IT Strategy Archives - Deliver Digital

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How to Hire a Fractional CIO: Cost, Scope, and Accountability

How to Hire a Fractional CIO: Cost, Scope, and Accountability You have an IT manager who is good at their job and completely out of runway. Every vendor conversation ends with your team taking the vendor's word for it.…

ZachSeptember 16, 2026

Blog delivery IT Strategy Leadership & Strategy Organizational Strategy Technology Partnership transformation

How to Evaluate an IT Managed Service Provider You Already Have

How to Evaluate an AI Investment Before You Approve the Budget You pay your MSP the same amount every month, and every month the systems stay up. Tickets close inside SLA. The report is green. And you still have no…

ZachSeptember 2, 2026

Blog delivery IT Strategy Leadership & Strategy Organizational Strategy

How to Evaluate an AI Investment Before You Approve the Budget

How to Evaluate an AI Investment Before You Approve the Budget Somebody on your leadership team brought up AI again this month. Maybe it was your CEO asking what the plan is. Maybe it was a board member mentioning that…

ZachAugust 19, 2026

Blog delivery IT Strategy Leadership & Strategy Organizational Strategy

Why Good Tech Decisions Still Fail

Why Good Tech Decisions Still Fail The decision was fine. That's the part that stings. You did the work: compared the platforms, pushed back on the pricing, got the leadership team aligned, signed the contract. Eighteen months later, the system…

ZachAugust 12, 2026

Blog delivery IT Strategy Leadership & Strategy Organizational Strategy Technology Partnership

Why Your Digital Transformation ROI Died Before the Project Began

Why Your Digital Transformation ROI Died Before the Project Began The ERP went live eighteen months ago. The CRM migration wrapped last spring. Somewhere in an old board deck there's a slide promising efficiency gains and faster decisions, and somewhere…

ZachJuly 22, 2026

Blog delivery IT Strategy Leadership & Strategy Organizational Strategy Technology Partnership

Why Summer Is the Right Time for a Technology Discovery Sprint

Why Summer Is the Right Time for a Technology Discovery Sprint Your calendar clears out in July. Meetings get shorter, inboxes get quieter, and half your leadership team is somewhere between a cottage and a conference call they'd rather skip.…

ZachJuly 8, 2026

Blog delivery IT Strategy Leadership & Strategy Organizational Strategy Technology Partnership

How to Avoid Buyer’s Regret When You Evaluate Software Vendors

How to Avoid Buyer's Regret When You Evaluate Software Vendors Most teams think they're bad at choosing software. What they're actually bad at is evaluating the people selling it to them. If you've ever sat through a polished demo,…

ZachJune 24, 2026

Blog delivery IT Strategy Organizational Strategy

How to Run a Vendor Selection Process That Actually Ends

How to Run a Vendor Selection Process That Actually Ends Most organizations don't have a vendor selection problem. They have a decision-making problem that vendor selection exposes. The software evaluation has been running for three months. There are five vendors…

ZachMay 27, 2026

IT Strategy8

How to Hire a Fractional CIO: Cost, Scope, and Accountability

How to Evaluate an IT Managed Service Provider You Already Have

How to Evaluate an AI Investment Before You Approve the Budget

Why Good Tech Decisions Still Fail

Why Your Digital Transformation ROI Died Before the Project Began

Why Summer Is the Right Time for a Technology Discovery Sprint

How to Avoid Buyer’s Regret When You Evaluate Software Vendors

How to Run a Vendor Selection Process That Actually Ends

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