearly 30 Years

DeepSeas brings approximately 30 years of cyber defense experience serving organizations worldwide.

Meet The DeepSeas Team

Experienced cybersecurity practitioners help turn complex requirements into actionable security outcomes.

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

What is a cybersecurity self-assessment?

A cybersecurity self-assessment is a structured review of an organization’s security controls, processes, technology, governance, and risk. It may be completed for internal planning, a customer security questionnaire, an insurer, a regulator, or a compliance requirement. A useful assessment identifies what is in place, what evidence supports it, where gaps exist, and which actions should be prioritized.

How can DeepSeas help answer security questionnaires?

What information is needed for a cybersecurity self-assessment?

Can a self-assessment identify cybersecurity gaps?

Can DeepSeas support customer security reviews?

Does a questionnaire response replace a cybersecurity assessment?

Can DeepSeas help with compliance and audit preparation?

What happens after a cybersecurity self-assessment?

Need Help With Your Assessment?

Talk with DeepSeas experts about your questionnaire, evidence, and security priorities.

Recognized Expertise

Awards and Recognition

ISO Lead Auditor certification recognition

ISO Lead Auditor certifications

ISO Lead Auditor certifications held by DeepSeas specialists.

Gartner top 40 Managed Detection and Response recognition

Gartner top 40 Managed Detection and Response provider recognition

Recognition as a top 40 Managed Detection and Response provider by Gartner.

2024 Frost Radar Managed Detection and Response recognition

2024 Frost Radar Global Managed Detection and Response Market Leader and top-five provider recognition

Recognition as a Leader and top-five provider in the 2024 Frost Radar market.

Frost and Sullivan 2024 Competitive Strategy Leadership Award

Frost & Sullivan 2024 Best Practices Competitive Strategy Leadership Award for Managed Detection and Response

Award recognizing Competitive Strategy Leadership in Managed Detection and Response.

2024 Global MDR Best Practices Award for Strategy

2024 Global MDR Best Practices Award for Strategy

Recognition as the recipient of the 2024 Global MDR Best Practices Award for Strategy.

Strengthen Your Security Assessment Response

Share your questionnaire, assessment objective, or evidence challenge and discuss practical next steps with DeepSeas.

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