Cybersecurity Executive

Expert Witness

30+ years in Digital Forensic & Incident Response Investigations

Virtual CISO

Independent reviewer for cyber related Reps & Warranties Claims

Extensive experience collaborating with law firms, insurance carriers, threat actor communications, managed service providers, IT remediation & eDiscovery services.

Andrew P. Obuchowski, Jr.

Professional Experience

Cybersecurity & Incident Response Services Advisor

Boston MA

2022 — Present

Provide consulting services for technology services firms on business operations, managed services processes and automation, digital forensic best practices, incident response investigations & remediation plans, expert report writing and testimony, and client experiences.

Advise technology services organizations on business operations, service delivery optimization, and managed services transformation initiatives, helping clients improve operational efficiency, scalability, profitability, and customer satisfaction.

Provide consulting on managed services processes, workflow automation, and service management best practices to enhance operational performance and strengthen organizational maturity.

Counsel clients on digital forensics, cyber incident response, and investigative best practices, including evidence preservation, forensic readiness, incident management, remediation planning, and post-incident recovery strategies.

Develop and refine incident response frameworks, playbooks, and remediation programs designed to improve cyber resilience, reduce operational risk, and support regulatory and contractual obligations.

Provide expert guidance on forensic reporting, technical documentation, and expert witness preparation, ensuring investigative findings are communicated clearly and defensibly for legal, regulatory, and business stakeholders.

Serve as a trusted advisor on cybersecurity, digital investigations, managed services operations, and organizational transformation, helping clients align technology, risk management, and business objectives.

Vice President, Forensic Services

Charles River Associates, Boston MA

2016 — 2022

Practice Co-Chair for Digital Forensics and Incident Response (DFIR) services, leading the delivery of cybersecurity consulting engagements across diverse industry sectors with a focus on small and middle-market enterprises.

Provide strategic leadership and technical oversight for cyber incident response engagements, including ransomware events, data breaches, business email compromise investigations, insider threat matters, and other complex cybersecurity incidents.

Lead and mentor multidisciplinary teams responsible for threat containment, eradication, recovery, and forensic investigations, leveraging Endpoint Detection and Response (EDR) technologies and industry-leading investigative methodologies to identify, analyze, and mitigate cyber threats.

Advise executive leadership, legal counsel, insurers, and other stakeholders throughout the incident lifecycle, providing risk-based recommendations and actionable guidance to support business continuity and regulatory compliance.

Direct threat actor engagement and negotiation support activities, coordinating response strategies and communications while assessing operational, legal, and reputational risks associated with cyber incidents.

Drive the development and enhancement of incident response capabilities, forensic methodologies, and service offerings to improve operational effectiveness, client outcomes, and cybersecurity resilience.

Practice Leader - Digital Forensics & Incident Response Services

RSM, Boston MA

2013 — 2016

Lead all cybercrime, digital forensics, and data breach investigations across the United States, while providing technical expertise and strategic advisory support for complex cross-border and international matters involving cyber incidents, electronic evidence, and regulatory inquiries.

Direct the delivery and expansion of cybersecurity, privacy, and risk advisory services, including PCI DSS compliance assessments, HIPAA and IT risk assessments, network vulnerability testing, incident response preparedness, tabletop exercises, red team engagements, and cyber resilience programs.

Advise clients on the identification, assessment, and mitigation of cybersecurity risks through the development of tailored security strategies, incident response plans, and governance frameworks aligned with industry standards and regulatory requirements.

Oversee multidisciplinary teams responsible for conducting security assessments, penetration testing exercises, cyber investigations, and forensic examinations, ensuring high-quality service delivery, technical excellence, and client satisfaction.

Support legal, regulatory, and corporate stakeholders by providing expert analysis, investigative findings, and risk-based recommendations related to cyber incidents, privacy matters, and complex dispute engagements.

Lead early case assessments and investigative planning efforts to evaluate technical, legal, and business risks, establish engagement strategies, and support informed decision-making throughout the matter lifecycle.

Associate Director - Disputes & Investigations

Navigant (Currently Ankura), New York NY

Design, implement, and continuously improve standardized investigative methodologies and operational procedures for data breach response, complex digital forensic investigations, network vulnerability assessments, and cybersecurity risk evaluations, ensuring consistency, efficiency, and defensibility across engagements.

Serve as a subject matter expert in information security, digital forensics, cyber incident response, digital investigations, and electronic discovery, providing strategic guidance to clients, legal counsel, and internal stakeholders on complex technical and regulatory matters.

Drive business development initiatives by identifying client needs, developing service offerings, supporting proposal and engagement activities, and cultivating trusted advisor relationships within the cybersecurity, digital forensics, and eDiscovery markets.

Lead and manage client engagements involving complex litigation, regulatory investigations, cybersecurity incidents, internal investigations, and other high-stakes dispute matters, ensuring timely delivery, technical excellence, and client satisfaction.

Collaborate with multidisciplinary teams, including legal, compliance, risk, and technology professionals, to develop investigative strategies, communicate findings, and support informed decision-making throughout the engagement lifecycle.

