About this episode

Toby Weiss discusses the importance of strategic technology decisions in ministries and shares insights from his experience in the nonprofit sector.

Most ministries don't have a technology problem — they have a strategy problem. Toby Weiss, Co-Founder and CEO of Rooted Software, spent 14 years as the Global CIO of Jews for Jesus before launching a company with one purpose: helping ministries stop patch-working technology together and start wielding it strategically. In this episode, Toby shares what he's learned across hundreds of ministry engagements — and why the hardest part of a CRM rollout has nothing to do with software. Key Takeaways The "hodgepodge" trap is real — and costly. Ministries often solve technology problems one at a time, leading to a patchwork of disconnected systems. Toby explains why reaching a point of strategic maturity — typically around $1–2M in annual revenue — is when organizations need to step back and make deliberate, integrated technology decisions. Outsourced IT is often smarter than in-house. For ministries with fewer than 150 staff, Toby makes a compelling case that outsourced IT delivers broader expertise, greater availability, and lower cost than hiring internally — often cutting IT expenses by 50% or more while actually increasing service levels. Not all CRMs are created equal — and the…

Topics covered

• technology strategy
• ministry engagement
• CRM systems
• outsourced IT
• nonprofit technology

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