Two Clocks Are Running on Every Signal in Your Queue

Scan: August 22–29, 2026

The Two Clocks

Every signal here runs on two clocks. The first is posting age, how long the role has been public. The second is candidate-advantage decay, how fast your position erodes relative to the people who will apply after you.

They rarely run at the same speed. A Staff role posted three days ago at a twenty-five-person Series A may have already burned half its advantage window, because at that headcount the referral pipeline closes roles in days. Stripe posted eleven days ago and you still have weeks, because their evaluation process hasn't produced a shortlist yet.

This queue ranks by compound decay: where both clocks run fast, you move first. Each entry carries signal age, what waiting seven days costs you, one action verb, the question whose answer changes your approach, and a date.

Act Now

1. Gray Swan AI — Staff Product Designer

What changed: Gray Swan, a ~25-person AI security company (Series A, Wing/Madrona-led), posted a Staff Product Designer role alongside an existing Product Designer opening. AI safety is the core product here, not a feature.

Why it matters: Your Trust essay names the design problem they're hiring someone to solve. The design team is small: Meredith McDermott (Head of UX, ~14 months) plus at least one other designer. The Staff hire will define how design operates rather than inherit a playbook.

Confidence: Moderate (posting confirmed; team size inferred from public profiles and posting language).

Window: Roughly 5–10 days of advantage left. At twenty-five people, a role can close within two weeks of posting without anyone updating the listing.

• Signal age: Active as of August 29; exact posting date unconfirmed. This sits in Act Now because of the second clock, not the first. McDermott's network is the timer.
• Candidate-advantage assessment: If she surfaces a strong referral, the posting closes quietly. Seven days is enough to arrive after the shortlist is set.
• Action: Message McDermott.
• Information objective: Is this the third or fourth design hire, and does the Staff designer report to McDermott or to a product/engineering lead?
• Deadline: September 2.

Move:

• (a) Who: Meredith McDermott, Head of User Experience. In a January 2026 Dscout session, she discussed involving UX from the start of AI product development and using red-teaming to expose failure modes without blocking production.
• (b) Warm path: Cold.
• (c) Opening message: "Meredith — your Dscout session on using red-teaming and evaluations to surface AI failure modes without blocking production described the design problem I've spent the last two years on. I wrote 'Trust Is the New Interface,' mapping five handoff points where AI systems need designed trust boundaries, and I've built the interaction patterns and decision flows for those boundaries through three production agent products at Agentic Labs. Happy to share the interaction models, particularly the inference-aware UX and agent infrastructure work, if that's useful context. Would you have 20 minutes next week to talk about the Staff role and how you're scaling design at Gray Swan?"
• (d) What not to say: Don't offer to bring "design maturity" to a small team. McDermott has been building this function deliberately for over a year. Frame as joining and extending.

Tier Playbook: Read AI-native playbook before outreach. Battlecard candidate — none exists yet.

2. Within — Staff Product Designer

What changed: Within (formerly Klarity, Series B, $90M, 7x growth) posted a Staff Product Designer role. The company builds enterprise process intelligence and context infrastructure for AI agents: a continuously updated graph of people, processes, systems, and judgment calls that agents can query. DoorDash, ServiceNow, and Tyler Technologies are customers.

Why it matters: A Staff posting at a Series B growing 7x with a small design team says design is gaining organizational weight but hasn't settled its operating model at this scale. The title carries real scope. And the design problem — making captured organizational judgment, automation opportunities, and agent behavior legible and controllable to enterprise users — maps onto your Agentic Labs work on agent traces and auditability plus your Alibaba enterprise proof.

Confidence: Moderate (posting confirmed; company context from primary sources; team structure and reporting line thin).

Window: Roughly 7–12 days. The informal pipeline at this stage moves faster than the formal one.

• Signal age: Active as of August 29; exact posting date unconfirmed. Second clock again: Subramaniam is publicly inviting AI product-design candidates to contact her, which means the network pipeline is already running.
• Candidate-advantage assessment: A week's delay risks the shortlist filling through direct referral before you're in the conversation at all.
• Action: Message Subramaniam.
• Information objective: Does design report to product or engineering, and is this scoped as player-coach or pure IC?
• Deadline: September 3.

