Phase 1 — The Moment
Headway posted Staff Product Designer, Group Practices on September 3. The mandate underneath the title: scale a supervisory billing pilot from two states to fifty, designing the permissions architecture that keeps administrators, supervisors, provisionally licensed supervisees, and patients each inside their regulatory lane. Those lanes shift at every state line, payer contract, and license type.
The posting is one day old, but the more consequential signal is Ellen Dong's departure. Dong left Headway after 4.5 years to become Head of Design at eldercare startup Hera. No replacement announced. LinkedIn timestamps put her exit in late August (her post appeared roughly five days before this brief, and she said she'd joined Hera two weeks prior), but the exact date can't be confirmed from public signal. Verify in the first conversation. The Issue #8 battlecard mapped Dong as the function-level evaluator and Roland Tiangco as the provider-scope route. First half of that mapping is void. Tiangco remains as Director of Provider Product Design, though his formal hiring authority for this req is unconfirmed.
A hiring committee without its design executive makes decisions by consensus and over-indexes on candidates who can operate without supervision. That window closes the day a new Head of Design arrives and starts picking their own reports.
Company 8 / Role 12 — Watch by threshold, Act by timing. The Dong vacancy creates a temporary advantage the rubric can't capture: a committee without its design executive over-indexes on autonomous operators, and your Thermo Fisher and TinyFish track records are that proof.
| Dimension | Score | Basis |
|---|---|---|
| AI centrality (bonus) | +1 | Tezi acquisition adds AI engineering; posting says "AI-first." Product is a provider network, not an AI product. |
| Stage & equity window | 2 | Series D, $2.3B, 773 days old. Meaningful equity but window narrowing. |
| Design influence ceiling | 2 | 30+ person team with domain leads. Head of Design vacancy makes ceiling temporarily unreadable. |
| Trajectory | 3 | 75K+ providers, Tezi acquisition, supervisory billing expansion, 11 design hires in 4 months. |
| Total comp | 2 | Staff at $2.3B. Posted range $212K–$265K plus equity. Top of range clears $250K; actual offer depends on leveling. Equity upside moderate given the 773-day-old round. |
| Scope expandability | 3 | "Only segment-based pod." Owns full lifecycle. Supervisory billing scaling from 2 to 50 states. |
| Craft depth | 3 | Design anchor. Hands-on IC with strategic influence on the pod. |
| AI exposure quality | 2 | AI-adjacent via Tezi and posting language. Not core AI product work. |
| Portfolio value | 2 | Regulated multi-party workflow is strong proof. Not a frontier AI case study. |
Phase 2 — Portfolio Mapping
Positioning archetype: Healthcare/Regulated. Thermo Fisher leads.
Lead with Thermo Fisher. Headway's supervisory billing has the same multi-party regulatory architecture you designed through at Thermo Fisher. Supervisor-to-supervisee ratios vary by state. Co-signature requirements create clinical approval chains. Administrator permissions deliberately exclude clinical actions so the billing holds up legally. Thermo Fisher's mySupply was six pharma partners across nine sites in three regulatory jurisdictions, each with its own compliance gates, approval workflows, and data-visibility rules. $20M+ margin recovered, 100% partner adoption, 12 months. The questions are the same across both: who sees what, who approves what, and where the regulatory boundaries fall.
Support with Allē. The dual-surface structure maps cleanly. Administrators see payments and rates; providers working in Sigmund Lite, Headway's practice tool, see only their own calendars and clients. Allē's 30M members and 40K+ provider practices required the same split — different interfaces, different data visibility — and produced a 3.2× redemption rate without collapsing either side into the other.
Carrier IQ adds AI credibility. The posting says "AI-first" and Headway acquired Tezi's AI team five months ago. Carrier IQ is regulated industry plus agentic automation: insurance quote workflows running under compliance constraints. It signals you've designed agent-mediated work where the regulatory constraints are fixed, not negotiable.
TinyFish: most recent role context. Shipped an AI-native enterprise platform 0→1 in three months. That establishes technical currency and matches the pace this role demands.
The objection. Why is a Head of Product applying for a Staff Product Designer role? The screener flags this before a human engages, which makes it a screening problem rather than an interview problem. Your answer: you moved to product to build AI-natively from zero, and you shipped it. You returned to design to apply that depth to a regulated domain. Thermo Fisher and Allē demonstrate the level you actually work at; TinyFish shows you chose to go deeper technically, not that you stepped down. Preempt this in the cover letter's fourth sentence, not the closing paragraph.
Competitive landscape. Healthcare design specialists from Oscar, Talkspace, or similar (moderate confidence) will outperform you on domain familiarity and underperform on regulated multi-party workflow at Thermo Fisher's jurisdictional complexity. Growth-stage platform designers (moderate confidence) understand organizational permissions but haven't worked inside clinical-regulatory constraints. Internal candidates (speculative) bring institutional context; whether any of them has 0-to-1 scaling experience is unknowable from outside.
Phase 3 — The Outreach Package
Warm path: your connection graph to Tiangco and Poses isn't visible from public signal. Treat this as cold outreach unless you find mutuals. If you do, put them in the close, not the opening.
