That’s the gap I work in.
From inside Apple, I helped position the company’s AI work to enterprise buyers. Two campaigns I’m proud of: “Mac Does That” (global, blended business+consumer) and “Best AI PC is a Mac” (cross-functional, analyst-backed). I built the Apple Intelligence keynote decks and sales enablement, and ran on-device AI marketing for business customers: the GTM, the content, the internal evangelism team.
Before that, 15 years in the Executive Briefing Program, briefing CEOs, CIOs, CFOs, LOB leaders, and heads of state on technical products. I know how to walk a senior decision-maker through a hard pitch and keep them in the room. Not many people can.
22 years at Apple total. Now I do that work for organizations from outside.
I’m Todd Dailey. Based in San Jose, travel-friendly.
I’m a builder. For 15 years inside Apple’s Executive Briefing Program, I built and delivered customer-facing content for senior business, education, and government leaders. Then I shipped landmark AI campaigns inside Apple’s Worldwide Product Marketing. Concept, code, global rollout, all of it. Now I do that work for organizations from outside.
I’m @twid on Twitter. I worked at Apple from 2003 to 2026. I built my own AI ops layer (Wren) to run my life, which is currently the most over-engineered thing in my house.
Three kinds of project. All boutique, all with a set end date.
You have an operation. AI should be helping. Mostly it isn’t. Your team has the licenses and uses approximately none of them. That’s the work: getting from “we bought ChatGPT” to people reaching for it on a Tuesday. Marketing teams stuck at “look at this cool prompt” get past it. Ops teams get tools they actually use.
Your board, your CFO, your CIO need to understand AI well enough to bet on it. I spent 15 years briefing C-suite executives on technical products at Apple. I shipped AI marketing content end-to-end: concept through VP approval, published worldwide in 21 languages. I know what works in a 2-hour room: keynote decks, live demos, positioning papers, the works.
Production systems, soup to nuts. Flask, Next.js, Fly.io, Postgres, SQLite. AI is in the toolchain because that’s how I work, not because it’s a buzzword. I ship them solo. Recent: spalterdigital.com, browninterviews.org, plus private builds.
How this works: typical engagement is 30–90 days with a clear deliverable. Boutique by design. A small number of projects at a time, not many.
Three things I’m good at:
15 years at the Apple Executive Briefing Program taught me how to make hard technical material land with people who had to bet real money on it: CXOs, CIOs, heads of state. Then Worldwide Product Marketing taught me how to ship that content globally.
People at Apple sought me out as a mentor. I worked with senior people whose calendars are tracked in 15-minute blocks for 22 years without burning bridges. AI projects fail more often on people than on tech. I’ve debugged that side too.
I built custom generative-AI pipelines before the tools existed, and stayed in the work until they shipped. That’s the job: figure out how, then refuse to quit through the part where it doesn’t work yet. Same muscle as shipping anything global inside Apple: invent it, defend it, hold the line until it’s out the door. Core skill working with senior leaders in the Executive Briefing Program and in marketing.
I drove this analyst-led report from concept through global publication on apple.com, coordinating Omdia’s analyst team with PR, Brand, and Legal. The result became Apple’s analyst-led case for on-device AI, distributed via apple.com/business/enterprise as part of Apple’s enterprise sales-enablement.
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todd@dailey.info
@twid on Twitter
Todd on LinkedIn