You know something's off. You just can't prove it yet.
Fractional technology leadership for founders and CEOs who know something is off but can't pinpoint what. Everything gets DoubleChecked.
Leadership
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 SOC2 and ISO. You don't have it. 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 SaaS tools. 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 tech stack. 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 Rocks. Budget-conscious roadmap. No 80-page PDF that collects dust.
Execute
We embed with your team, drive accountability through weekly L10s, and ship results you can measure.
Justin Kane
Nearly 20 years leading technology strategy, cybersecurity, and operations for growth-stage 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 modernization roadmap, and a prioritized plan that ties every technical initiative 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 modernization roadmap, and a prioritized plan that ties every technical initiative 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 MSP 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 MSP is and isn't doing, with a plan to close every gap.
Your MSP 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 MSP 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.
The 2026 Tech Risk Checklist
For Growth-Stage Founders & Boards
Is your technology adding value or compounding risk?
Get our private diagnostic framework used by PE firms to evaluate technical health before an exit. 15 questions that reveal the truth about your stack.
- Identify hidden technical debt before it breaks
- Benchmark your team's velocity against industry leaders
- Audit your cybersecurity posture in 10 minutes
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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.
Learn moreTechnology Strategy & Roadmaps
We assess your current state, identify high-impact moves, and build a roadmap that aligns with your business goals.
Learn moreRisk, Security & Governance
True executive risk management. We help you understand your exposure, meet compliance requirements, and protect your business.
Learn moreOperational Optimization
We streamline your operations, integrate your systems, and make sure your tools actually work for your team instead of against them.
Learn moreMSP Audit & Financial Review
Independent, executive-level auditing of your Managed Service Provider. We verify SLAs, security, and billing accuracy.
Learn moreExecutive 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.
Learn moreTraction requires discipline, not just good code.
We run our engagements using Entrepreneurial Operating System (EOS) principles. We act as an Integrator for your technology function, ensuring every technical decision maps directly back to your 1-year plan and 10-year target.
L10 Meeting Rhythm
We embed into your weekly leadership cadence, reporting on technical KPIs (Scorecard) and solving root-cause issues (IDS) instead of treating symptoms.
Accountability Chart
We establish clear ownership for every system, vendor, and process. No more ambiguity about who is responsible when technology breaks.
Rocks & Vision
Technology roadmaps are broken down into 90-day “Rocks” that directly support your broader V/TO (Vision/Traction Organizer).
Recent Success Stories
Real outcomes for growth-stage 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: $350K+/year. DoubleChecked: a fraction of that, with no long-term contract.
Frequently Asked Questions
Straight answers for executives evaluating fractional leadership.