Target: Roland Tiangco, Director of Provider Product Design. His public record is thin, so the posting's own language is the hook.
First Contact Message
Subject: Supervisory billing permissions across 50 regulatory jurisdictions
Roland — the Group Practices posting caught me because of the supervisory billing mandate. Scaling a multi-party clinical workflow from a two-state pilot to fifty states, where each state defines supervision ratios, license categories, and co-signature requirements differently, is a problem I've solved in a different regulated domain.
As Product Design Director at BCG Digital Ventures, I led Thermo Fisher's mySupply platform: six pharma partners across nine sites in three regulatory jurisdictions, each with different compliance gates and approval chains. We shipped in 12 months, recovered $20M+ in margin, and hit 100% partner adoption. The permissions architecture underneath that — who sees what, who approves what, where the lane lines fall — is the same architecture Group Practices needs for administrators, supervisors, and supervisees.
I'd value 20 minutes on how you're thinking about the state-by-state scaling challenge.
Cover Letter
The hardest design problem in Headway's Group Practices product is the permissions architecture underneath the interface: an administrator who manages the business cannot co-sign a clinical note, a provisionally licensed supervisee who treats the patient cannot see the practice's financials, and the rules governing who sees what change at every state line.
I designed through that exact structure at Thermo Fisher, where six pharma partners across three regulatory jurisdictions each required different compliance gates, approval workflows, and data-visibility boundaries, and the platform had to enforce all of them without making anyone's daily work feel like a compliance form. As Product Design Director at BCG Digital Ventures, I led mySupply from zero to launch in 12 months: $20M+ in margin recovered annually, 100% partner adoption across nine sites, 83% IRR.
I've also designed both sides of a provider/consumer platform. At Allergan's Allē loyalty program (Product Design Director, BCG Digital Ventures), 30M members and 40K+ provider practices needed different interfaces, different data visibility, and different success metrics; we drove 3.2× redemption rates by designing for both audiences rather than compromising between them. Most recently as Head of Product at TinyFish, I shipped an AI-native enterprise platform from 0 to 1 in three months. I've returned to design to apply that technical depth to a specific regulated domain, which is why this role rather than a broader one.
I'd welcome the chance to discuss how the state-by-state scaling challenge maps to what I built at Thermo Fisher. My portfolio is at junochen.com.
Resume Emphasis Guidance
- Lead with Thermo Fisher mySupply — $20M+ margin, 6 pharma partners, 9 sites, 100% adoption, 12 months. Frame it as regulated multi-party permissions design. Product Design Director at BCG Digital Ventures.
- Follow with Allē — 30M members, 40K+ practices, dual-surface, 3.2× redemption. Product Design Director at BCG Digital Ventures. Frame as provider/consumer platform design.
- Third: Agentic Labs Carrier IQ. Regulated industry plus agentic automation. This is what answers the "AI-first" language in the posting.
- TinyFish in the header as bridge: "Most recently, Head of Product at TinyFish (enterprise web agent platform, Series A). Shipped agentic platform 0→1 in 3 months."
- Subordinate Alibaba. Enterprise scale still counts, but regulated multi-party workflow counts more here than marketplace GMV.
- Trim Red Cross and Equinox+ unless space allows. Neither maps as precisely.
- Avoid leading the summary with the "Head of Design" framing from Alibaba. Lead with "Product Design Director" to match the craft-depth signal this posting is screening for.
Post-outreach signals: growth-stage platform timeline. Response within 3–5 business days is normal. Silence past 7 days, one follow-up at day 8 with a new signal hook. No reply after that, close the loop and redirect. If a recruiter screen gets scheduled on first contact, the search is moving fast; prioritize prep the same day.
Phase 4 — Window Summary
| Action | Deadline | What degrades without it |
|---|---|---|
| Send first contact to Tiangco | September 8 | Posting will be 5 days old. A design org without its head reads early applicants more carefully, because there's no one to filter the pile down first. |
| Check LinkedIn for mutual connections to Tiangco and Poses | Before sending | A warm introduction moves the message from application to referral. |
| Ask about reporting structure in the first conversation | First screen, no later than September 15 | The Head of Design vacancy means this role's scope depends on who fills that seat. If a hire is already identified internally, the window may close before an offer. |
- Headway's other Provider role: The Senior/Staff Product Designer — Provider posting covers credentialing, clinical documentation, and agentic billing automation, and says designers use Claude Code and Cursor to prototype through launch.
- Jenna Leonardo's patient-side scope: Leonardo's personal site identifies her as leading design for Headway's patient and insurance groups, which means the provider-side reporting line likely runs through Tiangco or directly through Poses, not through her.
- Dong's design-sprint practice as interview prep: Before leaving, Dong described an AI-enabled design-sprint model where senior designers led domain sprints and used Magic Patterns to produce interactive blueprints — worth understanding whether this practice survived her departure and shapes the interview loop.
- Tezi acquisition timeline: Headway acquired the Tezi AI team in March, bringing VP of Engineering Raghavendra Prabhu into the product org — ask in conversation how that team's work connects to Group Practices and whether AI-assisted clinical workflows are on the near-term roadmap for this pod.