Cloudwell Conversations: Chris Alechko on Building Modern, AI-Ready Architecture and Scalable, Automated Governance 

Kelvin Helmholtz (KH): As both co-founder and CTO of Cloudwell, how do you balance long-term vision with the day-to-day technical decisions needed to keep Cloudwell at the forefront of Microsoft 365 innovation?

Chris Alechko (CA): It’s a balance that hinges on alignment and architecture. As a small company, we constantly have dozens of active projects, but our long-term vision – which is deeply tied to the Microsoft Roadmap – must serve as the compass.

Day-to-day, I keep a close pulse on what our engineers are building to ensure we’re adhering to modern architectural principles and avoiding legacy platforms. If a client requests a solution that can be done more elegantly or sustainably using a newer service (like Power Platform or Azure Functions instead of older SharePoint Framework versions), we immediately present the pros and cons. This ensures our clients aren’t adopting solutions with a short shelf-life.

KH: You’ve worked in the Microsoft ecosystem for many years. How have you seen Teams and SharePoint evolve, and what does that mean for enterprise IT leaders today?

CA: The evolution of Teams and SharePoint signifies the complete dissolution of application silos. It used to be that work was application-centric: Outlook for email, SharePoint for documents/intranet, and a separate platform for chat. Today, the work is data-centric and user-flow-centric.

Users can now seamlessly access their documents, calendar, and collaboration tools from any endpoint—be it Teams, Outlook, or SharePoint. This shift is enormous, and for enterprise IT leaders, it means their governance and security strategy must be platform-agnostic. The focus must move from where the data is stored to how the user interacts with that data across all M365 touchpoints.

KH: When you talk with Cloudwell customers, what are the most common challenges they’re facing in Microsoft 365 environments? Are those challenges more about technology, governance, or user adoption?

CA: In the current landscape, the challenges are fundamentally a trio of interconnected issues, though the emphasis has shifted.

The technology itself is less of a hurdle than it was years ago. Microsoft has made M365 robust and highly accessible. Today, the focus has swung decisively to governance and user adoption. Without a coherent governance plan – defining what apps to use, when to use them, and who can access them – user adoption becomes toxic. You end up with app sprawl where some power users embrace everything, while most knowledge workers suffer from decision paralysis (e.g., “Should I chat here or send an email? Store this document in a Team site or OneDrive?”).

When we engage with customers, our priority is to guide the IT team in setting up a scalable, secure governance structure tailored to their organizational needs. We then ensure any new apps and customizations we implement are the right fit and scale. Lastly, we engage stakeholders to develop the training and change management expertise needed to effectively communicate why and how new tools should be used, securing long-term adoption and value realization.

KH: How is Cloudwell helping organizations address those challenges at scale? What approaches have you seen work particularly well for IT leaders managing complex M365 environments?

CA: We address these challenges at scale through two primary approaches: Architectural Modernization and Governance as a Service (GaaS).

Many large enterprises have years of accumulated SharePoint or legacy M365 debt. We specialize in migrating, consolidating, and modernizing these environments into a clean, modern architecture built on Azure and the Power Platform. This eliminates technical sprawl and centralizes management.

For IT leaders managing complexity, static governance documents fail quickly. We implement a GaaS framework that treats governance as an ongoing, automated process. This includes Automated Lifecycle Management where we use Power Automate and Azure Functions to automatically archive stale Teams, SharePoint sites, and Power Apps.

With Centralized Provisioning we implement tools that force users to use approved templates and security settings when provisioning new workspaces (e.g., a “Request a Team” solution).

Visibility is also key. Providing dashboards built on Power BI gives IT leaders a continuous, real-time view of usage, compliance, and sprawl risk across the entire M365 tenant.

The most successful approach we’ve seen is transforming IT from being the “policeman” to the “enabler”. By automating guardrails, IT leaders can safely delegate some control to users, speeding up innovation while keeping the environment secure and tidy.

KH: Shadow IT has long been a concern for CIOs and CTOs and now shadow AI is emerging. How should enterprises address these risks without stifling innovation?

CA: The key to combating both Shadow IT and the emerging Shadow AI is shifting the focus from blocking to providing a safer, better-governed alternative.

Shadow IT happened because corporate IT was too slow to deliver tools. Shadow AI happens because employees use public, ungoverned AI tools (like public LLMs) to process proprietary data, posing massive security and data leakage risks.

Enterprises should adopt a “Centralized Innovation Hub” strategy to provide a controlled AI environment. Using platforms like Azure OpenAI Service or Azure AI Studio allows users to access powerful LLMs while guaranteeing that the organization’s data is not used for model training. This removes the biggest barrier to using corporate-non-approved AI.

In addition, every AI tool, whether custom-built or third-party, must integrate with Microsoft Entra ID (formerly Azure AD). This ensures that only authorized users can access the AI, and importantly, that the AI itself operates under a defined identity and set of permissions.

We also recommend encouraging departments to build custom AI solutions using Copilot Studio and the Power Platform. This environment is inherently secure, subject to tenant policies, and provides the agility users need to innovate, pulling the shadow work out of ungoverned public apps.

The rule is to make the approved path the path of least resistance.

KH: There’s a lot of attention on AI for customer-facing functions, but research shows the back office is where many of the biggest productivity gains lie. Do you think enterprises are striking the right balance?

