Head of Design — Candidate Work · AI-Native Financial Services

Design that
earns trust
in complex systems.

Here are seven case studies from AI-native financial data platforms, enterprise wealth management, and personal End-to-End design projects. The work lives in the hard part — where compliance meets usability, and where the humans operating these systems spend their actual day.

7
Case Studies
7+
Years designing
Both
IT + business users
AI-first
Design approach
Case Study 01
AI Transformation Builder
ROLE: Lead Designer
SCOPE: Product + Interaction
View Full Case Study ↗
The Problem
Business analysts need to build data transformations — but can't write SQL.
Financial firms rely on engineering teams to build and maintain every data pipeline, leaving business analysts — the people who actually understand the data — waiting weeks for even small changes. The challenge: design an AI-assisted interface that lets non-technical users confidently review, adjust, and approve AI-generated outputs without needing to understand what's happening under the hood.
Primary User
Business Analyst
Secondary User
Data Engineer
Core Challenge
Non-deterministic AI output in a compliance-sensitive context
Design Insight
"Confidence alone isn't enough. Users need to know what the AI is uncertain about — not just how uncertain it is."
Solution — AI Transformation Builder
Nexus — AI Transformation Builder
INTEGRATIONS
Dashboard
Sources
Transformations
3
Pipelines
Audit Log
2
Destinations
Settings
fx_rates → trades_normalized
bloomberg_feed · Last run: 14:02:31 · 4,821 records
● LIVE
1,204 runs
▸ AI TRANSFORM PROMPT
Normalize trade_date to ISO 8601 and join on fund_id where currency = USD
Generated SQL
Previous versions
Diff view
-- AI-generated · Review before accepting
SELECT
  t.fund_id,
  t.trade_date::DATE AS trade_date_iso, ⚠ casting assumed
  t.amount,
  t.currency,
  f.fund_name,
  f.custodian_id
FROM trades t
JOIN funds f ON t.fund_id = f.id
WHERE
  t.currency = 'USD'
  AND t.trade_date IS NOT NULL;
   
-- Estimated rows: 4,821 of 5,200 (92%)
AI CONFIDENCE
91% · verify DATE cast on line 4
✓ Accept
✎ Edit
✕ Reject
Case Study 02
Compliance Monitoring Dashboard
ROLE: Lead Designer
SCOPE: Product + Data Viz
View Full Case Study ↗
The Problem
Compliance officers can't tell what the AI touched — and regulators are asking.
When AI is involved in processing financial data, every action it takes needs to be visible, traceable, and easy to explain to regulators. Compliance officers — who aren't technical — need to quickly distinguish what the AI did from what humans or automated systems did, and access the full record of any action with minimal friction.
Primary User
Compliance Officer
Regulatory Context
SEC, FINRA audit readiness
Core Challenge
Dense data must be scannable by non-technical users under time pressure
Design Insight
"Audit logs fail not because they lack information — but because they're designed for the system, not the auditor. Start with the questions regulators actually ask."
Solution — Compliance Monitoring Dashboard
Nexus Compliance — Q4 2024 · Waterfront Capital Advisors
INTEGRATION COMPLIANCE MONITOR
Waterfront Capital Advisors
Q2
Q3
Q4 2024
YTD
Total Events
24,817
↑ 12% vs Q3
AI Actions
3,104
12.5% of total
Flagged for Review
47
↑ 3 unresolved
Schema Exceptions
2
Requires action
Timestamp
Event
Integration
Actor
Status
Records
14:02:34
Schema validation failed — v2.1 mismatch, pipeline halted
custodian_feed
system
CRITICAL
0
14:02:33
AI inferred ISIN from CUSIP — field absent in source
custodian_feed
ai-agent
AI ACTION
3,104
14:02:31
Trade date normalized to ISO 8601 · accepted by user
bloomberg_feed
r.foss
VERIFIED
4,821
13:58:10
Scheduled FX rate refresh · USD/EUR, USD/GBP
fx_rates
system
SUCCESS
182
13:44:02
AI transform edited by user before acceptance
bloomberg_feed
j.chen
MODIFIED
4,821
13:30:00
Daily pipeline triggered · all sources synced
all
scheduler
SUCCESS
9,808
Product Design 01 · Full-Stack App
Market Matchup
ROLE: Solo Designer + Developer
STACK: React · Node · SQLite
View Full Case Study ↗ Launch App ↗
The Idea
Make stock trading feel like fantasy sports.
Learning to invest is intimidating, and tracking stock prices is hard to care about until something's at stake. Market Matchup turns it into a competition — players start with the same simulated budget, build real portfolios using live market data, and race to grow it the most. No real money, no fear barrier — just a genuinely engaging way to learn how markets work.
Type
Fantasy investing competition
Data
Finnhub live market API · 30s refresh
Result
+27% return · #1 finish in live league
Design Insight
"Fantasy sports proved that real-world data becomes compelling when there's a competitive social layer. The same principle scales to investing — and removes the fear barrier completely."
Solution — Live Fantasy Investing Platform
Market MatchUp — Dashboard Market Open · Closes in 4h 12m
SELECT LEAGUE
Total Portfolio Value
$135,404.73
↑ $35,404.73  ·  +35.40% total
Cash Available
$19,718.35
Invested
$115,686.38
League Rank
#1
of 3 players
League
Bro Vs. Bro
3 members
Status
ENDED
Feb 25, 2026
TOP HOLDINGS
SPY20 shares @ $756.11▲ $1.51$15,122.20+10.94%
GOOGL20 shares @ $382.73▼ $7.40$7,654.60+21.19%
GS10 shares @ $1,007.92▼ $0.45$10,079.20+23.64%
🏆 OVERALL STANDINGS
#1
R
Ryza
$135,404.73
+35.40%
+$35,404
#2
T
Tim
$100,000.00
+0.00%
#3
S
Sean Towne
$98,278.70
-1.72%
📅 THIS WEEK'S PERFORMANCE
👑 Ryza Week Leader
+0.00%
$127,669.33 → $127,669.33
🏅 Winner gets a badge on Sunday!
Case Study 03 · Featured
Equity Event Management
PLATFORM: Private Equity Admin
SCOPE: Complex Workflow UX
View Full Case Study ↗
The Problem
Startup founders spend hours every funding round reconciling cap tables — across tools that were never designed to talk to each other.
Equity events — option grants, secondary sales, convertible notes — are processed across DocuSign, 409A platforms, and spreadsheets with no single system tracking the chain of cause and effect. The cap table isn't wrong because data is lost. It's wrong because there's no sequence, no shared visibility between founders and legal counsel, and no compliance signal until after an event is already executed.
Primary User
Startup Founder
Secondary User
Legal Counsel
Platform
Private Equity Admin · Startup Tooling
Design Insight
"The design problem was integration and sequence, not data entry. A consistent state machine means founders and legal counsel build a shared vocabulary once — they don't re-learn it for every event type."
Solution — Unified Equity Events Queue
Equity Platform · Equity Events · app.equityplatform.com/events
Open events
18
↑ 4 this round
Compliance risk
2
409A stale flags
Awaiting legal
5
Pending signature
Executed this qtr
11
Cap table current
Event / recipient
Type
Status
Age
Option grant — M. Chen (Series B)
#EQ-20814 · 48,000 options · $2.40 strike
Option Grant
409A Stale
12d ⚠
Convertible note — Horizon Ventures
#EQ-20798 · $500K · 6% interest
Convertible Note
Awaiting Legal
7d
Secondary sale — J. Okafor to Arclight
#EQ-20841 · 12,000 shares · $8.15/sh
Secondary Sale
In Review
4d
Option grant — R. Patel (new hire)
#EQ-20857 · 20,000 options · 4yr vest
Option Grant
In Progress
2d
SAFE conversion — Seedstage Fund II
#EQ-20790 · $1.2M · cap table updated
SAFE
Executed
9d
Additional Work — Fintech, Enterprise & Personal Projects
More UX / UI & product design
CASE 04 · REGULATORY UX
KYC Digital Onboarding
Reduced corporate client drop-off 60% by redesigning KYC as a journey, not a compliance wall. Live AML screening, document preview.
View Case Study →
PD 02 · CITY MATCHING APP
LIVE
Cititype
61-question lifestyle survey that matches users to their ideal US city. Top-10 ranked results with 5-dimension scores, housing links, city guides. Firebase auth. Full-stack.
View Case Study →
PD 03 · IMAGE CONVERTER
FREE
ASCII Art Studio Pro
Drop any image — get professional ASCII art instantly. 5 conversion modes, 8 fine-grain controls, 9 export formats including Python, SVG, and ANSI terminal. Zero dependencies.
View Case Study →
About the designer
Ryan Foss
HEAD OF DESIGN CANDIDATE  ·  DERRY, NH

