You know something's off. You just can't prove it yet.
Most companies don't need a full-time CTO. They need one on their side.
DoubleChecked provides fractional CTO advisory and independent MSP oversight to founders and CEOs who are done making expensive technology decisions without anyone in their corner.
Sound familiar?
These are the problems that keep executives up at night. We fix them.
The IT Black Box
Costs keep climbing. Systems keep breaking. Nobody can explain why.
Compliance Kills Deals
Enterprise buyers want security certifications (SOC2, ISO). You don't have them. Revenue stalls.
IT Leadership Gap
Your IT team plays helpdesk. You can't challenge them because you don't speak their language.
Fragmented Systems
Dozens of software subscriptions. None of them talk to each other. Your team wastes hours on workarounds.
Built for companies like yours
You have 10 to 200 employees. Technology touches everything in your business but nobody at the leadership table owns it. You know something is wrong, you just can't prove it yet.
How you take back control
Four phases. No fluff. Every engagement follows this playbook.
Discover
We interview leadership, review contracts, and audit your systems and vendors. No assumptions. Just facts.
Diagnose
We map every gap, risk, and cost leak. You get a clear picture of where you stand and what's costing you.
Plan
Prioritized 90-day goals. Budget-conscious roadmap. No 80-page PDF that collects dust.
Execute
We embed with your team, drive accountability through weekly leadership meetings, and ship results you can measure.
Justin Kane
Nearly 20 years leading technology strategy, cybersecurity, and operations for growing companies. Certified EOS Integrator. Small Business Leader of the Year. Jax IT Council Board Member. He built DoubleChecked for one reason: business owners deserve someone in their corner who actually understands the stakes.
Full backgroundWhat changes when you DoubleCheck
The gap between “winging it” and having a senior technology leader in the room.
Your CEO is the de facto CTO. Board meetings lack technical clarity and major decisions get made on gut feel.
A fractional executive owns the technology narrative, delivers board-ready reporting, and brings structure to every critical decision.
Your CEO is the de facto CTO. Board meetings lack technical clarity and major decisions get made on gut feel.
A fractional executive owns the technology narrative, delivers board-ready reporting, and brings structure to every critical decision.
Your platform was built for where you were three years ago. Every new feature takes twice as long and nobody agrees on the roadmap.
A current-state assessment, a clear plan to update what's outdated, and a prioritized roadmap that ties every investment to a business outcome.
Your platform was built for where you were three years ago. Every new feature takes twice as long and nobody agrees on the roadmap.
A current-state assessment, a clear plan to update what's outdated, and a prioritized roadmap that ties every investment to a business outcome.
A prospect asks for your SOC2 report. You stall, lose the deal, and scramble to figure out where to even start.
Compliance roadmap in place. Audit-ready documentation. You walk into the next enterprise deal with confidence.
A prospect asks for your SOC2 report. You stall, lose the deal, and scramble to figure out where to even start.
Compliance roadmap in place. Audit-ready documentation. You walk into the next enterprise deal with confidence.
Your team runs on a patchwork of disconnected tools. Critical updates live in Slack threads. Nobody has a single view of what's happening.
Integrated systems, automated workflows, and a weekly scorecard your leadership team actually reads and acts on.
Your team runs on a patchwork of disconnected tools. Critical updates live in Slack threads. Nobody has a single view of what's happening.
Integrated systems, automated workflows, and a weekly scorecard your leadership team actually reads and acts on.
Your outsourced IT provider says 'everything is fine.' You have no way to verify if backups run, patches are current, or if you're being overbilled.
An independent audit that confirms (or exposes) exactly what your IT provider is and isn't doing, with a plan to close every gap.
Your outsourced IT provider says 'everything is fine.' You have no way to verify if backups run, patches are current, or if you're being overbilled.
An independent audit that confirms (or exposes) exactly what your IT provider is and isn't doing, with a plan to close every gap.
You've been searching for a CTO for six months. Recruiters keep sending candidates who can't hold a technical conversation past the resume.
A CTO-led search that evaluates candidates on architecture thinking, team leadership, and cultural fit. Not just keyword matching.
You've been searching for a CTO for six months. Recruiters keep sending candidates who can't hold a technical conversation past the resume.
A CTO-led search that evaluates candidates on architecture thinking, team leadership, and cultural fit. Not just keyword matching.
MSP Contract Red Flags
12 Things Your IT Company Hopes You Never Read
Your MSP contract was written to protect them, not you.
