About
The designer behind the screens people trust
Whether it’s by advancing telehealth access, advocating for your data privacy, or going 0-1 on a high-impact initiative, I design for the good of the people.
Josh Cheriyan
Seattle / Remote
Who I am
Open to lead roles
I’m Josh Cheriyan, a lead product designer based in Seattle. I’ve been designing since 2007 and working in UX and product since 2017, across healthcare, supply chain, data privacy, fintech and enterprise SaaS. I’ve spent that time learning how to hear and advocate for the people using the apps I design, while carrying real business outcomes as a partner to product and engineering.
Currently
Sidecar Health
Lead Product Designer · Member Experience & AI Enablement
Software now makes decisions about people’s health and their money.
Most of those decisions reach people on screens they don’t trust: a surprise bill, a form that asks for an ICD-10 code, a count done by hand.
I design the screens where that trust gets earned, and I measure whether it did.
Before UX
Never could I have predicted it.
A nerdy kid, nose deep in every novel he could get his hands on, signed up for a newspaper writing class his sophomore year of high school. That led to two years as sports editor, then a year as layout editor of the college paper and three as its chief editor, managing teams of up to 25 and putting out a 16-page print edition.
Journalism gave me photography, content writing, print layout and people management. I lived on studio and sports photography for a few years before enough was enough. Design kept rearing its head, and it was finally time to own it. I threw myself into freelance and agency work and grew from print into digital-first design.
Every design piece had me question its use, how people would interact with it, its business objectives, and what iterations would make it better. That became the undercurrent of my UX career. I studied to be a pastor, too, and spent years in clergy roles on the weekends; they made me a better designer, photographer and manager of people.
Obsessive attention to detail
Happy-path product design isn't for me. I want to see points of failure, consider less-traveled paths, and produce accessible-first design.
Pushing pixels with the best of them
I was a visual designer, newspaper editor and photographer as I learned my way into UX. Being a creative is in my bones: modern design, high-quality mockups, and form married to function.
You ≠ user
I don't build on assumptions. Customer interviews, usability tests, session replays, analytics, A/B tests, surveys, reviews and competitor analyses each give me another vantage point to test a hypothesis against.
Positioning
Healthcare, AI and data, designed and built
Ten-plus years of end-to-end product design across healthcare, supply chain, data privacy, fintech and enterprise SaaS. Today I lead design for member experience and AI enablement at a health insurance company rebuilding how cost savings reach members.
The numbers I'm proudest of: a billing transparency project that collected $4.5M in outstanding balances, a weight-care screener that lifted conversion 50%, a one-day LLM prototype that took first place out of 20+ teams and became PlushCare's AI self-service booking, and five zero-to-one AI products behind a $27M Series A with zero customer churn.
I've often worked without a dedicated PM, so I write the requirements and decision rules as well as the screens. I prototype in React and TypeScript with real APIs and AI tooling, then check the prototype against production so design intent survives the trip.
Career arc
Career arc
- 2026–PresentSidecar HealthLead Product Designer, Member Experience & AI EnablementHealth insurance · Series DLeading design across the pre-member and member apps: an overhaul of prescription shopping with a new pharmacy benefit manager, a brand refresh with product at the centre, and a novel cost-savings model that modernises care shopping.
- 2025–2026Clarium HealthSenior Product Designer, AI & Data5 zero-to-one products · $27M Series A · zero churn · 2x revenueLed design and product strategy across AI-powered hospital supply chain, usually without a dedicated PM: computer vision and LLMs that capture supplies in the operating room and cut waste, item intelligence for purchase orders, substitutions and recalls, vendor and contract resiliency scoring, a unified cross-product home, automated ERP data onboarding, a supplier portal, and real-time data reconciliation.
- 2022–2025Accolade / PlushCareSenior Product Designer, Consumer Growth UX Lead$4.5M collected · 1st of 20+ hackathon teams · 4.9 starsLed end-to-end patient experience for a $110M ARR telehealth platform serving 14M+ members across 1,000+ enterprise customers: billing redesign, onboarding, insurance and payment funnels, weight-management booking, Stripe payments with wallets and BNPL, and an LLM booking prototype that took first place out of 20+ teams at the company hackathon. Grew from one pod to four teams, and stepped into the PM seat three times.
- 2021–2022T3 CustomUX DesignerFintech agency · data-intensive web applicationsHired to design a financial analysis product while also designing marketing collateral and websites for major fintech clients, turning data-heavy workflows into scalable interfaces.
