Our Story

About ClearPoint Technology Services

Veteran-founded. Practitioner-led. Built at the intersection of cybersecurity expertise and emerging AI capability — to serve missions that matter.

Who We Are

Practitioner-Grade Expertise. Mission-Focused Delivery.

ClearPoint Technology Services, LLC was founded on a simple premise: the organizations that need cybersecurity and AI services most — mission-critical enterprises and growing businesses — deserve consultants who have actually done the work, not just studied it.

Our founder brings over 25 years of hands-on GRC leadership, enterprise security program management, and emerging technology advisory experience to every engagement. We built ClearPoint Technology Services to be the firm we always wished we could hire — direct, accountable, and relentlessly focused on outcomes over optics.

As a Service-Disabled Veteran-Owned Small Business, we bring the discipline and mission orientation of military service to every client relationship. We don't just deliver reports — we deliver results.

Markets Served

commercial Civilian · Department of Defense · Commercial Enterprise

Why ClearPoint Technology Services

What Sets Us Apart

ClearPoint Technology Services is not a typical consulting firm. Here is what makes us different — in concrete terms.

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25+ Years of Practitioner Experience

Not a theory-based consultant — hands-on GRC leadership across healthcare, regulated industries, and enterprise retail. Results-driven, not compliance-theater. Every recommendation comes from someone who has lived the consequences of the decisions being made.

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Deep Operational Security Experience

Deep experience across healthcare systems, retail, financial services, and regulated industries. ClearPoint Technology Services understands how complex organizations operate from the inside — the culture, the constraints, and the business priorities that drive every security and technology decision.

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Enterprise GRC at Scale

Led the GRC function for Dollar Tree, Inc. — one of North America's largest retailers with 16,000+ locations. Direct experience managing PCI-DSS, third-party risk, vulnerability management, and NIST CSF implementation with regular C-suite and Board reporting. We know what enterprise-scale GRC actually looks like.

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AI + Security Integration

Uniquely positioned at the intersection of cybersecurity, GRC, and artificial intelligence. ClearPoint Technology Services delivers AI strategy and AI security services from a practitioner who understands both the opportunity AI creates and the risk it introduces — not just one side of the equation.

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Executive Communication

Regular C-suite and Board-level briefings throughout our career. We translate complex technical risk into business language that decision-makers understand and act on — because a finding that doesn't get addressed is a finding that doesn't matter.

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Service-Disabled Veteran-Owned Small Business

U.S. Army veteran with service-connected disability and a lifelong commitment to mission-driven work. ClearPoint brings that same discipline and accountability to every commercial and state/local government engagement.

Leadership

Founder & Managing Member

RG

Robert Green

Managing Member · U.S. Army Veteran

Robert brings over 25 years of cybersecurity, GRC, and technology advisory experience across healthcare systems, Fortune-500 enterprise environments, and state/local government organizations.

His career spans security program management at GSA, HUD, FAA, the State Department, enterprise Tricare, Marine Corps, Air Force, and Navy healthcare — followed by seven years leading the enterprise GRC function at Dollar Tree, Inc., one of North America's largest retailers.

Robert founded ClearPoint Technology Services to deliver the kind of direct, practitioner-led advisory and AI services that mission-critical organizations need — without the overhead and dilution of larger firms.

U.S. Army Veteran 25+ Years Experience
Track Record

Past Performance

A career built on delivering security and compliance outcomes for organizations where the stakes are real.

Dollar Tree

Dollar Tree, Inc.

Provided enterprise GRC program management for one of North America's largest retailers — 16,000+ stores across the US and Canada. Managed PCI-DSS compliance program, third-party risk management, vulnerability management, and NIST CSF implementation.

DOMA Technologies

DOMA Technologies

Provided FedRamp Security authorization and compliance framework implementation for a cloud SaaS platform. Developed System Security Plans (SSPs), implemented continuous monitoring programs, and coordinated assessment activities throughout the authorization process.

U.S. General Services Administration

U.S. General Services Administration

Contract supporting federal IT infrastructure compliance and Certification & Accreditation (C&A) activities for one of the federal government's primary acquisition and real property management agencies.

HUD Office of the CIO

HUD Office of the CIO

Provided Program Management overseeing Certification & Accreditation for federal information systems within the U.S. Department of Housing and Urban Development, supporting the agency's security compliance frameworks compliance posture.

Sentara Healthcare

Sentara Healthcare

Provided security compliance for large-scale healthcare information systems serving hundreds of thousands of end users across distributed environments.