#96 - Saved for Good Works: How Toby Weiss Built a Tech Career in Service of the Kingdom

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 TakeawaysThe "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 wrong fit is expensive. Toby walks through key decision variables:Is the vendor primarily serving nonprofits or faith-based organizations?Do you need an off-the-shelf solution like Virtuous, or a more customizable platform like SiteStacker?Is best-of-breed or all-in-one the right fit for your organization's workflow?Data migrations are harder than they look. With well over 100 migrations completed, Toby explains why moving from one CRM to another isn't a simple export/import — it involves complex field mapping, business process changes, merge/purge logic, and multiple QA cycles. Treating it seriously from the start saves enormous pain.People and process beat technology every time. During a multi-country CRM rollout at Jews for Jesus spanning 11–12 countries, Toby learned that the technology decisions took six months. Getting people across cultures, languages, and compliance requirements (including GDPR) on board? That took 12 years.Calling and business strategy aren't mutually exclusive. Rooted Software was founded with the mission statement "We exist to help followers of Jesus leverage technology effectively." Toby shares how that conviction — rooted in Ephesians 2:10 — shaped every decision from the company's name to who they serve.Ministry can happen on and off the clock. Outside of Rooted, Toby co-founded Hope 680, a nonprofit that goes out twice a month across six cities in the San Francisco Bay Area to share the gospel with the unhoused. His story of a homeless man in London randomly opening a Bible to Luke 12:28 is one you won't want to skip.If your ministry's technology feels more like duct tape than a strategic asset, this conversation is for you. Toby offers a free consultation and brings zero pressure — just real expertise and a genuine heart to serve. Listen to the full episode, then visit rooted.software to schedule time with Toby directly.ResourcesConnect with Toby & Rooted SoftwareEmail: [email protected] & Scheduling: rooted.softwareLinkedIn: https://www.linkedin.com/in/toby-weiss/Hope 680 Ministryhope680.orgBooks MentionedAddiction and the Local Church by Andy Constable & Mez McConnellThe Heart of Addiction by Mark E. ShawThe Five Dysfunctions of a Team by Patrick LencioniOther ResourcesVirtuous CRMSiteStackerThe Addiction ConnectionLaunchAI by Five QFive Q