Scan window: June 26 – July 3, 2026 Shelf life: Through July 11. Outreach optimized for Tuesday, July 8.
Most of your target list is on a long weekend right now. That's the point. Messages sent Tuesday morning land in inboxes that spent four days not accumulating the usual volume. H2 headcount unlocks at most growth-stage companies within two weeks. Both MOVE targets below are in their sharpest action window of the summer. Send Tuesday.
MOVE — Ramp, Director Product Design
What changed: Director, Product Design posted June 8. Twenty-five days live. Still actionable but approaching the zone where internal referral pipelines start to fill the slate.
Why it matters: Ramp's co-CEO Eric Glyman has publicly framed AI as reshaping "company strategy, technology, systems design, and every function's operating model." That framing tells you what this Director role actually governs: how AI decisions flow through financial workflows where errors cost money. Your "Trust Is the New Interface" essay and the five-handoffs framework were built for exactly this problem. Lead with agentic AI.
One thing worth noticing: no VP Design or Head of Design appears on Ramp's public leadership page, careers page, or LinkedIn presence. This Director role may report into product leadership, not a design chain. That changes the room you'd walk into. File it. Don't raise it in outreach.
Confidence: Moderate (posting confirmed via Ashby; no design hiring manager publicly identified; Eric is founder-level, not verified as search owner). Window: 7–10 days before the posting crosses into stale territory. July 8 is well-timed.
Move:
(a) Who: Eric Glyman, Co-Founder and Co-CEO (LinkedIn). Tenure: co-founded Ramp, so he's been there since inception. His public positioning treats systems design decisions as company strategy decisions. He recently took the co-CEO title alongside Karim Atiyeh, with Rahul Sengottuvelu stepping into CTO after leading Applied AI. That reshuffle puts AI at the C-suite level, not buried in a team.
(b) Warm path: Cold. No public mutual connection identified.
(c) Opening message (cold):
"Eric — your framing that systems design decisions are company strategy decisions is exactly the problem I've spent the last year working on. I published a framework in June ('Trust Is the New Interface') that maps the five handoffs where agentic systems either earn or lose user trust, and I've been shipping against it at Agentic Labs — including Carrier IQ, an InsurTech product where agent autonomy thresholds carry real cost if you get them wrong. I'd welcome a conversation about the Director, Product Design role and how that framework applies to what Ramp is building. Would next week work?"
(d) What not to say: Don't lead with Alibaba or enterprise scale. Ramp's culture language emphasizes speed, ownership, and shipping simple solutions. Anything that sounds like "I led a large org through a transformation" will pattern-match to slow. You need to sound like someone whose default mode dissolves constraints into the product rather than layering process on top.
Flag Ramp as a Battlecard candidate. If you send Tuesday, you'll need the deep context within days.
MOVE — Headway, Design Director Provider Experience
What changed: Design Director, Provider Experience posted June 4. Twenty-nine days live. The posting describes the provider EHR as "the operating system for mental health providers," with one session touching six distinct workflows: scheduling, telehealth, clinical documentation, outcome measurement, insurance verification, and billing.
Why it matters: CEO Andrew Adams has publicly stated that "humans plus AI will outperform either alone" and that Headway accelerated AI investment through the Tezi team acquisition. He spent six months focused on what AI could change for providers and patients before making that move. This is a company entering its complexity phase while layering AI into regulated workflows. Your Red Cross work (six systems consolidated to one, national deployment, $847K disbursed) and Thermo Fisher build (pharma supply chain from zero, 100% adoption, $20M+ margin) are the exact proof pattern. Both demonstrate designing compliance into the product so it accelerates the workflow rather than gating it. Lead with 0→1 high-stakes build.
Confidence: Moderate (posting confirmed via Ashby with detailed role language; Andrew Adams is founder/CEO, not verified as direct hiring manager; a VP Design or Head of Design likely owns this search but isn't publicly identified). Window: Narrow. At 29 days, this posting is at the edge. July 8 is the move.
Move:
(a) Who: Andrew Adams, Founder and CEO (LinkedIn). Tenure: founded Headway. His public statements focus on the fragmented connective tissue among patients, providers, and payers. His LinkedIn profile explicitly invites outreach about open roles. Founder-CEO outreach has a different register than hired-executive outreach: he built the mission, so the message should connect to the problem, not the org chart.
(b) Warm path: Cold. No public mutual connection identified.
(c) Opening message (cold):
"Andrew — the Provider Experience posting describes a problem I've solved twice in high-stakes regulated contexts: consolidating fragmented workflows into a single operating surface while layering in new capabilities without breaking trust. At the American Red Cross, I took six disconnected disaster-relief systems down to one and deployed it nationally ($847K disbursed through the redesigned flow). At Thermo Fisher, I built mySupply from zero for pharma supply chain — 100% adoption across six partners, $20M+ in margin. Both required designing compliance into the product so it accelerated the workflow rather than gating it. I'd welcome a conversation about how that pattern applies to what you're building for providers. Is there a good time next week?"
