# Sydney L.

> Sr. Product Designer at Oportun

Location: New York, New York, United States
Profile: https://flows.cv/sydneyl

Portfolio: www.sydneyplee.com

Product designer with 7+ years leading 0-to-1 design across fintech and consumer platforms. Turns complex systems and sensitive data flows into trustworthy, human-centered experiences. Known for defining design direction, influencing roadmaps, and elevating team craft through experimentation, AI tooling, and cross-functional leadership.

## Work Experience
### Senior Product Designer @ Oportun
Jan 2023 – Present | New York, New York, United States
Leading product design across the Onboarding & Activation and Lending teams. Own e2e UX across a multi product mobile app spanning growth experimentation, core feature delivery, design systems, and AI-powered content tooling.

Beyond execution, I focus heavily on DesignOps, creating processes/frameworks that help the team deliver high quality work faster.

### Senior Product Designer @ Ambient
Jan 2023 – Jan 2023 | New York, New York, United States
Designed 0-1 experiences for an early-stage AI executive intelligence platform.

• Operated as the sole designer and established the product's foundational design system - component architecture, interaction patterns, and vis language across the product
• Designed core dashboard experience, balancing information density with scannability for time constrained executive users
• Created action item widget - metadata structure, bulk action interactions, add/export flow patterns to support high volume task management
• Designed meeting summary web templates and defined the interaction model for AI generated meeting intelligence outputs
• Built e2e integration flows for third-party tool connectivity (Jira, Notion, etc.)
• Designed upsell and upgrade flows, connecting in product moments to conversion

### Senior Product Designer @ Toucan (JoinToucan.com)
Jan 2022 – Jan 2023 | New York, New York, United States
Monetization design lead at a browser-based language learning platform, acquired by Babbel in 2023.

• Increased subscription conversion by +6.27% by redesigning checkout and paywall flows. 
• Established DesignOps and critique processes across product squads, standardizing design to eng workflows
• Collaborated with product and engineering leadership on roadmap prioritization and GTM strategy for new subscription tiers
• Provided mentorship to mid-level designers

### Senior Product Designer @ Deloitte Digital
Jan 2021 – Jan 2022 | New York, New York, United States
Delivered complex, compliance-heavy products at scale across a portfolio of federal, state and consumer clients (incl. Pfizer, IRS, FDA, NIH, Dept. Health & Human Services, WI Dept. of Health, Dept. of Defense)

• Translated technically complex workflows into structured, accessible interfaces for 2 clients serving 1.2M+ users
• Co-built a design system from scratch alongside visual designers; authored DesignOps documentation standardizing workflows across project teams
• Led UX research on 2 engagements - defined research plans, facilitated usability testing, and synthesized findings into artifacts that influenced product direction
• Designed health agency experience that contributed to securing a $100M follow on contract
• Delivered WCAG / Section 508-compliant responsive web, iOS, and Android designs
• Provided design direction and mentorship to junior designers across client teams

### Product Designer @ Deloitte Digital
Jan 2019 – Jan 2021 | New York, New York, United States

### Product Designer @ Sweeten
Jan 2019 – Jan 2019 | New York, New York, United States
Redesigned core product experiences including onboarding, contractor and renovator dashboards, and payments flows. Contributed to and maintained DOMO, Sweeten's design system. Established user research infrastructure from the ground up building processes for planning, facilitating, and synthesizing usability studies.

### Product Designer @ PeopleJoy
Jan 2019 – Jan 2019 | New York, New York, United States
Brief freelance role. Designed 0-to-1 onboarding flows for an early stage fintech startup. Created user research plans, facilitated sessions, and synthesized findings into design recommendations. Led ideation workshops and informed design strategy through competitive analysis, partnering directly with the CTO and Head of Product.

### Marketing Designer @ Cowtan & Tout
Jan 2018 – Jan 2019 | New York, New York, United States
Managed e2e creative production and marketing strategy for a luxury interior textiles brand. It was an early foundation in user-centered communication, content design, and business strategy that directly shaped my approach to product design.

• Designed marketing collateral and wrote copy for campaigns, press materials, and events
• Cultivated editorial partnerships with major design and lifestyle publications (AD, Vogue, ELLE Decor, Veranda) 
• Managed vendor relationships, production timelines, and campaign performance analysis

### Advertising Sales Associate, ELLE Decor @ Hearst
Jan 2016 – Jan 2017 | New York, New York, United States

### Sales & Marketing @ The New York Times
Jan 2014 – Jan 2014

### Finance Intern @ Committee for Economic Development
Jan 2010 – Jan 2010 | Washington D.C. Metro Area


## Education
### Bachelor of Science - BS in Marketing, International Business
Santa Clara University Leavey School of Business

### Certificate in The Science of Well-Being
Yale University

### Washington in DC
Georgetown Visitation


## Contact & Social
- LinkedIn: https://linkedin.com/in/sydneyplee
- Portfolio: https://www.sydneyplee.com/

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Source: https://flows.cv/sydneyl
JSON Resume: https://flows.cv/sydneyl/resume.json
Last updated: 2026-03-29