- 2017–2021Allytics + Integris SoftwareUX Designer → Lead Product Designer (contracted)Integris acquired by OneTrust · AWS · Microsoft · Milliman · RivianHired onto the creative team for marketing collateral, then contracted to Integris for a few years as the sole designer of its data privacy product until it sold to its leading competitor, OneTrust. In the same years I designed AWS Partner TV, Rivian's post-purchase confirmation and insurance flow (fall 2020), a Milliman product microsite in a 10,000-page migration, Microsoft Surface launch work, and SaaS for Datacore, 47Lining and Buurst.
- 2007–2017City of Kent · Designer Portrait Studio · The Discourse BrandGraphic Designer · Lead Photographer · Freelance Designer~500 city projects · 60+ sports programs · Included.ai · SanMarGraphic design at the City of Kent's internal agency: around 500 marketing, web and print projects for financial, economic development and citizen-facing departments. Before that, lead photographer for sports leagues around Washington, scheduling up to twenty contractors and designing for 60+ programs, and a freelance practice in web, print, photography and video, including zero-to-one discovery for a DEI e-learning product.
How I partner
How I partner
With product
I meet each PM I work with weekly, co-run kickoffs and design sprints, and sit in engineering standups. I've stepped into the PM seat three times: when a role was cut, when a PM left mid-project, and while a PM was on parental leave for a quarter.
With engineering
Discovery, design, then scoping: a PRD and an epic with the context, the metrics we're driving, universal requirements, stakeholders and a target release. Then handoff, QA and a launch behind a feature flag or an A/B test, watched closely in the first week before it opens up.
With everyone else
Customer success, operations, clinical and data science all use the product and all have ideas about it. I bring them into brainstorms and sizing, because discovery shouldn't feel off-limits to the people closest to the user.
How I work
How I work
- Design it twiceAfter layoffs left me as the only designer on a product, I designed every project twice: once in the production UI, and once in a north-star visual direction. The new UI came into the product a piece at a time, and the org could always see where it was headed.
- Hang every project on the journeyI tie each project to a point on one shared user-journey bar, with the goal of eventually covering the main flows for a few key personas. Every project shows where it sits in the whole.
- Build the system while shippingOn a product with a decade of legacy UX, I built a basic component library underneath the features I was already shipping, so the system grew with the work.
- Leave the reasoning in the fileI keep sticky notes in Figma next to the decisions they explain, so a reviewer can follow why a screen looks the way it does without me in the room.
- Carry the PM work when there's no PMAt an early-stage startup I framed problems, wrote requirements and decision rules, defined workflow states and prioritized the first release. Design and product definition were one job, and I treated them that way.
- Get it out of SlackWhat I wrote after an onsite design sprint: sometimes getting issues out of Slack and into real life speeds things up quite a bit.
- Close the gap to productionI prototype with AI in working code, then reconcile the drift between the prototype and the production front end, so what was reviewed is what ships.
Principles
What the work taught me, in the words I wrote at the time.
A price you can see is part of the care.
The interface was never the form. It was the question.
Chronic care is designed in the gaps between visits.
Trust is the first requirement I write down.
Accessible first, intuitive second, beautiful third, all tightly knit.
Earn the right to have an opinion.
Skills & approach
Skills and approach
Design
- End-to-end product design
- Interaction and visual design
- Design systems and tokens
- Information architecture
- Web, iOS and Android
- Accessibility and inclusive design
Research & strategy
- User research and usability testing
- A/B testing and data-informed design
- Journey mapping and user flows
- Competitive analysis
- Product strategy and roadmaps
- Requirements and decision rules, as acting PM
- Healthcare data modeling and taxonomy
- Executive communication
AI & prototyping
- Designing for AI/ML-native products
- LLM and computer vision interfaces
- AI prototyping: Claude, Lovable, v0, Cursor
- React / TypeScript prototyping
- Figma: variables, dev mode, components
- AI-assisted research workflows
- Prototype-to-production drift checks
Where I’ve worked
Startups, scale-ups and some of the largest platforms in the world.
- Clarium
- Accolade
- PlushCare
- Amazon Web Services
- OneTrust
- Integris Software
- Rivian
- Microsoft Surface
- Milliman
- Sidecar Health
- T3 Custom
- Dell
- Google Cloud
- Microsoft Azure
Mentoring · since 2026
Founding mentor on a design mentorship platform.
I joined a new design mentorship platform as one of its founding mentors in mid-2026. I run intro chats and deep-dive 1:1 sessions with early-career designers, present at mentor show-and-tells, and gave the founder product feedback in the platform's first weeks.
Questions
What recruiters and hiring managers ask me first.
The work behind all of this