DoubleChecked

Industry: Information Technology

Business Size: 1-4

Phone: 9047010153

Address:
1001 Mayport Road, #331206
Jacksonville, FL 32233

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About DoubleCheckedDoubleChecked is a Jacksonville-based fractional CTO and technology advisory firm. We work with founders and business owners who need senior-level technology leadership without a full-time hire, and with companies that want an independent review of their managed IT contracts, vendors, or overall technology strategy. Our job is to translate between the business world and the IT world, in plain language.

What differentiates you from the competition?I've sat on the IT provider side of the table. I know how contracts are structured, where margins are buried, and how decisions get influenced. Owners finally have someone who understands both worlds.

What are your top selling services or products that your company offers?The Fractional CTO engagement runs on 90-day priorities, so there's always a clear answer to what we're working on and why. It's executive-level strategy in plain language, not IT support.

If you had one message to get across to future customers, what would it be?Your IT provider is not your technology strategist. Those are two different jobs. Get an independent voice at the table before you sign the next contract or make the next technology decision.

What is the biggest marketing challenge that you will face in the upcoming year?Most owners don't know they need independent technology advisory until they've already felt the pain. Building awareness around a problem people haven't named yet is the real challenge.

What technologies are having the biggest impact on IT right now? AI is compressing timelines on everything. Security tooling, automation, and cloud management are all being reshaped faster than most IT teams can absorb. The bigger issue is that most SMBs aren’t getting honest guidance on what actually applies to their business versus what’s being oversold.

How do you ensure cybersecurity and data protection across systems? Every engagement starts with understanding what data the business holds and who has access to it. From there we build the right layered approach, whether that’s tightening existing controls, replacing underperforming tools, or filling gaps the current provider missed. Security isn’t a product, it’s a posture. We assess the full environment, identify where exposure lives, and make sure the right controls, contracts, and accountability are in place. Then we verify it’s actually working.

What trends are driving digital transformation? AI adoption, cloud consolidation, and pressure to do more with leaner teams. The challenge for most SMBs isn’t awareness of the trends, it’s having someone help them figure out which ones actually matter for their size and stage.

How are you managing cloud infrastructure and scalability? Every cloud environment should map to a business outcome. We make sure clients understand what they have, what it costs, and whether it’s built to grow with them, then course correct where it isn’t.

What are the key skills in demand for IT professionals today? Communication is underrated. The most valuable IT professionals right now are the ones who can translate technical decisions into business language. That gap between IT and leadership is where most companies lose time and money.

How do you stay current in such a rapidly evolving field? I stay active in the IT industry through board involvement with IT Council and close relationships with providers and peers. Staying fluent in both the business leadership world and the IT world is the whole job.

What’s your approach to innovation and problem-solving in IT? Start with the business problem, not the technology. Most IT decisions go sideways because the technology conversation happens before the business conversation. I work backwards from what the owner is actually trying to accomplish.

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