Automations.Guru
Automate with confidence

Structure. Automation.
AI. In that order.

Most AI projects stall because the foundation isn't ready. I fix the data and process layer, automate the workflows, then deploy AI on clean, governed information — so it works the first time.

20+ years across five platform waves Microsoft Partner
1
Structure
Fix the data + process layer. Clean, classify, govern.
2
Automation
Automate the repetitive work on a clean foundation.
3
Artificial Intelligence
Deploy AI & agents on governed information — dependably.
1 PB+
data migrated lifetime
~20 yrs
enterprise Microsoft 365
52 TB
migrated in a single year
100s
of SharePoint migrations
$60K+
on Upwork · Top Rated Plus
What we do

AI is the substrate. Everything else makes it reliable.

Ten offerings across four clusters — each in deliberate order: AI, automation, Microsoft 365, then Google Workspace.

AI & Context Engineering

Structure your business so AI becomes dependable — deterministic engines, document extraction, and your expertise encoded into agents.

Agents & Automation

Orchestrate AI agents like a project, not a chatbot. Automate the repetitive work — from Power Automate flows to multi-day agent builds.

Migration & Governance

Petabyte-scale migration into Microsoft 365, plus the governance — permissions, retention, Copilot readiness — that keeps it clean.

Cost & Local AI

Cut the AI bill through model routing, and host private, data-sovereign AI for clients who can’t send data to the cloud.

How we work

Structure, then Automation, then AI

Most AI projects fail at the foundation, not the AI. We work in a deliberate sequence — the same one I’ve lived across two decades. It isn’t a slogan; it’s the order reality demands.

01
Structure
Fix the data and process layer first. Clean, classify, and govern your information so it’s reliable. Often "build me an AI assistant" is really "fix your data foundation first."
02
Automation
Automate the repetitive workflows on that clean foundation — provisioning, routing, reporting, filing — with audit trails and human approval gates.
03
AI
Only then deploy AI and agents, on clean and governed information, where they’re dependable instead of a slot machine.
Shape tech around the business
We don’t cram you into a platform — Microsoft, Google, or pen and paper.
Discovery-first, no assumptions
Every decision backed by facts from structured discovery, not guesswork.
Security & compliance by default
Least privilege, minimized PII, DLP and retention enforced.
Leave you self-sufficient
Train-the-trainer, internal admins, as-built runbooks — not a dependency.
Documentation that enables
Plain-English, diagram-led, executive-ready. "Clients don’t buy CSVs. They buy clarity."
No destructive action without evidence
Every change is evidence-backed and approved before anything is touched.
Services

Ten ways to make AI actually work

Each offering: the pain it solves and what gets delivered. Proof lives in the work.

Make AI a Reliable Tool

PainYou bought AI and got a chatbot you argue with.

Deterministic, multi-pass AI engines over a modular knowledge base with validation gates — AI that behaves like software, not a slot machine.

Read the Dense Documents for You

PainTeams burn hours comparing 80+ page regulated documents.

Engines that extract and compare dense documents with page-cited evidence and zero hallucination — every field tagged with value, page, and confidence.

Clone Your Best Expert

PainYour business depends on one or two experts who can’t scale.

We encode an expert’s workflow and judgment into agents that deliver it at scale, under guidance. (I did it to myself first.)

Automation in practice

What we actually build

Real patterns from recent work — anonymized. AI with guardrails, approval gates, and observability baked in; not demos. The same principle every time: structure and govern first, then let automation and AI run on top.

AI review-reply engine

Drafts replies to Google reviews in the client’s voice, sentiment-routed — high ratings auto-post, low ratings hold for human approval, with a safe neutral fallback after 72h. Fully logged and observable.

Make.comOpenAIAirtableGBP APIMailgun

Document-AI quote comparison

A multi-agent engine that extracts and compares multi-year insurance policy PDFs using a field dictionary, page-classification rules, and a core orchestrator — structured output a human can trust.

OrchestratorExtraction rulesGPTPDF parsing

Custom GPTs grounded in your data

Knowledge-base assistants for proposals, scoping, and portfolios with strict zero-assumption data rules — exact figures only, no filler, human-readable output that doesn’t read like a bot.

