A consulting-led firm focused on responsible AI, automation, and Microsoft-aligned enterprise solutions.
ContextWorks Digital Systems is a Microsoft-focused consulting firm serving organizations in healthcare, legal, accounting, and enterprise IT. We specialize in AI adoption, workflow automation, and governance frameworks for regulated and professional environments.
Unlike development agencies that build what you ask for, we function as strategic advisors—helping you determine what should be automated, what risks exist, and how to implement solutions that your team can maintain long after we’ve completed the engagement.
We work exclusively within the Microsoft ecosystem because depth of expertise matters more than breadth of tools. When your organization runs on Microsoft 365, your AI and automation strategy should leverage that foundation—not introduce fragmentation with disconnected platforms.
ContextWorks is led by senior architects with over 15 years of experience designing and implementing enterprise solutions within the Microsoft ecosystem—from on-premises SharePoint and Exchange to modern Azure cloud architectures.
Worked across the full evolution of Microsoft’s platform—SharePoint 2007, Exchange Server, Azure infrastructure, Power Platform, and Azure AI Services. This longitudinal experience informs how we architect for longevity and maintainability.
Experience designing solutions for healthcare systems, legal practices, accounting firms, and corporate IT teams—environments where compliance, auditability, and risk mitigation are non-negotiable requirements.
AI is a tool, not magic. It requires governance, human oversight, and clear understanding of its limitations. Our approach prioritizes responsible implementation over rapid deployment, ensuring solutions are safe, compliant, and maintainable by client teams.
When you engage with ContextWorks, you work directly with experienced architects—not junior developers or offshore teams. This is deliberate: trust-based consulting requires senior judgment and accountability.
Mid-size professional service organizations face a critical challenge: they need AI and automation to remain competitive, but they cannot afford to experiment with data security, compliance posture, or operational risk.
The market offers two extremes: enterprise consultancies with six-month timelines and seven-figure price tags, or offshore development shops that build whatever you ask for without questioning whether it’s the right approach.
ContextWorks was founded to address this gap—providing senior-led, Microsoft-aligned consulting with fixed-scope engagements, clear deliverables, and a focus on responsible AI adoption in regulated environments.
We exist to help organizations adopt AI and automation safely, strategically, and sustainably—without hype, without vendor lock-in, and without compromising the trust relationships that define professional services.
Fifteen years of platform evolution, from on-premises infrastructure to cloud-native AI services.
From SharePoint 2007 to Azure AI Services, we’ve architected solutions across the full evolution of the Microsoft stack.
Deep understanding of Azure security, identity management, and AI services for enterprise-grade solutions.
Certified expertise in Power Automate, Power Apps, and Copilot Studio for low-code automation.
Native integration with SharePoint, Teams, Outlook, and Dynamics 365 for seamless workflows.
We’re consultants who build solutions, not developers looking for projects. That distinction shapes everything we do.
Technology is the enabler, not the goal. We focus on the processes that consume your staff’s time and the workflows that slow your operations.
Your internal team needs to understand and support what we build. We create documentation, provide training, and avoid over-engineering.
If AI isn’t the right solution, or if an off-the-shelf tool meets your needs, we’ll tell you. We’re here for long-term relationships, not short-term revenue.
No open-ended development contracts. We define deliverables, timelines, and pricing upfront so you know what to expect.
AI is a powerful tool, but it requires thoughtful implementation—especially in industries handling sensitive data.
AI assists, humans decide. We design solutions that augment staff capabilities, not replace human judgment in critical decisions.
Data encryption, role-based access, and audit logging are standard in every solution we build, not optional add-ons.
We understand HIPAA, GDPR, and industry-specific regulations. Our solutions are designed with compliance considerations from day one.
Every AI interaction is logged. Every automated decision can be traced. You maintain full visibility and control.
We respect professional ethical obligations—whether that’s attorney-client privilege, patient confidentiality, or CPA independence standards.
We explain how AI works, what its limitations are, and how to use it responsibly. No black boxes.
We serve clients across the United States, United Kingdom, and Australia. Our delivery model is designed for distributed collaboration with security and compliance at the core.
All engagements can be delivered remotely, reducing costs and timelines while maintaining quality and security.
We accommodate client time zones for discovery calls, training sessions, and support across multiple regions.
Familiarity with data protection regulations including HIPAA (US), GDPR (UK/EU), and Privacy Act (Australia).
All client communication and document sharing through Microsoft Teams and SharePoint with enterprise-grade security.
These principles guide every engagement, architecture decision, and client relationship.
We're a senior-led consultancy, not a large agency. You work directly with experienced architects, not junior developers.
We deliver well-architected solutions over rushed implementations. Better to do it right than do it fast.
We explain things in business terms, not technical jargon. If we can't explain it clearly, we shouldn't build it.
We measure success by your outcomes, not by the number of hours billed or features shipped.
If you're evaluating Microsoft AI, Power Platform, or Azure solutions, we'd be happy to share our perspective. No obligation—just a conversation about your specific situation.
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