(d) What not to say: Don't lead with the agentic AI pillar. The posting's AI language is additive — "AI-enabled," "copilot" — describing a capability layer on top of the regulated workflow engine. Headway wants someone who builds that engine and integrates AI into it. Your agentic AI work is a secondary asset here, not the opener. Also critical: Headway's Core Insurance & Design Systems posting is a different role entirely. It's been live since October 2025, making it stale under any reasonable freshness model. Don't conflate the two.
Flag Headway as a Battlecard candidate.
PROBE — Capital One, Director Product Design in AI Experience Design
What changed: Posted May 28. Thirty-six days live. Daniela Jorge, SVP and CDO, arrived at Capital One from PayPal. This role follows her arrival and is tied to AI tooling, design-process evolution, AI-centric talent upskilling, and player-coach AI use across Design.
Why probe, not move: The posting language sits at the intersection of two very different mandates. One version: owning AI design governance with structural authority over standards, tooling, launch blocks, and decision rights. The other: evangelizing AI adoption internally with no launch block and no decision rights. Only the governance version is a real leadership role. The evangelism version is a change-management assignment wearing a Director title. Daniela is new enough that the mandate may not be fully defined yet, which means the probe could shape it.
What the probe should test: Does this role own the standards that determine whether an AI-driven experience ships or doesn't? Who holds the launch block? If the answer is product management or engineering, the role is influence without authority.
Confidence: Moderate (posting confirmed live as of June 30; Daniela's LinkedIn verified at Capital One, but no recent public statements from her about design transformation priorities were found in open sources. Her detailed activity is either gated or minimal, which is itself worth noting about how early this transformation is). Window: Narrowing. At 36 days, this posting is either closing its first candidate slate or has already failed once and is reconsidering. Probe within 1–2 weeks.
Move:
(a) Who: Daniela Jorge, SVP and CDO (LinkedIn). Tenure: recent arrival from PayPal. RIT-educated. No public design-transformation statements found, which suggests she's still in listening mode or building internal consensus before going public with a vision. That early window is when a probe carries the most weight.
(b) Warm path: Cold. No public mutual connection identified.
(c) Opening message (cold):
"Daniela — I noticed the Director, Product Design – AI in Experience Design posting and I'm curious about the mandate's shape. I've been working on the design governance question for agentic systems — where agent autonomy ends and user control begins — and published a framework on it in June. Before exploring the role formally, I'd value a brief conversation about how the AI design function is being structured under your leadership. Would fifteen minutes work?"
(d) What not to say: Don't position yourself as an AI evangelist. Capital One's company-level AI activity (ACL/ICML research, agentic systems workshops with University of Maryland) signals serious technical investment. The organization already believes in AI. Nobody has settled who governs its design yet. If the conversation reveals the role is evangelism, that's your answer.
Probe technique details are in the Probe Playbook sidebar.
WATCH
Suno — Head of Product Design posting still listed but published April 21. Seventy-three days old and stale. No fresh design leadership signal. Ian Oliver is listed as Design Leader on suno.com/about; no public warm path identified. Trigger: A fresh design leadership posting appears or is reposted, or you privately confirm a mutual connection to Ian or Suno's product leadership.
Gusto — No new design leadership signal this cycle. Trigger: A VP Design or Head of Design departure, or a cluster of two or more mid-level product design postings within two weeks.
OpenAI — No design leadership posting. Trigger: A public hiring post from a design leader, or a design leadership role on their careers page. Your agentic AI pillar and "Trust Is the New Interface" essay are pre-positioned.
Anthropic — No design leadership posting. Trigger: Same as OpenAI. Anthropic's safety-first positioning makes the trust-ladder framework an unusually strong match, but without a live role, outreach has no anchor.
RETIRE — Kiddom
Remove from the active list. No design leadership posting found on Lever. No signal of design org investment at the level you're targeting. Revisit only if a funding round or executive design hire surfaces. The preparation time belongs on Ramp and Headway this week.
Send Ramp and Headway messages Tuesday morning, July 8. Deploy the Capital One probe by July 15. Next scan: July 10, 2026.
- Ramp's missing design chain: No VP Design or Head of Design surfaces on Ramp's public leadership, careers, or LinkedIn pages, which means the Director role's reporting line is unresolved and worth asking about if you get a conversation.
- Headway's AI hiring cluster: Beyond Provider Experience, Headway posted Staff Product Manager, AI Platform on June 17 and Staff PM, AI Patient Experience on June 24, signaling that AI investment is accelerating across both provider and patient surfaces simultaneously.
- Suno's creator-trust controversy: The Verge reported on June 28 that Suno's new Spark incubator program drew criticism for its license terms, class-action waiver, and non-disparagement clause, which makes the trust-governance angle more relevant if a fresh design role appears.
- Capital One's AI research posture: Capital One's LinkedIn page shows active participation in ACL/ICML research and an agentic systems workshop with the University of Maryland, confirming that AI investment is institutional, not exploratory, which raises the stakes on whether Daniela's design mandate carries matching authority.