Custom GPTKnowledge basePrompt design

Tenant-to-tenant at scale

Mailboxes, OneDrive, hundreds of SharePoint sites and dozens of Teams migrated across tenants with metadata, permissions, and chat history intact — staged, scripted, and batched.

ShareGateMovebot.ioGraph APIPowerShell

Forms & process modernization

Legacy Gravity Forms and Google Forms rebuilt as SharePoint lists driven by Power Automate — metadata-structured intake, approvals, notifications, and clean API integration where needed.

Power AutomateSharePointPower AppsFastAPI

Teams Phone & Voice

Auto attendants, simultaneous-ring call queues, shared transcribed voicemail, and caller-ID policy — inbound and outbound behavior validated end to end across the team.

Teams PhoneAuto AttendantCall Queue
Working stack — Make.com · Airtable · OpenAI · Power Automate · Graph API · PowerShell · ShareGate · Mailgun · JotForm · Google Workspace
Selected work

Two decades of real, shipped projects

A sample from the portfolio — current Microsoft 365 engagements alongside enterprise migrations, modernizations, and governance across legal, utilities, education, manufacturing, and nonprofits. Concrete scope, no fluff.

Boutique law firmActive · 2025

Microsoft 365 modernization & case-workflow automation

Replaced paper-based legal processes with secure digital ones: Teams as the daily hub, metadata-driven SharePoint case libraries, and Power Automate for intake, notifications, and approvals — with training and phased rollout across the partners.

100%paper workflows replaced
TeamsSharePoint OnlinePower AutomatePurview
K-12 public school districtEducation

SharePoint Server 2019 → Entra ID modern authentication

Migrated 76,000 accounts across 2,500 site collections and 11,000 subsites to Entra ID with EntraCP, re-permissioning 8M+ objects via staged, parallel-batch automation — a coordinated 5-day cutover with full auditability.

76,000users to modern auth
PowerShellGraph APIEntra IDEntraCP
Electric transmission utilityUtilities

Embedded SharePoint architect & infrastructure automation

Led the $4M DTS for secure, regulated external data exchange under zero-trust compliance; automated 80%+ of patching, builds, and provisioning; designed a SQL Always On HA backend with hybrid auth (Azure AD Connect, ADFS, App Proxy).

$4MDocument Transmittal System
SharePoint 2016SQL Always OnNintexPowerShell
Global consumer-goods brandConsumer Goods · 2025

Microsoft 365 tenant-to-tenant migration

Migrated several hundred users across tenants — mailboxes, OneDrives, and identities — alongside several hundred SharePoint sites and dozens of Teams, preserving chat history, membership, and integrated resources.

100ssites + dozens of Teams
ShareGateMovebot.ioExchange OnlineTeams
Precision-manufacturing groupManufacturing · 2025

Tenant consolidation & collaboration modernization

Consolidated two tenants after an acquisition: OneDrive for hundreds of users plus SharePoint Online sites and libraries migrated with metadata, structure, and permissions intact via ShareGate scripting and staged batch processing.

Hundredsusers migrated T2T
ShareGatePowerShellOneDriveSharePoint Online
Energy & land-management firmEnergy · 2025

SharePoint security audit + Exchange retention cleanup

Tenant-wide access and oversharing audit with a risk register and remediation framework; analyzed 6,000+ mailboxes for DiscoveryHold and obsolete hold tags, then removed stale retention data at scale with safety-checked PowerShell.

6,000+mailboxes remediated
PowerShellImportExcelGraph APIPurview
Global chemical manufacturerEnergy & Chemicals

SharePoint 2013 farm modernization to governed, Teams-integrated SharePoint Online

Modernized a legacy SharePoint 2013 environment and scattered file-share content into a governed, Teams-integrated SharePoint Online architecture — discovery, taxonomy, and permissions redesigned across the estate, migrated in phases with automation and validation, then the legacy farm decommissioned.

13,000+SharePoint sites modernized
SharePoint 2013SharePoint OnlineTeamsPowerShell
Healthcare organizationHealthcare · Public Service

SharePoint intranet farm implementation, migration & upgrades

End-to-end SharePoint delivery for a healthcare organization: requirements, architecture, provisioning, migration, upgrades, security, and governance, with training and support carried through to ongoing operation.

