The Challenge
An early-stage, venture-backed startup had some team members who sensed generative AI was relevant to their business but could not articulate why or how to act on that instinct. Most of the leadership team was skeptical. The company lacked a structured on-ramp to generative AI, had no shared vocabulary for evaluating AI opportunities, and no plan for translating curiosity into a strategy or product direction. The result was inaction and risk of missing a critical window.
What They Built
Justin Massa ran a structured AI grounding workshop for the leadership team, followed by one-on-one executive coaching sessions with individual AI playbooks, culminating in a functional AI-first product prototype in under three months.
Justin Massa began with a grounding workshop that oriented the entire leadership team in the strategic direction of the major AI research labs and what that trajectory meant for their specific business. He introduced a three-tier framework to give leaders a shared vocabulary: techniques (skills taught to employees), jigs (lightweight shared tools built in hours), and tools (commercial software with ROI requirements). This framework let the team evaluate AI opportunities without technical background. Following the workshop, Justin moved to one-on-one executive coaching sessions, working with each leader to identify how AI applied to their most important daily work and building personalized AI playbooks. He identified a specific AI capability directly tied to the startup's competitive differentiation and guided the team to explore it deeply — ultimately informing a full company pivot to an AI-first product direction. He remained available as an on-demand resource between sessions. Tools used included NotebookLM, Gemini, ChatGPT, Claude Projects, Bolt.new, Code.dev, and Replit. All leadership skeptics converted to AI believers within the grounding phase.
SMBs (up to ~500 employees) and smaller teams within mid-market and Fortune 500 companies whose executive leadership is curious about AI but overwhelmed, has run scattered experiments without strategic coherence, or has been burned by prior AI or consulting engagements. Best engaged at the CEO/COO/Managing Partner/CFO level.
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