From "At Risk" to "At The Ready"

Jeremy Ryan
Aug 10
3 min read

Discover how small businesses can outpace big players with focused AI strategy. Avoid pilot purgatory and unlock wins now. Watch & learn.

AI isn’t just about the latest tool or hype cycle—it’s about strategy. In this episode of Polarity: AI for Small Business, Jeremy and Jim break down how AI is disrupting jobs, transforming industries, and reshaping business strategy. From Microsoft’s job risk report to Trunk Tools’ AI for construction, the big lesson is clear: SMBs that start small, focus, and align AI with business goals will come out ahead.

If you’re a small business leader overwhelmed by choices, this roadmap will help you skip “pilot purgatory” and build momentum with early AI wins.

Key Takeaways

Microsoft’s AI research shows clerical jobs are most at risk, while trades like electricians remain safer (for now).
Trunk Tools shows how niche AI agents can reshape industries—construction is just the start.
SMBs often get stuck experimenting without impact—“pilot purgatory.”
A real AI strategy means aligning tools with workflows, training staff, and managing data.
Early, focused wins (e.g., automating scheduling) build momentum and capacity.

AI Disruption: What Microsoft’s Job Report Means for SMBs

Microsoft’s study of 200,000+ Copilot interactions revealed which jobs AI is most likely to disrupt. High-risk: paralegals, clerks, and bookkeepers. Lower-risk (for now): electricians, plumbers, and other manual trades.

For SMBs, the lesson is urgency: jobs tied to repetitive information processing will change fast. Planning for AI integration isn’t optional—it’s survival.

Trunk Tools: “ChatGPT for Construction”

New York startup Trunk Tools raised $40M to automate construction site workflows like scheduling and documentation. It’s a prime example of how purpose-built AI agents outperform generic tools by adapting to industry-specific needs.

For SMBs, the message is clear: don’t just adopt off-the-shelf solutions. Look for (or build) tools that solve your problems.

Escaping Pilot Purgatory: Build a Real AI Strategy

Too many businesses tinker with AI but never embed it into workflows. This “pilot purgatory” wastes time and money.

Instead:

Start with business goals → align AI projects with ROI.
Map workflows → ensure AI fits into real processes.
Train & align teams → avoid resistance and wasted adoption.
Focus on small wins → automate scheduling, document management, or basic marketing tasks.

As Jim said, “If you start with fundamentals and then ask how technology can help you get there, you’ll develop a roadmap that actually works.” (at 17:19)

Where SMBs Can Beat Big Business

Large enterprises have resources—but SMBs have agility. The ability to pivot quickly, adopt efficiently, and integrate AI into core processes is a competitive advantage.

Jeremy summed it up: “This is where small and medium-sized businesses can win against their larger competitors. They’re going to win—if they’re prepared.” (at 12:09)

Transcript Highlights

“Not just having an AI strategy is not learning how to prompt ChatGPT.” (at 08:04)
“If you just start with mission, vision, values... then ask how technology can help, that’s where you build a roadmap.” (at 17:19)
“Don’t chase fads. Start small, pick a project with early wins, and ladder those up to a bigger strategy.” (at 22:17)

FAQ

What is “pilot purgatory”? It’s when SMBs experiment with AI tools but never integrate them into workflows—wasting time without ROI.
Which jobs are most at risk from AI? Clerical roles like paralegals, clerks, and bookkeepers face high disruption risk. Trades like plumbers and electricians are safer—for now.
What’s an example of a small AI win? Automating staff scheduling or client document management—saves hours each week and builds confidence.
Should SMBs build AI in-house? Usually not at first. Outsourcing or using consultants is often more cost-effective than hiring an internal AI team.
How can SMBs beat big companies in AI? By being nimble: adopting quickly, focusing on ROI, and customizing AI tools for their niche.

Next Steps for SMB Leaders

📌 Start with your top 3 pain points—pick one and find an AI solution that fits.

📌 Align every AI project to a business goal, not just curiosity.

📌 Build momentum with small wins and scale from there.

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