Scan: September 13–19, 2026 | Shelf life: Act entries through September 26
Sorted this issue by demand type — what each role screens for — rather than by company. Thirteen signals, four demand families.
Your proof maps unevenly across them. Agent trust is where you have an edge over most of the slate. Enterprise coherence needs you to lead with Alibaba rather than the AI work. AI production infrastructure may be a credential boundary, and no reframe fixes that.
Five signals score Act Soon; five more cross their decay boundary before the next issue. Nothing qualifies as Act Now — no signal this week both clears the Act rubric threshold and sits in a confirmed window closing inside seven days.
Monday: Joel Califa at Unify. Strongest route in the queue, cleanest trust-design match. Tuesday: apply to OpenAI Growth–Codex and send Ian Silber a connection request. Wednesday: May-Li Khoe at Handshake, Autonomous Recruiting role.
Agent Trust Design
What these roles screen for: whether you can design interfaces where users hand consequential actions to an AI agent and then leave them there. Your Trust essay names the problem and Agentic Labs shows you've shipped against it — most candidates at this level have one or the other.
Act Soon — Unify: Staff Product Designer
What changed: Unify closed a $40M Series B led by Battery Ventures. The Staff Product Designer listing names Joel Califa as VP Design and direct manager. Califa publicly invited candidates to contact him. He reports to the CEO.
Why it matters: Unify sells an AI-native outbound sales workspace, so the central design question is whether a user trusts AI-generated outreach to speak for them. Califa is building the team from scratch and this is an early Staff hire on a small group. Your essay states the framework; Agentic Labs shows you shipped it.
Confidence: High on route (named in the posting, public invitation). On freshness: I could not determine when the role was posted. Califa's hiring invitation is roughly nine months old, well past the decay window for that signal type. But the listing is live, the Series B closed recently, and the posting names Califa as the manager — the funding round is what refreshes this. Nothing else in the queue combines a named manager, an explicit reporting line to the CEO, and an open invitation to candidates. Take it first anyway, and verify in your first exchange whether the search is still reviewing new candidates.
Window: Open, age unconfirmed. Act this week.
Tier archetype: AI-native. Read AI-native playbook before outreach. | Battlecard: Candidate — flag for creation. | Rubric: Company 12/12 + Role 14/15 = Act. (Act on rubric, Act Soon on urgency, since no confirmed deadline sits inside seven days.)
Move:
(a) Who: Joel Califa, VP Design. Roughly nine months at Unify, joined December 2025. Previously led design at GitHub, so expect him to evaluate craft rigor and systems thinking.
(b) Warm path: Cold.
(c) Multi-channel plan: (1) Engage with Califa's recent LinkedIn content on design team-building. (2) Connection request with the note below. (3) Full message after acceptance. (4) Apply directly in parallel. (5) One follow-up after five business days.
(d) Connection request: "Joel — I published 'Trust Is the New Interface' on designing for AI agent credibility, then shipped three agentic products at Agentic Labs. Building trust into AI-native workflows is the problem I want to keep solving. Would value connecting."
(e) Full outreach message:
Joel,
The design problem at the center of AI-native outbound is whether users trust the AI to represent their judgment accurately enough to let it act. I wrote about this in "Trust Is the New Interface" (junochen.com) and then spent two years building it.
At Agentic Labs, I designed and shipped three production agentic products — Brand Pulse, Retail Velocity, and Carrier IQ — each requiring users to delegate consequential decisions to AI agents. The core design challenge was getting users past the threshold where they stop falling back to manual and start trusting the autonomous mode. That required progressive delegation, transparent reasoning, and human-override architecture that earned trust incrementally.
Before that, I led design and research for Alibaba.com's North American B2B marketplace ($50B+ GMV, +20% transaction growth), where the problem was trust at enterprise scale.
Most recently as Head of Product at TinyFish, I shipped AI-native enterprise tools in production, taking the agentic platform from zero to launch in three months.
I'd welcome a conversation about where Unify's trust gaps are sharpest. Portfolio at junochen.com.