Move:

• (a) Who: Nithya Subramaniam, Senior Product Designer / Product Design Leader, ~1 year at Within. Her April 2026 article argues that shipping fast doesn't answer why users stay with a product.
• (b) Warm path: Cold.
• (c) Opening message: "Nithya — your piece on fast shipping not answering why users stay lands on something I keep hitting in agent design: the hard UX question isn't whether the agent completed the task, it's whether the user trusts it enough to delegate the next one. I wrote 'Trust Is the New Interface,' mapping five handoff points in agent-human interaction, and I've designed the interaction models and decision flows for those boundaries through three production agent products at Agentic Labs, particularly around agent infrastructure as UX and human-agent system design. Before that I led design and research for Alibaba.com's North America platform at $50B+ GMV. Company Brain sits at the intersection of both. Happy to share the design artifacts. Free next week?"
• (d) What not to say: Don't use the Klarity-to-Within rebrand as a conversation opener. The team lived through it.

Tier Playbook: Read AI-native playbook before outreach. Battlecard candidate — none exists yet.

3. Vanta — Director of Product Design, TPRM

What changed: Vanta posted a Director of Product Design role for Third-Party Risk Management while the Head of Design posting remains unfilled. Former VP of Design Deb Kawamoto confirmed publicly that she left at the end of June and called the Head of Design opening her backfill. No replacement has been announced.

Why it matters: The Director role sits beneath an open leadership vacancy, and that vacancy runs on a clock of its own. Fill the Head of Design next week and the Director's reporting line, mandate scope, and evaluation criteria all move. Get into the conversation while those are still unsettled. Details in the Vanta Battlecard.

Confidence: High (departure confirmed first-person; Head of Design posting still live; no hire announcement located).

Window: The Head of Design search has been open ~54 days. It could close any week, and when it does the Director's parameters lock. You have days of ambiguity left, not weeks.

• Signal age: Director posting ~4 days (published August 25); Head of Design posting ~54 days (Kawamoto departure late June).
• Candidate-advantage assessment: Right now the committee evaluating the Director doesn't know who the Director will report to. That's your opening to shape the scope conversation. Seven days from now, someone else may have defined it for you.
• Action: Message Epling.
• Information objective: Does the Director report to the incoming Head of Design, or directly to Epling until the Head is hired? That determines whether you're pitching a peer relationship or a subordinate one.
• Deadline: September 4.

Move:

• (a) Who: Jeremy Epling, Chief Product Officer, ~3 years at Vanta. In a First Round interview, he argues that senior product leaders must stay close to product details and that rigid hierarchies damage decision quality.
• (b) Warm path: Cold. Vanta investors include Sequoia, Craft Ventures, Y Combinator, but no person-level bridge to your networks turned up.
• (c) Opening message: "Jeremy — your First Round piece on staying close to product details and resisting rigid hierarchy describes the kind of design leadership I practice. At Alibaba.com I led design and research for the North America platform at $50B+ GMV, staying hands-on with the product while building the function. I'm interested in the Director of Product Design role for TPRM and would value understanding how you're thinking about the design leadership structure as the Head of Design search progresses. Would you have time for a brief conversation?"
• (d) What not to say: Don't ask whether the Head of Design role is filled. That signals you're evaluating org stability rather than the product problem. Ask about the Director's reporting structure instead and you'll learn the same thing.

Tier Playbook: Read Growth-stage platform playbook before outreach.

Act Soon

4. OpenAI — Growth, Codex

What changed: OpenAI posted a product design role for Growth and Codex. Two days earlier, Head of Product Design Ian Silber described the core interaction problem as helping people express intent into a largely blank interface while assembling experiences from reusable primitives.

Why it matters: Silber's interview is the real job description. It tells you what he evaluates — curiosity, systems thinking, hands-on prototyping, a point of view about AI-native product behavior — and what he doesn't require, which is prior AI-company tenure. Your Trust essay and forward-looking artifacts speak to the stated criteria without translation.

Confidence: High (Silber interview confirmed and dated; posting corroborated within 48 hours of the interview).

• Signal age: ~11 days (Silber interview August 16; posting ~August 18).
• Candidate-advantage assessment: OpenAI runs a structured, high-volume process, so your position doesn't decay from pipeline speed. It decays from freshness. Every week more applicants read that interview and hand his language back to him. You have roughly two weeks before quoting it reads as common knowledge rather than engagement.
• Action: Apply and message Silber.
• Information objective: Is this scoped as IC or player-coach, and does it sit within the ChatGPT product surface or the Codex developer surface?
• Deadline: September 8.