Full lifecyclerequirements to ongoing support
SharePoint 2019GovernanceSecurityTraining
Professional-services firmEmail security

Custom DMARC connector for Exchange Online with automated failed-validation reporting and ITIL-aligned incident runbooks.

Law firmLegal services

Power Automate workflow bridging SharePoint approvals to client FastAPI endpoints for document reindexing — fixed-fee, 7 business days.

Regional nonprofitNonprofit

Compliance-grade Microsoft 365 & Exchange recovery after a failed vendor-led migration.

Industrial distributorManufacturing

Legacy Linux CMS → Microsoft 365; 1.5 TB archived, 20+ intranet pages rebuilt with PnP provisioning.

Emergency healthcare providerHealthcare

Accelerated SharePoint 2013 → Online migration of an unsupported farm, then a safe decommission.

Private clientProfessional Services

SharePoint Online project-workspace provisioning & lifecycle governance — setup cut from hours to minutes.

Accounting firmProfessional Services

Metadata-driven SharePoint reindexing pilot — 84 staged files, 1,680 of 1,680 metadata values matched on validation, zero mismatches.

Healthcare providerHealthcare

SharePoint intake and file-automation architecture — eight libraries and 65 operational views, validated against 22 of 22 synthetic test scenarios.

Oil & gas producerTeams Voice

Migrated 500+ users from legacy PBX to Teams Phone via Direct Routing, with automated provisioning cutting admin effort by over 60%.

Energy companySecurity audit

SharePoint access and oversharing audit — 74 site collections reviewed, 200+ stale accounts cleared, 188 overshared documents remediated.

Home care providerHome Care

Multi-location Microsoft 365 environment brought under consistent structure, permissions, and governance.

Nonprofit organizationTenant separation

Split a subsidiary cleanly out of a parent Microsoft 365 tenant — mailboxes, Teams, and SharePoint — during a business-critical holiday freeze window with zero significant downtime.

About

The tool changes. The expertise doesn’t.

I’m Matt Chapple — a Microsoft 365 architect and AI/automation consultant with ~20 years across enterprise and public-sector environments: SharePoint modernization, petabyte-scale migration, Copilot readiness, and PowerShell-driven automation. I build secure, governed platforms organizations can confidently build AI on.

What’s special about Automations.Guru isn’t the brand — it’s the person. The company is the storefront; I stay on the glass; agents and a trusted collective deliver behind me. Across five platform waves the move never changed: take what’s in front of you, intake it, structure it, process it, and shape it to its maximum.

MC
Matt Chapple
Founder · Airdrie, Alberta
Microsoft Partner

"Tell me who you are, what works, what doesn’t — I’ll shape your ecosystem around you, so you’re not cramming yourself into the technology."

20+ years · five platform waves
2000s
Infrastructure
Windows, SQL HA/DR, networking — the full-stack foundation. Tier 1 NOC to running SharePoint & Exchange for two of Canada’s largest oil & gas companies.
2007 → 13
SharePoint
Became "The SharePoint Guy" the market named — ~30 enterprise SharePoint 2010 implementations, full-stack admin and architecture.
2020
The pivot
When the cloud went SaaS, infrastructure stopped being the product. Climbed a layer — to process, governance, automation. "Infrastructure never dies. It moves up a layer."
2020 → 23
Migration
The petabyte era — extract from anywhere, reshape into SharePoint, tag it. PowerShell, ShareGate, PnP. The earned origin of the "Guru."
2023 → 24
Governance
Purview, DLP, conditional access, tagging — the foundation Copilot would land on. "Structure, then Automation, then AI" is the sequence I lived.
2024 →
AI & agents
Context engineering, agent orchestration, a self-hosted agent OS. Went independent as Automations.Guru; became a Microsoft Partner.
Recommendations

In their words

Verbatim LinkedIn recommendations from the architects, PMs, and consultants who've shipped alongside me across two decades.

5.0★★★★★
97%client satisfaction
Top Rated PlusVerified on UpworkView Upwork profile ↗

“Matt was amazing and gave all the details I required in a concise and understandable manner. Highly recommend!”

Verified Upwork review · Mar 2026

“Matthew was wonderful to deal with. I would definitely recommend his services. He was able to help me with my Outlook and OneDrive issues.”

