Rethinkit serves as your fractional IT director and help desk — covering everything from Microsoft 365 and cybersecurity to networking and compliance. Real people. No ticketing. No hold times.
Rethinkit leverages AI across everything we do — faster diagnostics, smarter documentation, proactive monitoring, and better outcomes for your team.
Rethinkit handles the full stack of corporate technology — so you can focus on your business, not your IT.
Your dotted-line CTO. We advise on vendor selection, technology strategy, and infrastructure decisions — without the cost of a full-time hire.
Real people answer your calls. M–F 9–6 with instant access, on-call weekends. Under 15 minutes? Never billed. We want you to call.
Full management of your cloud identity, email, OneDrive, SharePoint, and Teams. Monthly usage reports, MFA enforcement, and user lifecycle.
CrowdStrike, Microsoft Defender, Intune endpoint management, phish testing with KnowBe4, email filtering, DKIM/DMARC, and more.
Cloud-managed UniFi networking for your office. Wi-Fi, routing, monitoring, and outage alerting — all centrally managed by Rethinkit.
We build your IT operations manual, employee guides, and onboarding/offboarding checklists. Your data — not ours — yours to keep forever.
Most MSPs route you through layers of tiers and ticketing systems. We don't. Your call is answered by someone who knows your company, your setup, and your people.
No ticket numbers, no hold queues, no "first-level tech" delays. You reach someone who knows you.
We believe in earning your business every month. No multi-year contracts — just a 90-day cancellation notice after the first 6 months.
We don't just fix the instance. We find the underlying problem and fix that too, so you don't call us again for the same issue.
Microsoft, Adobe, Zoom — passed through at cost. We charge a small management fee, never a markup.
Rethinkit was built by two technologists who believed small and mid-size businesses deserved the same caliber of IT support as the largest firms — without the overhead or the runaround.
Jason has spent over two decades at the intersection of technology and business strategy. Before founding Rethinkit, he held senior IT leadership roles serving financial services and professional services firms across New York. An early advocate for enterprise AI, Jason was one of the first practitioners in the managed IT space to integrate AI tooling into day-to-day operations — from automated diagnostics and intelligent documentation to proactive monitoring and client communications. He brings both the technical depth and strategic perspective that Rethinkit clients rely on.
Charles brings deep hands-on expertise across enterprise infrastructure, cloud platforms, and cybersecurity. His background spans network engineering, Microsoft 365 administration, endpoint management, and compliance-driven IT deployments for regulated industries including financial services and healthcare. Charles is the architect behind Rethinkit's technology platform — designing the systems and processes that allow the team to deliver consistent, high-quality support at scale without sacrificing the personal touch that defines the Rethinkit experience.
Financial services, healthcare, and other compliance-heavy firms trust Rethinkit to handle the technology requirements that auditors care about.
FINRA-compliant archiving via Global Relay or Smarsh. Captures the full inbound/outbound stream. Management-searchable across all history.
Documented proof your firm takes cybersecurity seriously. Three tiers: awareness training, cyber review, and full penetration testing.
We draft your cybersecurity and information security policies, handle chain-of-command access controls, and produce audit-ready reports.
Rethinkit assists with third-party technology assessments, investor attestations, and regulatory compliance questionnaires.
From first call to fully onboarded, here's how Rethinkit gets to work.
We learn your business, your team, and your current technology. No commitment, no pressure — just a conversation.
We scope a Technology Platform tailored to your size, industry, and compliance requirements with transparent pricing.
We take ownership of your IT infrastructure, document everything, set up monitoring, and train your help desk on your team.
Monthly reports, proactive alerts, help desk access, and a Rethinkit partner advocating for your IT — every month.
Use the options below to connect with a Rethinkit technician now, or install background access so we can assist you anytime without interrupting your workflow.
One-time remote session. A technician connects to your computer right now to resolve your issue.
Start Session →Install continuous background access on your Windows PC so our team can help you anytime, without interruption.
Download .msi →Install continuous background access on your Mac so our team can help you anytime, without interruption.
Download .pkg →No obligations, no canned demo. Just a straight conversation about where your technology is today and where it should be.