Juno
(f) What not to say: Don't lead with management experience or team-building ambitions. Califa is building the team, and you'd be his first Staff hire. No TinyFish product specifics. Don't headline Alibaba either; Unify is a 30-person company.
Interview prep:
- Expect a portfolio deep-dive on AI interaction patterns, probably with a hands-on exercise. Califa's GitHub background points to craft rigor and systems thinking over strategic narrative.
- Lead with Agentic Labs — whichever product carried the most trust-critical delegation moment.
- Ask: "Where in Unify's current workflow do users most often override the AI's suggestion, and what does that tell you about the trust gap?"
- Your differentiator: a published trust framework plus production agentic proof.
Act Soon — OpenAI: Product Design Lead, Growth–Codex
What changed: The Growth–Codex design lead role remains posted. Ian Silber, Head of Product Design for about three years, has described his hiring criteria: curiosity, hands-on prototyping, composable product primitives for AI-native behavior.
Why it matters: Codex acts autonomously for developers, so the growth problem is getting new users to delegate real coding work to it. Your essay and Agentic Labs map onto that directly.
Confidence: High on fit. Moderate on route — Silber leads product design across ChatGPT and Codex but isn't confirmed as hiring manager for this requisition. Window: Live. Visibility across multiple cycles reads as a high bar rather than a stale search.
Tier archetype: AI-native. | Battlecard: Exists. | Rubric: Company 10/12 + Role 14/15 = Act.
(a) Who: Ian Silber, Head of Product Design. Function-level route, not confirmed for this requisition. (b) Warm path: Cold.
(c) Multi-channel plan: (1) Apply directly — the official application is the only confirmed permissioned route. (2) Connection request to Silber with the note below. (3) Full message after acceptance. (4) One follow-up after five business days.
(d) Connection request: "Ian — your framing of composable primitives for AI-native behavior mirrors the trust architecture I built across three agentic products at Agentic Labs. Interested in the Growth–Codex lead role. Portfolio at junochen.com."
(e) Outreach message:
Ian,
The Growth–Codex design challenge is trust at the adoption edge — convincing developers who've never used an autonomous coding agent to delegate real work to one. I've been designing for exactly this transition.
At Agentic Labs, I shipped three production agentic products where the core problem was getting users past the "I'll just do it myself" threshold. I wrote "Trust Is the New Interface" (junochen.com) to articulate the framework that emerged — how trust calibration, not feature density, determines whether users adopt agentic workflows.
Before that, I led design for Alibaba.com's B2B marketplace ($50B+ GMV). Most recently as Head of Product at TinyFish, I shipped AI-native enterprise tools in production. Portfolio at junochen.com.
Juno
(f) What not to say: Nothing about OpenAI's organizational controversies. Don't position as a manager. "Growth" scopes this role to acquisition and activation, so don't assume it covers Codex broadly.
Interview prep:
- Lead with Agentic Labs, framed on the new-user trust moment.
- Ask: "What's the current drop-off point where new Codex users revert to manual coding?"
- Silber values hands-on prototyping. Bring process artifacts, not finished screens alone.
Act Soon — Handshake: Staff Product Designer, Autonomous Recruiting
What changed: The Autonomous Recruiting role is live. Users move among conversational AI, agentic automation, and structured enterprise tools inside recruiting workflows. Your Agentic Labs portfolio is direct proof.
Prior issues carried inconsistent route information on Handshake's design leadership. Current research resolves it to May-Li Khoe, VP of Design, at moderate confidence.
Confidence: Moderate. Khoe announced she was building the design team roughly a year ago, but neither current posting confirms her as the hiring manager. Window: Live, posting date unconfirmed.
Tier archetype: Growth-stage platform. | Battlecard: Exists. | Rubric: Company 9/12 + Role 13/15 = Act.
(a) Who: May-Li Khoe, VP of Design, about a year in seat. Function-level route. (b) Warm path: Cold.
