Jack Damon

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Working with AI: Lessons from software’s head start

On Monday, October 26, I gave this talk at a dinner hosted by With Coverage. It explores parallels between AI adoption in software engineering and financial knowledge work, using Excel as finance’s equivalent of the IDE to map four stages: AI assists, collaborates, executes, and coordinates. These are broad generalizations, but software’s head start offers useful clues about where non-programming knowledge work workflows may be headed and how to prepare as an individual and organization.

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Working with AI: Lessons from software’s head start. Title slide, October 2026.
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Parallel timelines for software engineering and financial knowledge work introduce the deck’s estimated 12–18 month adoption lag.
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Timeline adds stage 1, AI assists: copying code and Cursor’s March 2023 launch.
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Spring 2023: Cursor’s inline code editing illustrates AI assisting within the existing programming workflow.
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Timeline adds stage 2, AI collaborates: Cursor Agent launches in November 2024.
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Fall 2024: Cursor Composer’s code diffs and chat illustrate AI collaborating within the programming workflow.
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Timeline adds stage 3, AI executes: highly capable coding models and mainstream Claude Code adoption in late 2025 and early 2026.
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Winter 2025: Claude Code, an Anthropic headline, and an Andrej Karpathy post illustrate a shift toward agents executing independently.
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Timeline adds stage 4, AI coordinates: Cognition and Factory cloud agents and swarms in 2026.
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A rising monthly usage chart and Cognition and Factory headlines illustrate the 2026 shift toward autonomous cloud workforces.
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Timeline adds Excel’s first stage: copying and pasting formulas from ChatGPT during 2023–2025.
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Timeline adds Excel’s collaboration stage, showing Shortcut’s July 2025 demo and Claude in Excel in October 2025.
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Excel’s Cursor Agent moment: side-by-side screenshots of Shortcut and Claude in Excel.
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Four-stage timeline comparing software engineering and Excel AI, marking financial knowledge work at the transition toward independently executing agents.
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Is Excel approaching its end-to-end agent moment?
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How long until spreadsheet users spend most of their work without the actual spreadsheet open?
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Timeline adds a possible 2027 coordination stage and asks what a Cognition or Factory equivalent for knowledge work will look like.
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Cloud agents are independent, proactive, and scalable: they work without an open laptop, respond to triggers, and delegate across workers.
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A two-column table pairs lessons from software teams with ways finance teams can prepare.
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First lesson: bottlenecks shift from producing work to reviewing it, increasing the importance of reviewing AI outputs.
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A second lesson: institutional knowledge becomes infrastructure, so firms should document implicit knowledge and make it accessible.
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A third lesson: delegation becomes a core skill; train managers on AI tools and individual contributors on delegation.
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Screenshot of Cognition’s article on allocating AI spending by efficiency, with guidance to reward efficient users and coach others.
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A green callout beside the article says efficient AI users should receive more AI spending.
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A blue callout says less efficient AI users should receive coaching to improve.
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The preparation table adds a fourth lesson: greater individual capability changes team design, so reconsider team composition.
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