At TechSoup Connect Canada’s April 1 event, we were treated to a deep dive into the practical side of AI and automation with Chaplain Timothy “TIG” Heaslet. Far from a buzzword-laden keynote, this was a grounded, generous session filled with real-world use cases, thoughtful caution, and a whole lot of heart.
TIG, a nonprofit leader and tech educator, brought both wisdom and warmth as he guided participants through how AI-powered automation can help organizations do more with less.
Who Is Chaplain Timothy “TIG” Heaslet?
Chaplain Timothy “TIG” Heaslet isn’t your average tech speaker. His path to nonprofit technology began through a mission to love and empower youth, especially those impacted by the loss of military or first responder parents. His work spans organizations like America’s Children of Fallen Heroes and his latest initiative, MissingPixel.org, which provides underserved youth with tech training, mentorship, and personal development.
Highlights from the Session
Start With Strategy, Not Shiny Tools
Before jumping into AI, TIG emphasized the need to revisit your nonprofit’s goals and workflows. AI can’t fix what isn’t clearly defined. Instead, it’s most powerful when it’s applied to well-understood processes—especially repetitive or data-driven ones.
Understanding Automation: Procedural vs. Agentic
TIG broke down two key automation types:
- Procedural automation: Traditional, rules-based systems (think Zapier or Make.com) that follow predictable steps.
- Agentic automation: Powered by large language models (LLMs) like ChatGPT or Claude, these workflows bring a conversational or decision-making layer into the mix.
While agentic automation opens new doors (like custom chatbots or proposal writers), it’s not without challenges. TIG cautioned about relying too heavily on agentic flows due to inconsistency and potential errors—especially when data accuracy is critical.
Real-World Nonprofit Use Cases
Some practical AI-powered automation examples TIG shared:
- Automatically texting contacts for updated mailing addresses and syncing that info into your CRM
- Building chatbots that escalate complex queries to humans, then learn from the answers
- Using vector databases (like Pinecone or Supabase) to create a searchable knowledge base from internal PDFs or video transcripts
- Testing multiple LLMs via tools like OpenRouter to find the best fit for your content type
Security and Privacy Considerations
For organizations handling sensitive data (like youth programs or legal aid), TIG stressed the importance of self-hosting or choosing tools that meet compliance standards. He recommended open-source options like n8n or Activepieces for building secure, customizable workflows.
The Takeaway: Build Slow and Smart
The nonprofit AI landscape is evolving fast. But TIG’s message was clear: don’t get distracted by hype. Start with simple use cases. Focus on processes you already understand. Build with intention—and always, always test for failure points before scaling.
As TIG put it, “This is the worst this tech is ever going to be. It only gets better from here.”
Want to Learn More?
TIG is open to connecting with other nonprofit folks looking to explore AI and automation. You can find him on LinkedIn or email tig@quietlyworking.org
And stay tuned—TechSoup Connect Canada may just bring TIG back for another session later this year. With the pace of change in AI, three months might as well be a lifetime.