(c) Multi-channel plan: (1) Apply directly. (2) Connection request to Khoe with the note below. (3) Full message after acceptance. (4) One follow-up after five business days.
(d) Connection request: "May-Li — I've shipped three agentic products where users delegate consequential decisions to AI (Agentic Labs, junochen.com). Handshake's Autonomous Recruiting is the same design problem in a new domain. Interested in the Staff role."
(e) Outreach message:
May-Li,
Autonomous recruiting is an agent trust problem: employers need to believe the AI's judgment is good enough to act on their behalf in a high-stakes decision. I've been designing for this dynamic across three production agentic products at Agentic Labs (Brand Pulse, Retail Velocity, Carrier IQ), where the design challenge was calibrating user trust in autonomous AI actions — progressive delegation, transparent reasoning, human-override architecture.
Most recently as Head of Product at TinyFish, I shipped AI-native enterprise tools in production. Portfolio and Agentic Labs case studies at junochen.com.
Juno
(f) What not to say: Never "job board." Don't lead with Alibaba; enterprise scale isn't the match here.
Interview prep:
- Lead with Agentic Labs, framed on delegation and trust calibration.
- Ask: "What level of autonomy does the recruiting agent currently have, and where do employers most often want to intervene?"
- Handshake is a marketplace. Show that you treat employer trust and candidate experience as coupled problems.
Watch
Within — Staff Product Designer. Series B ($70M, Nat Friedman and Daniel Gross co-led). Tara Ting, Head of Product Design, is the function-level route, corrected from Nithya Subramaniam in Issue 10. Clears Act on rubric (Company 9/12, Role 12/15), but posting freshness is unconfirmed. Escalation trigger: a confirmed posting date, or Ting posting about hiring. AI-native. Battlecard candidate.
Brex — Staff Product Designer, AI. New role-level signal at a previously downgraded company. The Capital One acquisition caps the equity thesis that made Brex attractive. Matt Bango, CDO, reports to the CEO. Posted around Sept 2, crossing the 21-day boundary by Sept 24. Pursue only if the AI exposure and portfolio value justify the time on their own. Company 8/12, Role 11/15 = Watch. Growth-stage platform. Battlecard candidate.
Enterprise Coherence
What these roles screen for: design quality holding together across large, complicated product surfaces. Alibaba anchors your claim here — $50B+ GMV, Head of Design and Research North America. The companies in this family score lower on the rubric: big public companies, peripheral AI, limited equity upside. Lead with scale and the design function you built.
Act Soon — ServiceNow: Director, Customer and Partner Experience
What changed: Carly Price, Senior Director of Customer and Partner Experience Design, publicly promoted this exact role and directed candidates to apply through the posting. Dantley Davis, SVP Design, about a year in seat, is the senior design leader. Posted around Sept 3, crossing the 21-day boundary by Sept 25.
Why it matters: Price's public promotion and application-first instruction make this the clearest route in this family. The role leads a design team inside a mature product org, which is where your Alibaba scope maps.
Confidence: High on route; Price publicly owns the scope. Moderate on verdict, since the rubric scores Watch. Window: Crossing the 21-day boundary Thursday. Apply before Sept 25 if you're pursuing it.
Tier archetype: Enterprise platform. | Battlecard: Candidate — flag for creation. | Rubric: Company 7/12 + Role 11/15 = Watch. It sits in Act Soon because the decay window forces a decision before the next issue, not because the score improved.
(a) Who: Carly Price, Senior Director, Customer and Partner Experience Design. She has publicly asked candidates to apply through the posting due to volume. (b) Warm path: Cold.
(d) Connection request: "Carly — I led design and research for Alibaba.com's North American B2B marketplace ($50B+ GMV, +20% transaction growth). The CPE Director role maps to how I think about design coherence at enterprise scale. Applied through the posting."
(e) Outreach message:
Carly,
I saw your post about the Director, Customer and Partner Experience role and applied through the posting.
