Rakewood Advisory Group
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Practical Technology Risk Guidance - Scaled to the needs of your business 

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Why Rakewood Advisory Group?

Technology risk is business risk. Rakewood Advisory Group provides independent, principal-led technology risk advisory for small and mid-sized organizations that require objective guidance, not another delivery relationship.

Remote-first by design, we work with organizations across Canada to help leadership prioritize risk, strengthen governance, and reduce business disruption. We assist organizations in moving away from reactive checkbox security toward a resilient, risk-aware culture.

 

The Independent Advantage

Rakewood is structured specifically for independent advisory work and to avoid the conflicts common in vendor, managed service, and staffing models. Our methodology is efficient and grounded in international standards.

 

Modern Methodology

We recognize that small and mid-sized businesses operate with limited resources. While we utilize modern risk management platforms to replace outdated spreadsheets, we remain strictly independent. We provide the objective, senior-level counsel required to ensure security spending protects the bottom line and maintains operational stability.

Rakewood provides practical guidance focused on the interests of the organization, informed by decades of real-world client delivery experience.


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The Rakewood Advantage

Technology risk is not managed through software purchases, templated advice, or outsourced accountability. It is governed by experienced judgment, disciplined prioritization, and decisions aligned with business impact. Rakewood Advisory Group acts as an independent partner for technology governance. We provide the senior perspective necessary to protect your business while remaining free from the conflicts of interest found among traditional vendors.


Proven Expertise

Established on a foundation dating back to 2000, Rakewood draws on twenty-five years of expertise in technology architecture and specialized subcontracting for industry leaders in Canada’s banking, technology, automotive manufacturing, telecommunications, and electronics sectors. As a fully independent advisory practice, Rakewood is detached from product sales, managed service contracts, and staffing incentives. This ensures a focus on practical risk management and actionable steps tailored to your specific requirements.


Enterprise-Grade, Tailored for Small and Medium-Sized Businesses

Rakewood Advisory Group delivers enterprise-level standards to the small and medium-sized business sector. All engagements are led by a Principal Consultant with over thirty years of senior leadership experience directing teams, programs, and strategic initiatives for prominent international organizations. Supported by multiple certifications, including CISSP, our approach is built on seasoned judgment rather than templated checklists. At Rakewood we do not engage junior staff; every resource maintains a minimum of ten years of industry experience. This ensures your security strategy remains professional, verifiable, and appropriately scaled to your requirements.

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Glass building


Most small and mid-sized organizations do not need more tools. They need clear priorities, practical planning, and experienced guidance they can trust. Rakewood Advisory Group provides independent advisory to help leadership reduce disruption and make better technology risk decisions.


Our Services

Our engagements provide the senior perspective required to align technology risk with business objectives. We provide the documentation and practical priorities necessary to satisfy the requirements of partners and insurers.



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Technology Risk Counsel

Rakewood's risk advisory model provides senior-level expertise to guide the organization in managing technology risk as a fundamental business priority. Rakewood acts as your independent advisor, ensuring that leadership has the oversight and methodology required to maintain an effective security posture.

  • IT GRC Foundations and Advisory Oversight: We establish the framework for Governance, Risk, and Compliance. This involves the selection and guidance of technical and administrative controls. We provide the oversight necessary to ensure your security posture is substantive and verifiable, allowing the organization to demonstrate control effectiveness over time.

  • Compliance Strategy and Acceleration: We provide the guidance required to build policies and control frameworks that accelerate readiness for SOC 2, ISO 27001, or NIST-based standards. By establishing clear accountability, we ensure you have the documented evidence necessary to satisfy the inquiries of partners, customers, and insurers.

  • Executive Decision Support: We translate technical exposures into business-level context. We provide the senior perspective necessary for leadership to make informed decisions that protect business continuity and the bottom line, focusing on the priorities that matter as threats and business demands evolve.


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Professional Services Engagements

Engagements delivered on a project basis to address specific requirements, improve readiness, and reduce the impact and likelihood of business disruption.

  • Control Maturity Assessments: Evaluation of technical controls against recognized benchmarks such as the NIST Cybersecurity Framework and CIS Critical Security Controls. This process identifies gaps between current practices and industry standards to provide a clear baseline for improvement.

  • ISO-Aligned Technology Risk Assessments: Formal analysis of business impact utilizing methodologies aligned with ISO 27001, ISO 27005 and ISO 31000. These assessments identify specific scenarios that could disrupt the organization, providing the framework to reduce the likelihood and impact of adverse events.

  • Cyber Risk Awareness and Culture: Development of a security culture rooted in shared responsibility. Establishing a professional rationale for security transforms the workforce into a detection layer, accelerating response to incidents and zero-day threats while mitigating the impact of social engineering.

  • Insurance and Questionnaire Support: Senior guidance to accurately complete cyber insurance applications and customer security questionnaires. This includes the preparation of supporting documentation aligned with documented IT practices.

  • Vendor and Partner Security Reviews: Detailed review of vendor questionnaires and partner technology practices to identify third-party and Nth party risks that could disrupt business continuity or expose sensitive information.

  • Incident Response and Threat Readiness: Advisory oversight for the incident response program, including the design of bespoke tabletop exercises and the review of response plans. This prepares leadership for the strategic decisions required during a disruptive event or material incident.

  • SOC 2 and ISO 27001 Readiness: Guidance on control development, governance, and process alignment to prepare the organization for SOC 2 Type I/II and ISO 27001 readiness efforts.

  • AI Governance and Responsible Use: Guidance on the secure adoption of Artificial Intelligence through the development of policies, practices, workflows and guardrails aligned with ISO 42001 and the NIST AI Risk Management Framework  to support safer use of tools such as Microsoft Copilot, identify Shadow AI, and reduce data exposure risk across the organization.

  • Legacy Platform Risk Management: Development of risk reduction strategies for unsupported or aging IT systems when replacement is not yet practical. This includes implementation of compensating controls to mitigate exposure.

 

Let Us Help Safeguard Your Business


Book a discovery session to identify your highest technology risks, set priorities, and build a practical plan to reduce the likelihood and impact of business disruption.

Book an AppointmentBook an Appointment

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Get in touch


Rakewood Advisory Group Inc. welcomes direct inquiries regarding principal‑led advisory engagements.


Rakewood Advisory Group Inc.

External link opens in new tab or window1-888-791-8120 |  Info@RakewoodAdvisory.com
250 Queen Street, PO Box 1282
Port Perry, Ontario
L9L 1B9

190970
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