- Track 3 – Work Smarter
Why AI Fails at Small Businesses (And How the Winners Get It Right)
About This Session
Abstract
Most small businesses that adopt AI don’t get the results they were promised. The tools usually work fine. The business underneath them often doesn’t.
This panel is about what has to be in place first.
AI accelerates whatever you already have. Where the systems, processes and project management fundamentals are solid, it’s a genuine multiplier. Where they aren’t, it just helps you arrive at the wrong answer faster — and at scale.
Arsh Singh (Digital Marketing Strategist at What Works Marketing and PlusROI Online Marketing) moderates a conversation with operators who have done this work inside real businesses — including the parts that didn’t go to plan.
We’ll dig into the specific fundamentals that determine whether AI works for a business, what implementation actually looks like week to week, and where each of these operators would tell you to start tomorrow.
Speakers
Arsh Singh
What Works Marketing & PlusROI Online Marketing
Arsh Singh is a digital marketing strategist and AI enthusiast. He leverages AI tools to create leverage at the intersection of marketing and data.
Sheila Wynne Fung
AI Implementation Consultant
Sheila Wynne Fung is an AI implementation consultant who starts before the tools do. Her focus is operational truth: where work quietly slows down, where teams have built workarounds, and how the messy realities of a business get baked into standard operating procedure — all of which AI will faithfully accelerate if you don't find...
Ian Slipp
Rubric Marketing
Ian Slipp is the founder of Rubric Marketing and sees this from the smallest end of the scale. He builds purpose-fit tools for an audience of one, and has replaced a large share of his own software subscriptions in the process — a useful counterweight to the idea that AI adoption means buying more.
Owen Mead-Robins
Co-Founder, CEO & CTO, Bluefield Software
Owen Mead-Robins has spent more than twenty years building software and leading engineering teams, split between startups and large companies including Tableau, Salesforce, and Workday. For the last two years he has built two products hands-on with AI: Bluefield, a platform for farmers’ markets and small-town government, and TrellisCharts, a financial planning tool for financial...
Track
- Track 3 – Work Smarter
Date
November 5, 2026
Time
2:30 pm
–
3:15 pm
Room
Saanich Room