Insights
A carefully curated collection of insights, strategies, and writings from the Rudder team—designed to help navigate complex digital challenges with clarity, simplicity, and purpose.
- April 30, 2026
How Nonprofits End Up Locked In by Their Software Vendors
Nonprofit software vendor lock-in turns a routine purchase into a hostage situation three years later. Here is how the trap works, the signs you are already in it, and what to do before the next renewal.
Matthew CristCo-Founder, Chief of Technology - April 24, 2026
ADA Title II Deadline Extended to 2027. Don't Spend the Year Waiting.
The DOJ pushed the ADA Title II web accessibility deadline to 2027 for larger public entities and 2028 for smaller ones. Here's what to do with the extra year, and why doing nothing is the wrong move.
Matthew CristCo-Founder, Chief of Technology - April 21, 2026
Signs It's Time to Replace Your Digital Agency
Most organizations wait too long to switch agencies. Here's how to tell when it's time, and what to do about it without getting stuck.
Matthew CristCo-Founder, Chief of Technology - April 16, 2026
Your Tech Team Doesn't Need More People. It Needs Direction.
Most organizations hire when they hit a technology wall. Six months and $180,000 later, they have more people and the same problems. The gap is almost never headcount.
Matthew CristCo-Founder, Chief of Technology - April 6, 2026
Get an AI Audit Before You Buy Another Tool
Most companies buy AI tools without knowing what they need. An AI systems audit saves you from expensive mistakes and shows you what's actually worth building.
Matthew CristCo-Founder, Chief of Technology - April 6, 2026
The Real Cost of Bad Technology Decisions for Nonprofits and Government
Bad technology decisions cost mission-driven organizations more than money. They cost time, trust, and mission impact. Here's what goes wrong and why it keeps happening.
Matthew CristCo-Founder, Chief of Technology - April 6, 2026
Why Your Nonprofit Needs a Fractional CTO (Not a Full-Time One)
Most nonprofits can't afford a full-time CTO — and don't need one. A fractional CTO gives you senior technology leadership without the $250K salary.
Matthew CristCo-Founder, Chief of Technology - April 5, 2026
What is an AI Systems Audit?
An AI systems audit is a structured assessment of your organization's operations to identify where artificial intelligence can deliver real, measurable improvements — and where it can't.
Matthew CristCo-Founder, Chief of Technology - April 5, 2026
What is a Fractional CTO?
A fractional CTO is a senior technology leader who works with your organization part-time, providing the strategic guidance of a full-time executive without the full-time cost.
Matthew CristCo-Founder, Chief of Technology - April 5, 2026
What is digital accessibility compliance?
Digital accessibility compliance means your website, applications, and digital services can be used by people with disabilities — and that you meet the legal standards requiring it.
Matthew CristCo-Founder, Chief of Technology - October 12, 2025
Drupal Is More Than a CMS: Building Data Platforms and APIs That Power Real Systems
When most people hear "Drupal," they immediately think of content management: articles, pages, blocks, and menus. But what makes Drupal truly powerful isn't just how it manages content. It's how it can also model data, enforce governance, and share that data across systems.
Matthew CristCo-Founder, Chief of Technology - August 9, 2025
Drupal is dying
Not because it is useless. Because the incentives around it push buyers away.
Matthew CristCo-Founder, Chief of Technology - July 14, 2025
How-to host Drupal 11 on Heroku
Heroku doesn't usually come up in conversations about Drupal hosting. Most teams reach for it when building Rails apps, Node backends, or launching SaaS prototypes. But that doesn't mean it's off the table for Drupal.
Matthew CristCo-Founder, Chief of Technology - June 25, 2024
The credibility of complexity
Complexity intensifies as internet development evolves. Remember the early days? A simple website with basic HTML and a few images was enough. But, new tech and higher standards have made it hard to make tools for users.
Matthew CristCo-Founder, Chief of Technology - March 1, 2024
How to properly log an issue
Logging issues on your project is an inevitability. Unfortunately, so are the hassles that come with improperly logged issues.
Matthew CristCo-Founder, Chief of Technology
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