Michael Daugherty
Principal AI-Native IT Engineer · Internal Apps, Integrations, Automations and Administration
248-906-8367 · michaelservices.net · U.S. Citizen, Florida · Flexible hours · Remote
$125/hr · no retainer, no minimum
Twenty years building and running technology for other people's companies, much of it inside SaaS products, from streaming and ordering platforms to leasing and communications, now executed with an AI-native toolchain. I design the system, build it, and document it so nothing depends on me afterward. The speed comes from spec-driven AI development, practiced on my own AI-first custom applications built end to end; the judgment comes from Microsoft 365, Entra ID and Graph API work across a dozen enterprise environments.
Eleven in IT operations and managed services, nine building SaaS and custom software.
NIST 800-171 controls and assessment objectives in the Squared Away scoring engine, weighted on the DoD SPRS v1.2.1 methodology.
Technical skills
Consulting and platform engagements
Custom internal applications, AI automation and integrations, and hands-on technical leadership for small and mid-sized businesses.
- Built Squared Away, a CMMC Level 2 readiness platform for defense subcontractors, for a client: the scoring engine covers all 110 NIST 800-171 controls and 320 assessment objectives on the DoD's SPRS v1.2.1 methodology, and a live, read-only Microsoft Graph integration across 11 least-privilege scopes pulls a tenant's own configuration as the evidence behind the technical controls.
- Architected the platform to never store CUI, keeping it outside FedRAMP authorization scope, with SSP and POA&M documentation built from the same assessment data.
- Run Microsoft 365 and Entra environments end to end: identity, Conditional Access, Intune, Exchange Online, tenant migrations, and the Graph and PowerShell automation that removes the manual work around them.
- Build the internal applications and integrations businesses cannot buy off the shelf, connecting finance, payroll, fleet and field systems that were never designed to talk to each other.
- Deliver production systems on an AI-native workflow, Claude Code with spec-driven methodology and MCP tooling, taking projects from architecture to deployment solo at a fraction of conventional timelines.
- Advise founders and owners on architecture, vendor selection, and whether an engineering estimate is honest. Grounded in still writing the code.
Multi-entity construction and field services company.
- Built a unified internal platform that replaced seven paid SaaS services and automated the work running between them: payroll, fleet, safety, expenses and field operations moving without manual intervention.
- Designed and shipped 19 production integrations: Bill.com, QuickBooks Online, Paylocity, SwipeClock, Samsara, Fleetio, KPA Flex, SiteTracker, Vitruvi, Expensify, plus SharePoint and email via the Microsoft Graph API.
- Owned the full Microsoft 365 and Entra ID estate: licensing, Exchange Online, Conditional Access, endpoint management and identity governance.
- Led incident response on a live account compromise: traced sign-in telemetry to an adversary-in-the-middle session token theft, scoped affected accounts, revoked sessions, removed attacker persistence and closed the entry vector. Wrote the runbook afterward.
- Embedded AI agents into operational workflows for document processing, classification and exception routing, reducing manual review across finance and field operations.
Communications and call-handling platform.
- Replaced a $60K/month Twilio dependency with an internal service delivering the same functionality at roughly $400/month. The project paid back its own cost within days.
- Rebuilt the communications layer for reliability and cost predictability at production call volume.
Centralized leasing platform for multi-property operators.
- Built integrations with Yardi, RealPage, ResMan, Twilio and a dozen further property management systems.
- Platform enabled one or two leasing agents to cover fifty properties, the core efficiency thesis of the product.
Managed service provider to REIT clients: Pacific Oak Capital, IQHQ and Sabra Health Care.
- Handled the full IT estate for every client: AWS, Microsoft 365 and Azure, Synology storage, VPN and network administration, end to end, single-handed.
Online ordering and delivery marketplace for restaurants, competing in the category before DoorDash owned it. Acquired.
- Built 15 to 20 POS integrations including Oracle MICROS, NCR Aloha, POSitouch, Digital Dining, Dinerware, Focus POS and PAR Brink.
- Owned restaurant onboarding, integration delivery and QA across the merchant side of the marketplace; worked across driver dispatch, order routing and payment processing.
Migrated 1,000+ customers onto the platform following an acquisition with no loss of service; managed services delivery, hosting infrastructure and development team coordination.
Owned build, QA, support and customer onboarding through an early growth phase; established workflows the team scaled on.