Session

Before Onboarding AI Agents to Your Team: Lessons from Shopify's "AI-First" Gauntlet

"Before asking for more headcount and resources, teams must demonstrate why they cannot get what they want done using AI." — Tobi Lütke, CEO, Shopify

That single line from Shopify's internal memo has ricocheted through tech organizations worldwide, forcing a critical question every software professional must answer: "Am I better at my job than an AI agent?"

This isn't about job security—it's about strategic positioning in what is becoming an AI-first world. Shopify's bold directive reveals a widening skills chasm that separates those who can partner with AI agents from those who will be left behind. This workshop dissects their approach to help you bridge that gap before it becomes too wide to cross.

The Three-Layer Skills Gap:
Shopify's policy exposes that AI fluency isn't a single credential—it's a complex, layered capability:
• Technical Fluency: Data literacy, prompt engineering, agent frameworks, and LLM API integration
• Strategic Judgment: Deciding where AI creates leverage versus where human insight still matters
• Collaboration: Onboarding agents as teammates who contribute and refine rather than replace

Beyond Compliance -- Toward Competitive Edge:
History favors companies willing to set audacious constraints. The iPhone emerged from "one-hand operation; no stylus." Spotify's innovation came from bandwidth limitations. Shopify's constraint forces teams to develop the meta-skill of rapid AI evaluation, turning every project into a controlled experiment.

Possible Real-World Applications We'll Explore:
• Dev Manager: Partner with AI agents for enhanced product discovery, using agents to gather insights and analyze data while your strategic judgment guides feature prioritization and team development
• Developer: Collaborate with AI agents as "tireless autonomous pair programmers" for intelligent code generation and automated testing, while your architectural creativity drives system design and complex problem-solving
• DevOps Engineer: Leverage AI agents for adaptive micro-lessons and instant system strain diagnosis, while your infrastructure expertise ensures reliable deployment strategies and performance optimization

Learn to use AI agents as bridges, "accelerating learning and amplifying creativity", rather than axes that narrow opportunity. The clock is ticking. The chasm between AI-fluent and AI-fearful grows wider every quarter.

Target Audience:
Software professionals, team leads, and product folks who need to answer Shopify's challenge: "Tell me of a time when you and an AI agent delivered something neither of you could do alone."

What to Bring
• Your laptop or tablet
• A specific work challenge you're currently solving
• Honest reflection on whether you're AI-fluent or AI-fearful
• Readiness to pick up Shopify's gauntlet and prove your irreplaceable value through AI partnership

How We'll Spend Our Time (60 minutes)

• Shopify's Gauntlet Decoded (10 min) - Understanding the three-layer skills gap and why constraints drive innovation
• Skills Chasm Self-Assessment (15 min) - Mapping your capabilities against the technical fluency, strategic judgment, and collaboration layers
• Agent Partnership Mapping (20 min) - Hands-on identification of where AI amplifies vs. replaces your unique value
• Rapid Evaluation Framework (10 min) - Building your systematic approach to AI agent onboarding decisions
• Bridge-Building Action Plan (5 min) - Concrete steps to develop AI partnership skills before the chasm widens

Bill Allen

Startup Co-Founder delivering Product Innovation in Financial Services | Dojo Coach / Software Crafting Coach

Chicago, Illinois, United States

Actions

Please note that Sessionize is not responsible for the accuracy or validity of the data provided by speakers. If you suspect this profile to be fake or spam, please let us know.

Jump to top