Leadership Insights

A CEO reviewing a list of ways to get senior tech leadership Without adding a full-time CTO

7 ways mid-market CEOs can get senior tech leadership without Adding a full-time CTO

You probably feel the squeeze. Your board wants real answers on AI, cyber risk, and system reliability, but a $300k-plus full-time CTO still feels like a stretch. You are not alone. Many mid-market firms have serious customers, regulators, and investors, yet rely on an overworked IT lead or a heroic engineer to play “part-time executive.”

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A team working with a ransomware tabletop facilitator for legal services organizations

Ransomware Tabletop Facilitator for Legal Services Organizations (Incident Ready Decision Gates)

It’s 9:12 a.m. Intake is stacking up, advocates can’t open case files due to the ransomware attack, and the phones won’t stop. Someone forwards a screenshot: a ransom note. The panic doesn’t come from the tech details. It comes from the cyber threat landscape, what your team protects, client safety, confidentiality, and the ability to

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A team reviewing a justice organization technology roadmap

Justice Organization Technology Roadmap: A Board-Ready 90-Day Plan

Your intake queue is growing. Partner handoffs are failing. A funder report is due, and the numbers don’t match what staff know is true. These issues widen the justice gap in service delivery. That’s how tech debt shows when there is no justice organization technology roadmap in place. Not as an “IT problem,” but as

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A Mission-Focused Software Licensing Strategy for Nonprofits

A smart software licensing strategy for nonprofits can be the difference between software being a chaotic, unpredictable expense and it becoming a true strategic asset. It's about moving from reactive, ad-hoc purchases to a disciplined approach that aligns every tool with your mission. This is how you transform a fragile, patched-together system into a reliable

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An image of a team performing nonprofit systems map workshop

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

Three Questions PE Firms Should Ask About Portfolio Company Technology

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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A team developing a nonprofit cybersecurity plan

Building A Nonprofit Cybersecurity Plan: A Practical 90-Day Launch Program

If you lead a mission-driven nonprofit, you already know this truth: trust is part of the service. Clients share details they may not even tell family. Donors trust you with payment data and private intent. Staff store case notes, benefits documents, safety plans, and court records while juggling too much work. A cyber incident doesn’t

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A team learning about offboarding for self help services organizations

Access Control and Offboarding for Self Help Services Organizations (Secure Forms and Portals Without Friction)

Court self-help programs, navigator teams, and legal aid style nonprofits run on motion. Part-time staff. Pro bono partners rotating in and out. Interns who start strong, then disappear when school ramps up. Vendors who “just need access for a minute.” All of it under urgent deadlines that demand effective employee offboarding. The core security risk

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