Matthew C.Private profile: Upwork shows its earnings only to signed-in members, so we check it every few weeks, not daily. MRR here is a rough estimate (Upwork's six-month earnings ÷ months active). Last read Nov 7, 2026.

I help companies untangle complex IT environments, stalled projects, security problems, migrations, and operational issues with no obvious owner. I tend to get involved when problems cross boundaries. The security issue is also an infrastructure issue. The migration depends on a vendor nobody is managing. The project plan does not match technical reality. Important systems are undocumented. Leadership is getting conflicting answers. Everyone owns a piece of the problem, but nobody owns the whole thing. That is where I work best. I determine the real state of the environment, identify dependencies and root causes, separate urgent problems from noise, and turn ambiguity into an executable plan. My background spans hands-on IT, cybersecurity, MSP operations, infrastructure, software/product development, service delivery, and technical leadership. I spent more than a decade at Dell SecureWorks leading global security initiatives and complex client work. I have also worked with numerous MSPs and mid-market organizations across security, infrastructure, migrations, project execution, and operations. I have also built and operated multiple businesses, including an MSP and software company, and have hired or worked with hundreds of freelancers, consultants, engineers, agencies, and vendors. I understand the difference between completing a technical task and actually improving the system around it. Common engagements include: • IT environment and infrastructure assessments • Cybersecurity posture reviews • Microsoft 365 and infrastructure cleanup • Migration planning, governance, and execution • MSP service delivery improvement • Vendor and project coordination • vCIO / CTO-style advisory • Post-incident and root-cause reviews • Documentation and operational handoff • Security policy and process improvement • Technical due diligence My strength is not knowing one particular product better than everyone else. It is understanding how the pieces fit together. I work across security, infrastructure, applications, vendors, operations, projects, and business requirements rather than treating each as an isolated problem. That lets me recognize patterns quickly, identify where a problem actually originates, and understand the downstream effects of technical decisions. I can usually become productive quickly in unfamiliar environments. The products may change, but the underlying architectures, dependencies, control models, failure modes, and operational patterns are often analogous. My rate reflects senior judgment rather than hours spent reaching an answer. Engagements may be hourly, fixed-price, or structured differently depending on scope and duration. The value is faster diagnosis, better sequencing, fewer false starts, clearer decisions, lower operational risk, and less technical debt. Cheap hours and low total cost are not the same thing. I do not believe in becoming the permanent hero holding a broken environment together. I can step into chaos, but the goal is to leave behind clear ownership, documented systems, sensible controls, and an operation that depends less on individual heroics than it did when I arrived. I communicate early, define scope clearly, document what matters, distinguish facts from assumptions, surface problems rather than hide them, and focus effort where it changes the outcome. If you have a complex IT or security problem, a migration that needs adult supervision, an environment nobody completely understands, or a project where technical and business realities have stopped lining up, we will probably work well together. Tools and platforms I work with regularly: AFI Airtable Aruba Asana Autotask Avanan Azure Barracuda BitDefender BitTitan Box BreachSecureNow Calendly CheckPoint Cisco Security Citrix CloudAlly Cloudflare ConnectWise Confluence Crowdstrike DataDog Dell DMarcly DNSFilter Docker Dropbox Duo Datto Fortinet Google Cloud Google Workspace GoDaddy GitHub Gurucul Halo Hyper-V InTune Involv IT Glue JIRA Juniper Kaseya Keeper KnowBe4 LastLine LastPass Lenovo Load Balancers METRC Meraki MigrationWiz Mimecast Microsoft Defender Monday MoveBot Ninja RMM N-Able Ninety N8N NoCoDB Okta Panda Pantheon PagerDuty Palo Alto Pillr Product Board Push Security Qualys Remedy Rocket Cyber Salesforce SecureWorks SendGrid SentinelOne ShareGate SharePoint SiteGround Snort Sonicwall Sourcefire Splunk StackPath Sucuri Teams TeamWork ThreatLocker Trend Micro Umbrella Ubiquiti Webroot WebTitan WPEngine WordPress Zapier Zoom