Lead Product Designer, Ads & Monetization

Job Title: Lead Product Designer, Ads & Monetization

Company: Upwork

Location: Remote – Chicago, IL

Job Type: Full-time

Compensation: $151,500 – $215,500/year

Overview:

Upwork is seeking a Lead Product Designer to shape monetization experiences within its marketplace. This role focuses on creating innovative advertising solutions, including promoted listings and sponsored placements, aimed at connecting businesses with top talent while optimizing platform revenue. You will work at the intersection of design, discovery, and performance, driving the strategy and execution of ad-focused user experiences.

Responsibilities:

• Lead design strategy for Ads & Monetization across web and mobile platforms
• Collaborate with cross-functional teams to align design with business goals and user needs
• Create intuitive, ethical ad experiences integrated into marketplace workflows
• Prototype and test new ad formats and placement strategies
• Use data and user research to optimize performance-driven features
• Build scalable design patterns and ensure visual and UX consistency
• Mentor peers and contribute to design culture and best practices

Qualifications:

• Experience designing monetization or advertising experiences (preferably in marketplace or search-driven environments)
• Strong product thinking and ability to align design with KPIs and growth goals
• A compelling portfolio showcasing monetization design and user-centered approach
• Proficient in Figma, prototyping, and experimentation frameworks
• Understanding of AI-powered systems or surfacing logic is a plus

Benefits Include:

• Comprehensive medical, dental, and vision insurance
• 401(k) plan with matching
• Employee Stock Purchase Plan
• Paid parental leave
• Unlimited PTO
• Tuition assistance