Move:

• (a) Who: Ian Silber, Head of Product Design, ~3 years. His August 16 interview emphasizes curiosity, systems thinking, hands-on prototyping, and a developed point of view about AI-native product behavior over prior AI-company tenure.
• (b) Warm path: Cold.
• (c) Opening message: "Ian — your conversation about designing for intent expression into a blank interface, and building from composable primitives rather than accumulating features, describes the problem I've been prototyping against. I published 'Trust Is the New Interface,' mapping five handoff points in agent-human interaction, and I've designed the interaction models, decision flows, and state diagrams for those boundaries through three production agent products at Agentic Labs: inference-aware UX, intent-based interaction, agent infrastructure as UX. Happy to share the artifacts if they'd be useful context. Before that I led design and research for Alibaba.com North America at $50B+ GMV. I'd welcome a conversation about the Growth-Codex role."
• (d) What not to say: Don't lead with a feature-additive portfolio narrative. Silber's criteria reward subtraction, reuse, and composability, so a case study about adding a feature is structurally misaligned. (His evaluation surface is covered in the OpenAI Battlecard.)

Tier Playbook: Read AI-native playbook before outreach.

5. Capital One — Director, Product Design, AI in Experience Design

What changed: VP Design Patrick Dohan posted the Director mandate, describing it as combining long-range strategy with immediate milestones, technical depth, hands-on execution, and experimentation bias at enterprise scale. The role has been through multiple iterations since May, with the language shifting from visionary CDO-peer framing toward operational enablement infrastructure.

Why it matters: Three months unfilled means the committee has calibrated through failure and the pipeline is thin at reset. The move from "visionary" to "enablement" tells you what the first slate lacked: operational proof at scale. Your Alibaba enterprise work and TinyFish production experience answer the revised criteria.

Confidence: High (Dohan's post confirmed and dated; search history tracked across three iterations with documented language shifts).

Rubric note: Capital One is public, so there's no equity upside. The role clears Watch on role score alone: AI exposure quality (designing how AI embeds into a 200+ person design org) and scope expandability (Jorge is building a new capability layer with no ceiling defined yet).

• Signal age: Dohan's post is recent (late August). The underlying search has run ~3 months across iterations.
• Candidate-advantage assessment: Early candidates matching the revised language get outsized attention on a reset search. Capital One's process is slow and structured, so you have two to three weeks before the first-round slate is set.
• Action: Apply and message Dohan.
• Information objective: Has the seniority ceiling moved since the earlier iterations? The visionary-to-enablement shift suggests it may have. Confirm whether this is a peer to the design leadership team or a layer below.
• Deadline: September 12.

Move:

• (a) Who: Patrick Dohan, VP, Design, Premium. Executive buyer: Daniela Jorge, SVP and Chief Design Officer (~3 years). In a March 2026 interview, Jorge discussed keeping people central as AI changes design work. Prior analysis indicates Jorge screens for organizational navigation: patience, listening before prescribing, cross-functional credibility.
• (b) Warm path: Cold.
• (c) Opening message: "Patrick — your description of this Director role as combining long-range AI strategy with immediate milestones and hands-on execution at enterprise scale matches how I've operated in two very different contexts: leading design and research for Alibaba.com's North America platform at $50B+ GMV, and most recently shipping AI-native enterprise tools in production as Head of Product at TinyFish. I'm drawn to embedding AI capability into an existing design organization at Capital One's scale rather than building from scratch. Happy to share how I've approached that bridge between strategic direction and operational proof."
• (d) What not to say: Don't lead with portfolio craft or visual artifacts. Jorge filters on organizational navigation, and a candidate who opens with their best case study is answering a question this committee isn't asking.

Tier Playbook: Read Enterprise platform playbook before outreach.

6. Superhuman — Staff Product Designer, Education Agents

What changed: Superhuman posted a Staff Product Designer role for Education Agents.

Why it matters: "Education Agents" implies agents that teach users rather than execute for them, which is a trust-design problem: the agent has to demonstrate competence without overriding user autonomy. Your Trust essay's handoff framework applies directly, and the 0-to-1 scope maps to your BCG DV build pattern.

Confidence: Moderate (posting confirmed; Education Agents as a product line appears in no public Superhuman material, so scope is inferred from the title and Cannon's public framing of writing agents as augmentation tools).

• Signal age: Active as of August 29; exact posting date unconfirmed. Superhuman's design org is more structured than the Series A companies above, which slows the second clock.
• Candidate-advantage assessment: Waiting a week doesn't cost you the shortlist here, it costs you the definition. This product line is undefined enough that early candidates influence how the role gets scoped.
• Action: Message Cannon.
• Information objective: Is Education Agents a new product line or a feature inside the existing email product? That determines whether the role is 0-to-1 or iteration.
• Deadline: September 10.