Verified Upwork review · Jul 2025
Clear CommunicatorDetail OrientedCollaborativeSolution Oriented

I worked with Matt on one of the most challenging projects I have ever managed — a $4 million multi-year cloud-based SharePoint initiative with profound regulatory and cybersecurity implications. When it comes to SharePoint, Matt is like a ninja that went to top-gun school and graduated with honors!

FG
Fred Guzman
PMP, CISSP · Project Delivery Expert

I worked with Matt on various large enterprise SharePoint and MS Teams migration projects at Habanero, where Matt was the lead Infrastructure Architect. Matt is a natural leader with strong technical ability and a unique skill of engaging all stakeholders to ensure blockers are removed and goals are achieved on time and on budget. He has very sophisticated knowledge of migration projects and M365 applications and ensures he spends time teaching others alongside him. If I was to pick a team for any project, Matt would be on that list!

FA
Fraser Allan
Business Consultant · Habanero

Matt was my senior go-to resource for implementing or resolving challenging SharePoint and SQL solutions.

SC
Shane Crawford
Director, Cyber Security & Enterprise Architecture · DevFacto

Matt helped us with our first implementation of SharePoint. He was very knowledgeable and always willing and quick to help.

MG
Mina Gould
Senior Business Analyst · belairdirect

Matt was a pleasure to work with! He has an amazing amount of knowledge and was great at sharing it. I would work with Matt anytime!

JS
Jose Samayoa
IT Manager · Western Tractor Company

Matt is dedicated, conscientious, very competent and enthusiastic who always sought out ways to improve delivery and make work more efficient.

BJ
Bruce Johnston
President · Iron Condor Innovations

Matt is a phenomenal Microsoft 365 architect who is client-centric, competent, easy to work with, well-versed in content migrations, and excels in problem-solving.

BD
Benjamin Dorge
Technical Writer & M365 Analyst · Habanero

Matt is very skilled, organized, down-to-earth and friendly with a very methodical way of thinking through any project or task. I would highly recommend Matt to anyone!

RS
Richard Singh
Senior Technical Architect · Azure & D365

Working with Matt was always a great experience — a great blend of problem solving and cost management. Very easy to work with, awesome personality and always available to help out!

RK
Ryan Kazmerik
Product & Engineering Leader · Data Science & AI

Matt was the go-to person for SharePoint infrastructure, scripting and SQL! He helped me resolve a number of complex SharePoint issues. He knows his tools quite well and is very knowledgeable!

WF
Wisam Fawzi
Principal Power Platform & SharePoint Consultant · DevFacto

Matt has amazing technical skill and knowledge. He is able to break down complex problems quickly. We were able to complete challenging projects because of his skill set. When selecting a team I always ask for him by name!

AA
Alvaro Albanez
Cloud Architecture & Cyber Security

Matt has very deep SharePoint understanding — a wonderful professional and excellent person. He focuses on client needs and gets issues resolved. I have seen him on very complex projects and he always brings the right answer. I recommend him!

AR
Anaidy Ruiz Hernandez
M365 Certified Enterprise Admin Expert

Working with Matt was a very positive experience. He was most instrumental in helping design, implement and support a new and very complex SharePoint environment. As a Subject Matter Expert, Matt has a keen sense of analysis and a solid ability to provide working solutions. I would gladly work with him again.

EO
Ete Ometoruwa
Tech Architecture Manager · Accenture
FAQ

Straight answers on SharePoint, scale, and AI

The questions buyers actually ask — answered from the real portfolio, counted honestly, with no marketing rounding.

Conservatively, more than 30 enterprise SharePoint implementations over my career — without inflating the number by counting individual sites, libraries, migration waves, or stand-alone support engagements as separate implementations. I also distinguish full implementations from upgrades, audits, recovery work, advisory work, and prototypes.

Knowledge and document management, intranets, enterprise search, governance, migration, and adoption have been recurring core components of that work for more than twenty years — from focused departmental repositories to enterprise programs spanning thousands of sites.

By content volume: 52 TB across more than 30 departments for a global consumer-goods brand — discovery, stakeholder workshops, information architecture, metadata, permissions, governance, phased migration, delta passes, validation, UAT, training, and handoff.

By structural scale: a global chemical manufacturer — an estate of more than 13,000 SharePoint sites plus file-share content, modernized from SharePoint 2013 into a governed, Teams-integrated SharePoint Online architecture.

