Ramp — Director, Product Design
Ramp's Director, Product Design posting is 25 days old and describes a leader who ships PRs, designs memory, and builds with agents. Tuesday July 8 is your outreach window — holiday weekend clears the inbox. The non-obvious angle here: Ramp's VP Design publicly celebrates users spending less time in the product. Competing candidates will pitch engagement. Pitch vanishing instead. Your Alibaba agentic vision plus trust ladder are the rare combination that makes that positioning credible at $200B+ in annualized spend.
Ramp — Director, Product Design
Ramp's Director, Product Design posting is 25 days old and describes a leader who ships PRs, designs memory, and builds with agents. Tuesday July 8 is your outreach window — holiday weekend clears the inbox. The non-obvious angle here: Ramp's VP Design publicly celebrates users spending less time in the product. Competing candidates will pitch engagement. Pitch vanishing instead. Your Alibaba agentic vision plus trust ladder are the rare combination that makes that positioning credible at $200B+ in annualized spend.
Headway — Design Director, Provider Experience
Headway's provider platform now generates AI-drafted progress notes, insurance flags, and scheduling recommendations. Every output carries clinical and financial consequence for the provider who signs it. Their Design Director, Provider Experience posting (Ashby, June 4) is 29 days old, past the calibration phase, and landing in a holiday-compressed window. Lead with Thermo Fisher's exception-first architecture. Bridge to the Trust essay. Send Tuesday morning, July 8. The non-obvious signal: a parallel director search open nine months tells you what this committee actually evaluates.
Headway — Design Director, Provider Experience
Headway's provider platform now generates AI-drafted progress notes, insurance flags, and scheduling recommendations. Every output carries clinical and financial consequence for the provider who signs it. Their Design Director, Provider Experience posting (Ashby, June 4) is 29 days old, past the calibration phase, and landing in a holiday-compressed window. Lead with Thermo Fisher's exception-first architecture. Bridge to the Trust essay. Send Tuesday morning, July 8. The non-obvious signal: a parallel director search open nine months tells you what this committee actually evaluates.
The Posting Moved. Capital One's AI Design Problem Stayed.
The AI in Experience Design Director posting at Capital One no longer surfaces in their careers page search as of today — though the direct URL still resolves and a new Senior Director, Research & User Intelligence role posted two weeks later points back to it. The posting is liminal. The organizational problem it was created to solve is fully intact: who governs AI adoption across a several-hundred-person design org? That mandate has been publicly visible and unfilled since February. The limbo works in your favor. Lead with the problem, independent of any req. Send Tuesday July 8.
The Posting Moved. Capital One's AI Design Problem Stayed.
The AI in Experience Design Director posting at Capital One no longer surfaces in their careers page search as of today — though the direct URL still resolves and a new Senior Director, Research & User Intelligence role posted two weeks later points back to it. The posting is liminal. The organizational problem it was created to solve is fully intact: who governs AI adoption across a several-hundred-person design org? That mandate has been publicly visible and unfilled since February. The limbo works in your favor. Lead with the problem, independent of any req. Send Tuesday July 8.
Handoff Diagnostic
Every company on your list says AI. You need to know which ones have operationalized accountability before you spend positioning energy. These three questions work in any first conversation.
"When something the AI does turns out to be wrong — where does that go?" Listen for an incident path. Companies that have operationalized AI name a team, a process, a change that happens before the next run. Vague answers about model improvement mean nobody owns failure.
"Walk me through a workflow where AI takes action — at what point can a human stop it before it's committed?" Listen for whether they distinguish reversible from irreversible actions. Human gates belong at the commitment threshold, not after.
"Who decided how AI gets used in core workflows — was design part of that decision, or did design come in after?" The mandate question. You're learning whether this role shapes the operating model or decorates one that Legal, Product, and Engineering already locked.
Ask all three. Concrete answers on all three mean they've thought about AI as something to govern. Abstract answers on all three mean they're hiring you to make AI features look trustworthy.