As Head of Design and Research for Alibaba.com North America, I built the design function across a $50B+ GMV B2B marketplace — hiring, establishing the craft bar, and driving coherence across product surfaces that served fundamentally different user workflows. That experience in enterprise-scale design consistency is what I'd bring to ServiceNow's CPE surface.
Before Alibaba, I led 0→1 builds as Product Design Director at BCG Digital Ventures across pharma (Thermo Fisher, $20M+ margin) and consumer platforms (Allē, 30M members). Most recently as Head of Product at TinyFish, I shipped AI-native enterprise tools in production.
Portfolio at junochen.com — happy to discuss how the Alibaba work translates.
Juno
(f) What not to say: Don't open with AI or agentic products. This role screens for enterprise design leadership.
Expiring — Decide This Week
Slack — Principal Architect / VP Product Design IC. Michael Lenahan is the reporting executive, identified since Issue 10. Location conflict unresolved: the employer record says San Francisco only, while Lenahan's public post says "San Francisco, CA (or remote)." Posted around Sept 2, crossing the 21-day boundary by Sept 24. Action this week: if remote eligibility matters, message Lenahan to clarify before spending more outreach time. Don't build an application around a role whose location requirement is ambiguous. Company 7/12, Role 12/15 = Watch. Enterprise platform. Battlecard candidate.
Watch
ServiceNow — Director, ITSM. Paul Hong announced this role, team of 20+. New posting. Escalation trigger: a confirmed posting date inside the hot window. Enterprise platform.
ServiceNow — Principal, SalesCRM and Sr Staff, Security. No confirmed scope-specific routes. Both crossing the 21-day boundary this week. Enterprise platform.
High-Consequence Decision Workflows
What these roles screen for: professional workflows where the user's decision lands on somebody else. Thermo Fisher ($20M+ margin, 100% adoption) and Red Cross ($847K disbursed, national deployment), both as Product Design Director at BCG Digital Ventures, are direct production proof.
Act Soon — Headway: Staff Product Designer, Provider Practice Growth
What changed: The role is live. Route correction from Issue 9: Ellen Dong left Headway for Hera in September 2026. The current route is Roland Tiangco, Director of Provider Product Design, whose scope — onboarding, practice growth, clinical workflows — was announced by Jake Poses roughly six months ago and overlaps this vacancy.
Confidence: Moderate. Tiangco's scope matches, but no public source confirms him as this role's manager, and I could not locate a verified LinkedIn URL. Window: Live. Headway has seven design openings, which reads as active expansion.
Tier archetype: Healthcare/Regulated. | Battlecard: Exists. | Rubric: Company 9/12 + Role 11/15 = Watch. The tier is Act Soon because the signal is active and clears the Act Soon threshold (company 8+ OR role 10+); the verdict reflects the score, the tier reflects timing.
(a) Who: Roland Tiangco, Director of Provider Product Design, about six months in seat. No verified LinkedIn URL. Jake Poses, the product executive who announced him, is the senior sponsor fallback. (b) Warm path: Cold.
(c) Multi-channel plan: (1) Apply directly. (2) Connection request to Poses with the note below. (3) Full message after acceptance. (4) If Tiangco's profile surfaces, send a parallel request referencing the Provider Practice Growth scope. (5) One follow-up after five business days.
(d) Connection request (to Poses): "Jake — I designed high-stakes professional workflows at BCG DV (Thermo Fisher, $20M+ margin, 100% adoption) and led product at TinyFish. The Provider Practice Growth Staff role maps directly. Portfolio at junochen.com."
(e) Outreach message:
Jake,
Provider practice growth is a high-consequence design problem — therapist decisions on Headway directly affect patient access to care. I've spent my career designing for these stakes.
As Product Design Director at BCG Digital Ventures, I led Thermo Fisher's clinical workflow platform ($20M+ margin, 100% adoption across pharma teams) and the American Red Cross disaster relief system ($847K disbursed, deployed nationally). Both required designing decision workflows where the user's choices had immediate consequences for other people.
Most recently as Head of Product at TinyFish, I shipped AI-native enterprise tools in production. Portfolio at junochen.com.