These were not file-copy projects; they were end-to-end architecture, governance, migration, validation, and adoption programs. And raw storage is only one measure of complexity — in my experience an unstructured library or operating view becomes impractical at roughly 100,000 items, long before the platform's theoretical limits.

The most common one: treating SharePoint as a network drive in a browser — reproducing a deep folder tree inside one enormous library and expecting search, automation, or Copilot to make it usable. Other recurring mistakes:

  • Designing a polished interface before fixing the information architecture.
  • Building sites around the org chart instead of ownership, audience, sensitivity, and lifecycle.
  • Migrating duplicates, stale versions, and broken permissions without remediation.
  • Relying on direct sharing and item-level permission exceptions.
  • Treating search as a search-box problem instead of a content-quality and metadata discipline.
  • Deploying flows and custom components with no source ownership, monitoring, or support owner.
  • Big-bang migrations without pilots, reconciliation, delta passes, and rollback criteria.
  • Enabling Copilot or AI before authoritative content and permissions are trustworthy.

I avoid these by inventorying the real environment first, mapping the user journeys the repository must support, preserving what works, correcting the weakest foundational layer, and validating with representative content and permission scenarios before scaling.

Yes — at the tested-prototype and AI-readiness level, not as a tenant-wide production SharePoint AI rollout.

In one Microsoft 365 Copilot engagement, I mapped a consulting organization's SharePoint and Teams knowledge model, translated a real compensation-change process into structured agent instructions, created Copilot-ready templates, and built and successfully tested a focused business agent — defined knowledge documents, task-specific instructions, controlled draft outputs, and human approval points, with a roadmap for Power Automate integration.

Across separate Copilot-readiness engagements I have organized authoritative knowledge, addressed permission and oversharing risks, and designed repositories to become reliable AI grounding sources — and I describe advisory designs and prototypes as exactly that, never as production deployments. My preferred pattern keeps SharePoint as the governed source of record, limits AI to approved knowledge, points users back to source material, and keeps consequential actions behind explicit rules and human approval.

My operating principle: Structure. Automation. AI. In that order. The practical sequence:

  1. Inventory sites, libraries, owners, volumes, permissions, sharing links, search, customizations, and authoritative sources.
  2. Validate permissions, remediate oversharing, and move to group-based least privilege with named owners.
  3. Separate working and draft spaces from approved, published, archived, and restricted knowledge.
  4. Remove or isolate duplicates, obsolete material, stale versions, and scans that need OCR.
  5. Establish intentional site purposes, a small useful metadata model, and source-of-truth signals.
  6. Make search dependable: indexing, titles, refiners, managed properties, and representative business questions.
  7. Establish ownership, review, retention, archive, sensitivity, and data-loss-prevention controls.
  8. Select one bounded AI use case — defined audience, approved sources, success measures, and conditions to decline to answer.
  9. Test expected answers, citations, permission personas, stale content, leakage scenarios, and adversarial prompts.
  10. Keep publishing, approvals, and consequential actions behind deterministic rules and human review.
  11. Monitor failures, unanswered questions, and repository health before expanding.

AI amplifies the state of the knowledge environment beneath it. In a well-structured, authoritative repository it makes years of organizational knowledge dramatically more useful; in a duplicated, stale, overshared one it makes those weaknesses faster and more visible.

I would not claim to be better than every specialist at every individual technology. My advantage is the combination: principal-level architecture, hands-on implementation, quantified enterprise-scale experience, inherited-system recovery, evidence-based validation, automation, and current AI capability — plus the infrastructure, SQL, and authentication foundations beneath SharePoint.

I am comfortable taking over failed, incomplete, over-customized, or poorly documented environments: inspect the real system, reproduce the failures, preserve what is worthwhile, identify the layer that is actually wrong, and make the smallest coherent correction. I do not begin by selling a rebuild or the newest feature.

Enterprise scale matters, but proportionality matters too — you should not inherit architecture or overhead you do not need. The finished solution should be understandable, documented, validated, and owned by you, not dependent on the consultant who built it.

Contact

Tell us who you are.

Every engagement begins with discovery — no assumptions, no upsell. Just a clear read on what you actually need, whether you’re on Microsoft, Google, or pen and paper.

Let's talk.

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