2011 — 2013

Managing Consultant - Digital Forensics & Incident Response Services

Kroll, New York NY

2013 — 2016

Lead and manage teams responsible for data breach investigations, complex digital forensic examinations, network vulnerability assessments, and rapid security response engagements by establishing structured processes, standardized workflows, and documentation practices that support efficient, repeatable, and defensible investigative operations.

Develop and enhance electronic discovery, digital forensics, and incident response procedures to improve operational effectiveness, maintain evidence integrity, and align investigative practices with industry standards and best practices.

Prepare comprehensive technical and expert reports documenting investigative methodologies, forensic findings, security assessments, remediation recommendations, and data breach analysis for legal, regulatory, and business stakeholders.

Collaborate with internal teams, external partners, and clients to communicate technical findings, assess risk, and provide strategic guidance related to cybersecurity incidents, digital evidence, and investigative outcomes.

Senior Information Protection Specialist

CIGNA Healthcare, Bloomfield CT

Conducted digital forensics and e-discovery services supporting litigation, regulatory matters, internal investigations, and incident response activities.

Developed, evaluated, and implemented policies, procedures, and workflows for the preservation, collection, processing, analysis, storage, and management of digital evidence in alignment with industry standards and accepted forensic practices.

Provided technical leadership, mentorship, and training to team members on digital forensic methodologies, emerging technologies, investigative techniques, and best practices for handling electronic evidence.

Advised investigative teams and stakeholders on matters involving digital evidence, cyber-related incidents, and technology-based misconduct or compliance concerns.

Performed remote and on-site forensic engagements, including data acquisition, evidence preservation, encryption/decryption activities, secure data transfer, and coordination with external forensic service providers and vendors.

Maintained chain-of-custody documentation and ensured the integrity, confidentiality, and defensibility of digital evidence throughout the investigative lifecycle.

2007 — 2009

Academy Instructor

Massachusetts Police Training Committee, Greater Boston, MA

2002 — 2009

Served as a classroom instructor for basic and advanced computer crime investigations, delivering structured training on identity theft, digital evidence identification and seizure, applicable state and federal statutes, relevant case law, and foundational and advanced technology concepts.

Designed and delivered instructional content covering digital forensic principles, investigative methodologies, and legal frameworks governing cybercrime investigations and electronic evidence handling.

Educated law enforcement personnel and investigative professionals on emerging technology trends, terminology, and their practical application within criminal investigations and digital forensic examinations.

Translated complex technical and legal concepts into accessible instruction to support operational readiness, investigative effectiveness, and adherence to evidentiary standards.

Computer Forensic Analyst - Supervisor

Regional Electronic & Computer Crimes Task Force, Greater Boston, MA

2002 — 2009

Led and coordinated complex digital investigations involving cybercrime, electronic evidence, and technology-related offenses across multiple jurisdictions, collaborating with local, state, and federal law enforcement agencies to support criminal matters.

Conducted and oversaw the forensic acquisition, preservation, examination, and analysis of computers, mobile devices, video systems, and other digital evidence while ensuring compliance with established forensic methodologies, evidentiary standards, and chain-of-custody requirements.

Prepared comprehensive investigative reports and forensic findings for criminal prosecutions and legal proceedings, translating complex technical evidence into clear conclusions for district attorneys, judges, and other stakeholders.

Provided expert witness testimony in state and federal court proceedings regarding digital forensic methodologies, investigative findings, electronic evidence handling, and cybercrime-related matters.

Developed and delivered specialized training programs and educational presentations for law enforcement personnel, legal professionals, and technology practitioners on digital investigations, cybercrime trends, information technology, and the intersection of technology and criminal law.

Authored detailed legal and investigative documentation, including affidavits, search warrants, subpoenas, administrative orders, and supporting case materials to facilitate lawful evidence collection and investigative activities.

Served as a Sworn Special Deputy with the United States Marshals Service, supporting multi-jurisdictional investigations and enforcement actions involving digital evidence and technology-related crimes.

Expert Witness

Provide expert reports, affidavits, and testimony tailored for court proceedings. Support legal teams throughout litigation including strategy and examination/cross-examination of witnesses.

Leadership

Expertise

Core Skills & Strategic Competencies

Expertise building and leading global cybersecurity teams and services, business operations, and methodologies.

Digital Forensics

Extensive expertise in investigations and incident response for cyber related attacks, insider threats, and intellectual property theft.

Professional Development

Career coach for cybersecurity team members including training, though leadership, written/verbal communications, and investigation methods.

Cyber Resilience

Organizational expertise for SME's in identifying risks and developing strategies to minimize future disruption to business operations.

Client Relations

Develop reliable technical frameworks and workflows that provide law firms with clear, practical results through a committed professional partnership.

Academic Foundation

2018 — 2020

MS, National Security

London School of Economics and Political Science. Focus on disruptive leadership and organizational transformation through contemporary digital frameworks.

2014 — 2018

BS, Criminal Justice

University of Southern California. Specialized in visual storytelling and narrative-driven brand strategy for global career development.