01. The 2026 Market Pattern
Marc Sumner (Robertson Sumner) identified that the rarest and most in-demand roles are those blending technical literacy with commercial acumen and soft skills. In 2026, AI fluency is no longer a "plus"—it is the baseline. Human judgement has become the primary differentiator in high-value enterprise sales.
The McKinsey Ownership Rule
Elite firms now screen for individuals who "maintain ownership of decisions when AI outputs are imperfect." Success is no longer measured by how well you use the tool, but by how you orchestrate human-agent workflows to deliver a superior outcome.
02. The Strategic Hierarchy
Companies do not buy products; they buy to implement initiatives that support their strategies and goals. Most sellers fail because they stay at the Department level, missing the bigger picture.
GOALS
Vision, Financial Targets, & Board-level Imperatives.
STRATEGIES
The Strategic Pillars & Competitive Positioning.
INITIATIVES
Funded Transformation Programmes & Specific Projects.
DEPARTMENTS
Operational Activities & Daily Execution.
The Management Gap
High-value deals exist in the Management Gap: the distance between what the CEO promises the market (Goals/Strategies) and what the 10-K Risk Disclosures actually report (The internal friction hindering Initiatives).
03. The Intellectual Bedrock
Insight-Led Selling | Timme & Astley
Adopting an Executive Mindset. This is the shift from "What am I selling?" to "What are they trying to solve?". You must speak the language of the Boardroom (CFO-English) rather than vendor jargon.
Tactical Empathy & The Accusation Audit | Chris Voss
Surface their project anxieties or past failures before they do. By identifying the internal friction (found in the Management Gap) and naming it, you build immediate trust and "negotiate" the truth of the situation.
The Sinatra Test | Heath Brothers
Your messaging must be Concrete and Credible. If you can solve their most "Boring but Expensive" technical debt or risk issue, you prove you can solve anything. Use one-shot authority to win the room.
Blue Sky Thinking
Elevating the narrative from tactical "feature selling" to solving for the Global Imperative. This is the discipline of mapping a single migration or product to the company's "North Star" goal—ensuring the solution ripples across the entire enterprise.
04. The 8-Pillar Protocol
The institutional-grade due diligence checklist used to perform a 360-degree account scan.
The Executive Library
Foundational texts and mental models that underpin this Operating System.
Human Amplification Index™
Sol Rashidi: Defines the critical boundary between what AI should automate (The Dull & Difficult) and what humans must own (The Distinct & Emotional).
Second-Order Thinking
Howard Marks: A mental model for moving beyond the immediate effects of a deal to the ripple effects across the enterprise risk profile.
Made to Stick
Heath Brothers: The foundation of the Sinatra Test—ensuring messaging is concrete, credible, and carries "one-shot" authority.
Never Split the Difference
Chris Voss: Applying high-stakes negotiation tactics to commercial environments to surface the "Unspoken Needs" of a buyer.
Honesty Check: When AI Gets It Wrong
Maintaining executive credibility requires knowing the failure modes of the tools you use:
- Hallucinations: If AI cannot cite a page number, quote, or transcript, the insight does not exist. Always verify data against the source.
- Context Collapse: AI models often struggle with real-time personnel changes. Always verify executive roles on LinkedIn before outreach.
The foundations are set. Now, deploy the tools.
PROCEED TO WEEK 1