CA: No, I don’t believe most enterprises are striking the right balance yet, but they are rapidly pivoting. The initial hype and investment focused on customer-facing AI, for example AI-powered chatbots and sales assistants, because the return on investment is easier to measure – increased sales, lower support costs etc.

However, the true transformation potential is internal, in the back office. The largest gains come from automating repetitive, high-volume tasks that consume employee time, such as document processing, knowledge management and code generation.

Cloudwell’s focus is on deploying AI solutions that target this internal productivity. We are demonstrating to CTOs that a single back-office automation solution, like an AI that processes every incoming vendor request, can free up dozens of employee hours, providing an ROI that often dwarfs the gains from a public-facing chatbot. The balance is shifting as IT leaders realize internal efficiency is the prerequisite for external agility.

KH: With Microsoft introducing new tools like Entra Agent ID and Purview, how should CTOs think about governance and security for both people and AI agents in Teams and SharePoint?

CA: CTOs must adopt a mindset that AI agents are equal participants in the security model, not just tools. Every AI agent, custom Copilot, or automated workflow needs its own identity and governance perimeter.

Entra Agent ID is a game-changer. While this service is still in preview, it allows infosec managers to apply the principle of Least Privilege Access (LPA) to the agent itself. An invoice-processing AI should only have access to the accounting folder; it should be blocked from HR data. This prevents agents from accidentally or maliciously accessing unauthorized data.

Microsoft Purview is the enforcement layer. It must be configured to monitor and classify data accessed by AI agents just as it monitors human users. This includes Data Loss Prevention (DLP) and audit trails.

The takeaway is simple: Govern AI agents the same way you govern human users, using the dedicated identity and governance tools provided by Microsoft.

KH: From your perspective, how is the role of the CTO changing in this era of rapid AI adoption and digital transformation? What skills or mindsets will be most critical for future CTOs?

CA: The role of the CTO is evolving from a person who implements technology to someone who is a strategic architect and risk manager for the organization.

In the past, a CTO’s job was largely about selecting the best software and hardware. Today, with cloud platforms abstracting infrastructure, the CTO’s focus is on how to organize data, architect solutions that leverage AI as a foundational layer, and manage the associated risk.

The most critical skills and mindsets for future CTOs will be understanding how to centralize, cleanse, and structure organizational data to make it useful for AI models. AI is useless without good data.

CTOs must lead the conversation on the ethical use of AI, managing AI bias, and establishing the security perimeters for AI agents.

They need to know when to buy a SaaS solution, when to build a custom solution in Azure, and most importantly, when to use low-code/no-code platforms like the Power Platform to achieve rapid ROI and business agility.

The most profound changes today are cultural. The CTO must champion digital transformation, manage the fear surrounding AI, and drive user adoption across the entire organization.

KH: What technology trends do you think will most shape enterprise collaboration and productivity over the next 2–3 years?

CA: The next two to three years will be shaped by the convergence of three major trends: Contextual AI, Fluid Workspaces, and Semantic Search.

AI will move beyond simple chat prompts. It will become a passive, deeply integrated layer that understands your context and acts autonomously. For example, a Copilot will not just summarize a meeting, it will automatically draft follow-up tasks in Planner and flag relevant documents in SharePoint without a specific prompt.

Collaboration will shift away from static files and long email threads toward highly portable, real-time, atomic components. Microsoft Loop components will become the standard for collaboration, allowing elements of a document or task list to live in an email, a Teams chat, and a Loop page simultaneously, eliminating version control issues. At Cloudwell, we use Loop on a daily basis, and we are recommending that our clients do the same.

Search within M365, powered by Microsoft Graph and AI, will transition from keyword matching to semantic understanding. Users will ask complex, natural language questions, for example, “Find the policy about customer data retention that Jane mentioned last month”, and receive a precise, summarized answer, rather than a list of documents. This will be the single largest boost to knowledge worker productivity.

KH: What excites you most about Cloudwell’s future and how do you see the company continuing to help IT professionals get the most out of Microsoft 365?

CA: What excites me most is our position at the intersection of AI, security, and the unified M365 platform. We are no longer just building apps; we are architecting the secure, intelligent digital workplaces of the future.

We see two major opportunities that will define our future and how we help IT professionals. Firstly, enabling secure AI adoption. We are uniquely positioned to help IT professionals move beyond AI piloting to production AI deployment. This means implementing the governance policies, Entra Agent ID controls, and secure data pipelines, using Microsoft Fabric, required to make AI truly safe, scalable, and compliant within highly regulated environments.

We are also channelling our deep consulting expertise into our product suite. Our goal is to offer pre-built, modern, and highly governed solutions that solve common enterprise problems – like advanced governance or complex staff directory functionality – by leveraging the single-codebase model we discussed. This allows IT professionals to rapidly deploy best-in-class solutions that are guaranteed to comply with Microsoft’s roadmap, freeing them up to focus on strategic business initiatives rather than maintenance.

The future of M365 is one where the platform becomes an intelligent, automated partner. Cloudwell will be the firm that helps IT leaders build the secure, custom foundation needed to make that partnership a reality.

Are you an IT leader looking to form an intelligent, automated partnership with M365? Reach out to the experienced Cloudwell team to get started.