Principal Product Designer, User Engagement

Upstart

87d • $198,700 - $275,000

About The Position

As a Principal Product Designer, User Engagement, you’ll shape how customers experience Upstart beyond their initial transaction. You’ll design the systems, tools, and touchpoints that deepen trust, promote financial wellness, and keep users coming back. This role sits at the intersection of vision and execution, blending craft, strategy, and cross-functional leadership to create compelling, habit-forming experiences that drive retention, loyalty, and lifetime value. You’ll collaborate closely with partners in Product, Engineering, Data Science, and Marketing to reimagine what engagement means across Upstart’s platform. You’ll champion elegant, intuitive design solutions informed by behavioral insights and business goals, balancing experimentation with a long-term vision for a cohesive, differentiated customer experience.

Requirements

• 10+ years designing and shipping high-quality digital products, with a track record of driving measurable impact on user engagement and retention.
• 2+ years designing for growth, engagement, or post-acquisition experiences in consumer products.
• A portfolio that demonstrates exceptional product thinking, behavioral insight, and end-to-end execution across multiple platforms.
• Deep experience with experimentation, A/B testing, and data-informed design iteration.
• Strong collaboration skills with a proven ability to influence senior product and engineering partners.
• Proficiency in Figma and research tools (e.g., UserTesting, Maze, Dovetail) and fluency in UX and visual systems design.
• Ability to translate complex user needs and business goals into clear, elegant, and scalable design solutions.
• Experience mentoring and guiding design talent to elevate craft, strategy, and cross-functional impact.

Nice To Haves

• Experience designing for consumer fintech or other regulated industries.
• Background in lifecycle design, growth experimentation, or marketplace ecosystems.
• Demonstrated success designing for engagement, retention, or cross-sell experiences in multi-product environments.
• Experience working within and contributing to design systems at scale.
• Deep commitment to accessibility, inclusive design, and ethical user engagement principles.

Responsibilities

• Design and deliver the vision for engagement across Upstart’s ecosystem, building experiences, from financial tools to personalized insights, that keep users returning and pave the path to upsell and cross-sell.
• Champion the user journey, crafting intuitive and rewarding experiences that build trust and increase lifetime value.
• Drive experimentation at scale, using rapid iteration and clear metrics to test what works.
• Lead with influence, collaborating across product lines and teams to stitch together a cohesive experience across our suite of offerings.
• Balance vision and execution, making strategic trade-offs across short-term optimization and long-term differentiation.

Benefits

• Competitive Compensation (base + bonus & equity)
• Comprehensive medical, dental, and vision coverage with Health Savings Account contributions from Upstart
• 401(k) with 100% company match up to $4,500 and immediate vesting and after-tax savings
• Employee Stock Purchase Plan (ESPP)
• Life and disability insurance
• Generous holiday, vacation, sick and safety leave
• Supportive parental, family care, and military leave programs
• Annual wellness, technology & ergonomic reimbursement programs
• Social activities including team events and onsites, all-company updates, employee resource groups (ERGs), and other interest groups such as book clubs, fitness, investing, and volunteering
• Catered lunches + snacks & drinks when working in offices

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 1,001-5,000 employees