Available · Q3 2026
— Independent IT advisory · Est. 2026

Enterprise technology,
engineered for operational agility.

I partner with CIOs and their teams to modernize endpoint ecosystems, migrate to the cloud, and harden security — without stalling the business.

Matthew Rakoski
Fig. 1
M. Rakoski, Available worldwide · Remote-first.
§ 01 · About

The unglamorous infrastructure that decides whether a business can move.

I have spent my career at the intersection of strategy and operations — the place where a board-level mandate meets the reality of 200,000 endpoints, twelve regulatory regimes, and a change window that closes Friday at 6 PM.

My work focuses on the unglamorous infrastructure that decides whether a business can move: endpoint fleets, identity, digital workplace, and the security posture underneath. Done well, it disappears. Done poorly, it is the ceiling on everything else.

I work independently with a short list of organizations per year. Engagements run from six-week assessments to embedded advisory through a full transformation.

20+
Years in enterprise IT
3
Fortune 500 tenures
200K+
Endpoints under stewardship
$40M+
Documented cost takeout
§ 02 · Services

Four practice areas. Delivered as assessments, advisory, or embedded leadership.

01

Endpoint Modernization

Assessment, roadmap, and execution of endpoint fleet transformations — from Windows, macOS and mobile device strategy through zero-touch provisioning, MDM/UEM consolidation, and lifecycle cost optimization.

  • Fleet audit & TCO baseline
  • Target-state architecture
  • Migration playbooks
  • Vendor rationalization
02

Digital Workplace Strategy

Redesign the employee technology experience end-to-end. Identity, collaboration, virtualization, and the service model behind them — built so IT is an enabler instead of a queue.

  • Persona-based service design
  • VDI / DaaS evaluations
  • Collaboration platform strategy
  • Service desk transformation
03

Cloud & Infrastructure Migration

Pragmatic migration planning for mixed estates. I work with engineering teams on sequencing, risk containment, and the organizational change that turns a lift-and-shift into real modernization.

  • Migration wave planning
  • Landing zone review
  • Run-cost modeling
  • Executive reporting cadence
04

Security Posture & Governance

Translate security controls into operations that actually hold. Endpoint hardening, privileged access, patch discipline, and the reporting that keeps regulators, auditors, and the board aligned.

  • Control maturity review
  • Zero-trust endpoint roadmap
  • Patch & vulnerability ops
  • Board-ready reporting
§ 03 · Experience

A career built in the machine rooms of the Fortune 500.

Oracle
2022 — 2026
Atlanta, GA
Senior Director, Endpoint Engineering
  • Oversee high-performing teams across security, architecture, and operations supporting 200,000+ endpoints spanning Windows, macOS, virtual desktops, and print services.
  • Lead 5 teams and 60+ direct-hierarchy resources designing, developing, testing, and maintaining the security and productivity platforms core to Oracle's $57B annual revenue.
  • Developed and implemented AI guardrails and security controls to protect mission-critical corporate data across a highly distributed workforce.
Truist Bank
2016 — 2022
Atlanta, GA
Group Vice President, Endpoint Engineering & Operations
  • Led engineering and operational support for 43,000+ endpoint devices across the SunTrust enterprise, maintaining system reliability and performance at bank scale.
  • Headed development of the infrastructure platforms enabling enterprise-wide Microsoft 365 migration — Teams, Exchange, SharePoint, OneDrive, Skype, and Azure AD — maximizing collaboration and cloud integration.
  • Implemented Desktop Analytics across all endpoints, augmenting telemetry and enabling proactive system diagnostics.
  • Administered vBlock infrastructure supporting 13,000+ VDI users across branches, call centers, and contractor networks for scalable, secure access.
The Coca-Cola Company
1998 — 2015
Atlanta, GA
Director, Client Strategy / Engineering
  • Developed and executed multi-year strategic roadmaps for enterprise productivity technologies, driving continuous improvement and adoption of modern platforms.
  • Formulated and launched the enterprise mobile strategy, introducing BYOD policy to support workforce flexibility and reduce hardware expenditures.
  • Spearheaded company-wide Knowledge Sharing initiatives under CIO and CAO sponsorship, fostering collaboration and enterprise learning.
Earlier
Pre-1998
Systems & Infrastructure roles
  • Hands-on operations and engineering across retail, logistics, and managed services.
§ 04 · Principles

How I work.

— 01

Operations first

A strategy that can't be run on Monday is not a strategy. Every recommendation ships with an ops model.

— 02

Measure the takeout

Transformations earn their budget with documented run-cost, risk, and productivity deltas — not slideware.

— 03

Change the fewest things

Modernization is not novelty. The best move is usually the smallest one that unlocks the rest.

— 04

Stay close to the fleet

Decisions made far from the endpoint usually break at the endpoint. I stay close.

§ 05 · Contact

If the ceiling is your infrastructure, let's talk.

I take on a small number of engagements each year. A 30-minute conversation is the best way to see if there's a fit.

LinkedIn
linkedin.com/in/rakoski
Location
Available worldwide · Remote-first
Typical reply within one business day.