Most business owners sign MSP contracts without knowing what they actually say. This guide covers the 12 most common clauses that cost you money, limit your options, and put your business at risk.
- Auto-renewal traps and exit fees that lock you in
- SLA language that sounds good but has no teeth
- Liability caps, subcontracting rights, and audit restrictions
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Core Advisory Services
Strategic leadership, not just support tickets.
Fractional Executive Leadership
Senior oversight for your technology function without the full-time hire. We sit on your leadership team and drive accountability.
View detailsTechnology Strategy & Roadmaps
We assess your current state, identify high-impact moves, and build a roadmap that aligns with your business goals.
View detailsRisk, Security & Governance
True executive risk management. We help you understand your exposure, meet compliance requirements, and protect your business.
View detailsOperational Optimization
We simplify your operations, integrate your systems, and make sure your tools actually work for your team instead of against them.
View detailsMSP Advisory
Independent MSP contract reviews, vendor selection advisory, and managed services audits. Fixed-price engagements designed to put a CTO in your corner before you sign, switch, or renew.
See MSP Advisory ServicesExecutive Search & Placement
Don't hire a technical leader on gut feeling. Our CTO-led search ensures every candidate is DoubleChecked for skills and cultural fit.
View detailsLooking for dedicated IT strategy leadership? Explore our Virtual CIO (vCIO) services or get an independent MSP Advisory services.
Do you run on EOS?
If your company uses the Entrepreneurial Operating System, you already know the value of structure, accountability, and 90-day execution cycles. DoubleChecked brings that same discipline to your technology function. Justin is a Certified EOS Integrator™ who speaks your language and fits into your existing rhythm.
See how we work with EOS companiesRecent Success Stories
Real outcomes for growing companies.
"We Outgrew Our IT Guy"
A 60-person professional services firm had relied on the same one-man IT shop for years. The owner knew something was off but couldn't articulate what "good" looked like. Systems were slow, nobody trusted the backups, and every new hire took a week to get set up. When they finally asked for a technology roadmap, their IT provider couldn't produce one.
We ran a full assessment of their environment, found six figures in wasted spend across unused licenses and overlapping tools, and built a 12-month roadmap the leadership team could actually understand. Within 90 days they had reliable backups, same-day onboarding, and a vendor who could answer their questions in plain English.
Compliance Audit, Zero Preparation
A regional healthcare company landed a contract with a major hospital system, then learned the deal required a formal security compliance audit. They had no documented policies, no access controls worth showing an auditor, and no idea what was even on their network. The CEO described it as "finding out you need to pass a test you didn't know existed."
We built their entire compliance program from the ground up: asset inventory, access policies, risk assessments, and the documentation to prove it all. They passed the audit on the first attempt, closed the hospital contract, and now use that compliance posture as a competitive advantage in every new proposal.
Five Locations, Five Different Setups
A multi-location services company had grown through acquisition and every office was running something different. Different email systems, different file storage, different ways of tracking clients. The owner couldn't pull a single report across the business without calling five managers. Employees transferring between offices had to learn entirely new systems.
We standardized everything onto a single platform without shutting down any location during the transition. The owner now gets one dashboard for the whole company. Employee transfers are painless, client data follows them, and the company cut their combined technology spend by 30% by eliminating four redundant systems.
How Engagements Start
Most clients begin with a diagnostic. No long-term commitment required to get started.
Focused Diagnostic
We assess your current technology environment, identify blind spots, and deliver a clear picture of where you stand. No jargon, no fluff. You walk away with actionable findings whether or not we work together.
Right-Sized Engagement
Based on what the diagnostic reveals, we build an engagement that fits your situation. Fractional leadership, a defined project, or ongoing advisory. You pick the model that makes sense for your business and budget.
Ongoing Partnership
As your fractional CTO/CIO/CISO, we integrate with your leadership team and run on 90-day cycles aligned to your business goals. Clear deliverables, regular check-ins, and full accountability every quarter.
Not sure where you stand? Start with the diagnostic. It pays for itself.
Full-time CTO: $200K-$350K+/year. Fractional from $2,500/month. No long-term contract.
Frequently Asked Questions
Straight answers for executives evaluating fractional leadership.
Managed service providers and IT consulting firms sell execution: helpdesk support, managed infrastructure, project delivery. DoubleChecked provides strategic leadership. We don't manage your helpdesk or sell hardware. We sit on your side of the table, hold your existing IT providers accountable, and make sure your technology investments are aligned to your business goals. When your MSP evaluates your IT environment, they're grading their own work. We're independent.