Move:

• (a) Who: Kevin Cannon, Design Director, AI Agents, ~1 year at Superhuman. In a 2026 Maven session, he described starting with working AI prototypes, spending less time in Figma, and treating roles across design, product, and engineering as increasingly fluid. He frames writing agents as helping people become better writers rather than replacing their writing.
• (b) Warm path: Cold.
• (c) Opening message: "Kevin — your Maven session on starting from working AI prototypes and treating design, product, and engineering as fluid describes how I worked at TinyFish, where I shipped an enterprise agent platform from zero as Head of Product. I've designed the interaction models and decision flows for agent trust boundaries across three production products at Agentic Labs, including how agents teach and augment rather than replace, which seems central to Education Agents. I wrote 'Trust Is the New Interface' mapping the handoff points where these systems need designed trust. Happy to share the artifacts. Free for a conversation about the Staff role?"
• (d) What not to say: Don't offer to bring process or structure. Cannon's public position is explicitly anti-process — prototypes first, Figma later, fluid roles — so open with what you've built, not how you'd organize the team.

Tier Playbook: Read AI-native playbook before outreach. Battlecard candidate — none exists yet.

7. Headway — Provider Design Cluster

What changed: Headway clustered three provider-side design postings within a short window, indicating a build-out of the provider experience team under Roland Tiangco, Director of Provider Product Design.

Why it matters: A cluster means they're building a team, not filling one seat. The first hire sets the craft bar and usually influences who comes next. Your regulated-domain proof and the Trust essay's three-party delegation framework map onto Headway's provider-platform-patient structure, where per-action review is structurally impossible.

Confidence: Moderate (cluster confirmed from prior cycle; Tiangco's appointment confirmed via VP Product post; individual posting ages are approaching the 14-day cluster-decay threshold and should be re-verified before you send).

• Signal age: ~7–14 days (surfaced in the August 22 Signal Watch).
• Candidate-advantage assessment: The window is wider than a single posting because they're hiring several people. What you lose by waiting is the bar-setting hire, which is the one worth having. Two to three weeks before the initial slate gets evaluated.
• Action: Message Ellen Dong. Tiangco has no public fingerprint to open on.
• Information objective: Is the consolidated provider role a senior IC embedded in Tiangco's team, or a player-coach expected to hire beneath them?
• Deadline: September 12.

Move:

• (a) Who: Ellen Dong, Head of Design. Joined Headway January 2022 as its first designer; now leads Product Design, Creative, and Research. Her portfolio names "taste and craft" as explicit hiring criteria and says a candidate's questions reveal the depth of their thinking.
• (b) Warm path: Cold.
• (c) Opening message: "Ellen — I've been following Headway's provider-side build-out and the design challenge underneath it: trust boundaries for a three-party system where the provider, the platform agent, and the patient each need different levels of control and visibility. That's the problem I mapped in 'Trust Is the New Interface' and built against in regulated contexts — pharma supply chain at Thermo Fisher (100% adoption, $20M+ margin impact) and disaster relief disbursement at the American Red Cross ($847K disbursed, national deployment), both as Product Design Director at BCG Digital Ventures. I'd welcome a conversation about the provider design roles and what you're looking for in this phase of the team."
• (d) What not to say: Don't characterize Headway's provider experience as broken or immature. Dong built this function from zero and takes visible pride in the team.

Tier Playbook: Read Healthcare/Regulated playbook before outreach.

Watch

Stripe — Senior Staff Product Designer, Data & AI. Active posting, ~14 days old. Katie Dill (Head of Design, ~5.5 years) and Eeke de Milliano (Head of Product, Data & AI) are the visible routes, but no design-level hiring manager has been identified for this specific role. Stripe's structured process means your position decays slowly here. Tier archetype: Enterprise platform. Escalation trigger: identification of the design manager sitting between Dill and this role, or a public "I'm hiring" post from a Data & AI design lead.

Deprioritize

• Stepful / Outreach: Below cash floor. Remove from active tracking.
• Gusto: Head of Design posting aging toward the 43-day stale threshold with no new signal. Revisit only on a leadership hire announcement or a posting refresh with changed language.
• Midjourney: Design Lead posting approaching the Ignore threshold. No new organizational signal. Revisit if a design leadership appointment surfaces.

Window Status Changes