strategic IT planning - Free Resources From CTO Input

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The Nonprofit Systems Map Workshop, How to Document Your Real Workflows in 2 Workshops

The intake queue is exploding. A partner handoff failed again. A funder report is due Friday, and the numbers don’t reconcile with last quarter’s spreadsheet. When that happens, it’s tempting to hunt for a new tool. But the tool isn’t the work. The work is the flow of decisions, handoffs, approvals, and sensitive information that […]

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Three Questions PE Firms Should Ask About Portfolio Company Technology

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You are sitting in a portfolio review, flipping through the deck. The deal thesis is clear, the market story holds, the numbers look fine. Then you hit the “IT” slide. One box, three bullets, and a big budget number you do not fully trust. That is the problem behind Three Questions PE Firms Should Ask

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Executive Coaching on Digital Strategy Legal: A Quiet Power Tool for Justice Leaders

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The work you lead is already heavy. Case backlogs. Emergency grants. New reporting rules every year. Now AI tools, cloud systems, and cyber risks sit on top of it all. For legal nonprofits, executive coaching on digital strategy legal is no longer a nice-to-have. It is focused support that helps legal executives, such as the

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Justice Organization Technology Roadmap: A Calm Path From Chaos To Clarity

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If you run a justice-focused nonprofit, your tech probably feels like a pile of Jenga blocks. Old systems needing legacy system modernization. New tools. Manual work everywhere. A justice organization technology roadmap is a simple way to turn that pile into a plan through smart technology investment prioritization. It is a 1 to 3 year

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3 Questions CEOs Must Ask About Security Investments To Protect Growth

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If you feel unsure whether your security budget is too high, too low, or simply misdirected, you are not alone. Most growth-minded CEOs and founders feel the same tension. You sign off on six-figure renewals, sit through vendor pitches, then still worry about the next ransomware headline. Boards, lenders, and large customers now expect clear

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From Spreadsheet Chaos to Clarity: Reducing Spreadsheet Overload in Legal Aid

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Legal teams did what they had to do. Intake logs in Excel. Clinic rosters in Google Sheets. Grant reports in a dozen different files, each with its own tabs, color codes, and macros that only one person understands. Over time, those quick fixes turn into a shadow system. Dozens of trackers live in different folders

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Cloud Costs Are Out Of Control: How To Control Cloud Costs

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You are a growth-focused CEO or founder. Your cloud spending has quietly doubled in the last 12 to 18 months, yet revenue has not. You see the invoices, but you do not see the story. Cloud was sold as flexible and a source of cost efficiency. Now it feels unpredictable, hard to budget, and even

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Real-World Best Practices for Working With Fractional Leaders

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You are a CEO or COO who keeps writing bigger checks for tech and security and getting weaker returns. Projects slip, cyber risk feels fuzzy, and the board is asking pointed questions you cannot answer in one slide. The tension is clear: rising spend, flat impact, and growing exposure. A fractional CTO or CISO gives

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Aligning Technology Projects With Strategy For PayOff

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You are a CEO, COO, or founder who is trying to leverage technology and getting less back. Projects slip. Systems do not connect. Vendors push shiny tools that do not align with your digital strategy or fix core problems. Your board keeps asking how IT spend supports the IT strategy, and you do not have

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An image of a team facing a project that is stalled in AI pilot purgatory and how they break out.

Why Your Project Is Stalled In AI Pilot Purgatory (And How To Break Out)

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You are a growth-minded CEO or founder who has said yes to one, two, maybe three AI pilots. The demos looked sharp. The vendor decks were glossy. Your team was excited. Yet your EBITDA has not moved. The executive leadership is asking what your AI strategy is, and you do not have a clean answer.

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