Leadership Insights

Tech and business teams sync up for better results

8 ways tech and business teams sync up for better results

When you sit in a board meeting and the conversation turns to technology, what does “good” actually look like? For many mid-market CEOs and COOs, tech feels expensive, risky, and oddly detached from the real work of winning customers and protecting margins. Projects stall, vendors confuse the story, and no one is fully sure if […]

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An image of a team of people who are learning how to audit their tech stack without starting a civil war in their company

How To Audit Your Tech Stack Without Starting A Civil War In Your Company

Nobody wakes up excited for an audit, least of all your IT team. For many leaders, the idea of touching the tech stack feels like kicking a hornet’s nest of vendors, opinions, and sunk cost. Yet doing nothing is already a choice. You feel it in missed revenue, rising SaaS bills, outages, and board questions

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A team discussing 7 real-world technology roadmap examples from mid-market Companies

7 Real-World Technology Roadmap Examples From Mid-Market Companies

You are not short on ideas. You are short on a clear, believable technology plan that your team can actually execute. If you are a growth-minded CEO or founder, you probably ask yourself a simple question: What does a good, practical technology roadmap look like for a company like mine? Not a glossy vendor slide.

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A CEO wondering what questions every CEO should ask about their technology roadmap

19 Questions Every CEO Should Ask About Their Technology Roadmap Before The Next Budget Hits

Most CEOs will sign off on millions in technology spend this year without feeling truly confident in what they just approved. The charts look polished. The buzzwords sound familiar. But the real questions stay unasked. If you feel like your technology roadmap is written in a foreign language, you are not alone. You care about

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A team surrounding an Interim CTO for Legal Services Organizations

Interim CTO for Legal Services Organizations: A Practical Guide to Modernization

It’s the end of the grant cycle, and a familiar panic is setting in. Key program data is siloed across three different spreadsheets and a case management system that refuses to sync. Your small team is completely burned out from weeks of manual data entry, just trying to pull together a coherent report for a

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