Juno
(f) What not to say: Don't open with AI or agentic work; Headway is a therapy platform. Don't equate pharma regulatory context with mental health. The compliance environments are different, and they'll hear it.
Interview prep:
- Lead with Thermo Fisher and Red Cross, framed on high-consequence professional decisions.
- Ask: "What's the biggest friction point in therapist onboarding that affects whether they stay on the platform?"
Watch
Handshake — Student Experience. Posted around Sept 4, crossing the 21-day boundary by Sept 26. May-Li Khoe is the function-level route. Weaker demand match than Autonomous Recruiting, since the trust-calibration angle doesn't apply as cleanly. Decide by Friday whether to apply alongside the AR role. Growth-stage platform.
Scale AI — Public Sector. No design decision-maker is identifiable at Scale AI: no Head of Design, CDO, or VP Design surfaces anywhere public. KK Kim is a low-confidence functional lead only. Escalation trigger: a design decision-maker surfaces. Company 9/12, Role 10/15 = Watch. AI-native. Battlecard candidate.
AI Production Infrastructure — Capability Boundary
Some roles read as agent trust design but screen for production AI engineering: Python in production, evaluation pipeline design, model fine-tuning. The Anthropic role from Issue 11 is the clearest case — a design title with requirements closer to infrastructure engineering than interaction design. OpenAI's non-Growth Codex postings can carry similar language. When a posting leans on "evaluation architecture," "model training," or "production ML," decide honestly whether you can claim it before spending outreach time. This is a qualification boundary: the credential either exists or it doesn't, and no artifact you build closes it. Route to Counter-Narratives when the boundary is ambiguous.
Window Status Changes
Upgraded:
- Unify → Act Soon (new to queue, top priority this cycle)
- ServiceNow CPE Director → Act Soon (from Watch, on the expiring window plus the Carly Price route)
- ServiceNow ITSM Director → Watch (new posting, Paul Hong as scope owner)
Route corrections:
- Headway: Ellen Dong → Roland Tiangco (Dong left for Hera in September)
- Handshake: prior inconsistency resolved to May-Li Khoe at moderate confidence, not confirmed for either current requisition
- Within: Tara Ting replaces Nithya Subramaniam as function-level route, corrected from Issue 10
Expiring (crossing the 21-day hot-window boundary by Sept 26):
- ServiceNow Security (~Sept 2) and SalesCRM (~Sept 3)
- Slack Principal Architect (~Sept 2)
- Handshake Student Experience (~Sept 4)
- Brex AI (~Sept 2)
All five remain listed on employer-controlled career pages as of September 19. A live listing tells you the application route is open. It doesn't tell you the slate is early, or that a new applicant gets read.
Deprioritize
Nothing from prior cycles decayed past recovery this week. The five expiring signals above move to Deprioritize next cycle unless something refreshes them: a new hiring post, a reposted requisition, a leadership change. Until then, pause outreach on any expiring signal you haven't contacted by September 26.
- Gusto's eight-role cluster: The Senior Staff Finance role posted September 15 screens for consequential financial automation and trust in AI recommendations — strong Trust framework match — while CDO Amy Thibodeau is the confirmed senior design route across all eight openings.
- Rubrik's recruiter-invited submission: Noopur Mer explicitly asked candidates to send résumé and portfolio directly to her for the Director, Product Design role at $250K–$351K, making this one of the few current signals with a named procedural route and a compensation floor that independently clears your threshold.
- Anthropic's capability gate: Chelsea Larsson confirmed she owns the Evals & Prompts hiring and explicitly asked candidates not to DM but to apply through recruiting — the first step is an honest self-assessment on production Python and evaluation infrastructure, not outreach positioning.
- Sol as an early-stage wildcard: Their first product designer posting covers agentic HR with compliance workflows, configurable customer-built agents, and trust boundaries between human and AI action — high Trust framework alignment, but no confirmed funding stage, design leadership, or shipped customer outcomes.