I design the interfaces that matter when the stakes are high — AI-generated SQL that compliance officers have to trust, adverse event windows that clinical coordinators can't miss, case queues where three wrong prioritizations mean a regulatory breach. Seven years in medical device manufacturing taught me how regulated industries actually work. A BFA in graphic design and a decade of freelance product work gave me the rest.

My engineering background lets me sit in architecture discussions and ship prototypes that work exactly like the real thing. My work spans AI interaction patterns, data-dense enterprise UX, compliance tooling, design systems, and full-stack implementation.

I'm targeting Lead Product Designer and Head of Design roles at biotech, pharma, medical device, and AI-native fintech in Boston, San Diego, or remote. I want to own a design system from tokens to production.

7+
Years designing
7
Projects & cases
0→1
Systems built
Ryan Foss at Top of the Rock, New York City
Ryan Foss
Designer · Builder · Problem Solver
AI Product Design
Non-deterministic outputs, streaming interfaces, confidence signals, and human-AI control handoffs. Trust is the design problem.
NL → Code UX Confidence Signals Accept/Edit/Reject AI Audit Design
Enterprise UX
Data-dense interfaces for IT and business users in the same product. Compliance tooling, audit logs, role-based views — built for the 8-hour workday.
B2B / Enterprise Compliance UX Dense Data Tables Financial Services
Design Systems
Tokens before components. Built 0→1 systems that engineering adopts voluntarily. Figma variables, Dev Mode handoff, semantic color, spacing scales.
Figma Expert 0→1 Systems Token Architecture Dev Handoff
Full-Stack Context
Enough engineering to participate in architecture discussions and ship production-fidelity prototypes. Python, Flask, React, HTML/CSS/JS, SQL.
React / JS Flask / Python HTML / CSS SQL
CAD & Technical
7 years in CAD detailing at a medical device manufacturer. GD&T, engineering drawings, PLM systems. The rare designer who reads engineering specs.
CAD Detailing Medical Devices GD&T PLM / SofTech
Visual Design
BFA from Plymouth State. Typography, brand, print, animation, illustration. Brings editorial sensibility to enterprise interfaces that usually have none.
Graphic Design Typography Brand Identity Animation
"Design is not the last mile.
It's the whole road."