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Pencil is an advertising technology SaaS company leveraging generative AI to redefine content creation. The company's mission is to democratize AI-powered advertising, making advanced tools accessible to small businesses and creative individuals alongside enterprise brands.
As a Product Designer for Brief Mode, you will own the end-to-end experience of how advertising briefs are created, understood, and brought to life within Pencil's platform. This spans from initial brief upload through AI analysis, collaborative editing, review and approval workflows, to final creative delivery. You will design at the intersection of agentic AI and real creative workflows, determining when AI suggests, when it acts autonomously, and how users maintain control throughout the process. Your designs will serve both global brand teams and two-person agencies with equal clarity and confidence.
Key responsibilities include:
- Owning the complete Brief Mode experience from discovery through delivery
- Designing agentic and AI-assisted interactions, prototyping rapidly in Figma and AI tools, and producing clear, build-ready handovers
- Collaborating closely with Product, Engineering, and AI teams; conducting user research and usability testing; leveraging product analytics and session replays to identify friction and validate design decisions with evidence
- Evolving and maintaining Pencil's design system with reusable patterns that work for both enterprise and self-serve users
Success is measured by: 5 active clients using the entire briefing flow by end of 2026; percentage increase in briefs submitted per active workspace; percentage of deliverables reaching final approval; and percentage of briefs where Brief Mode agents are initiated.
Requirements:
- 5+ years of product design experience on B2B SaaS or complex workflow tools, with a portfolio demonstrating end-to-end ownership of shipped features
- Hands-on experience designing AI-powered products (generative, conversational, or agentic interfaces), including handling uncertainty, loading, and error states
- Strong interaction and systems thinking: ability to design multi-step flows, permissions, statuses, and edge cases within coherent experiences
- Fluency in Figma and rapid prototyping; comfort with AI prototyping tools or front-end basics (React, component libraries) is a strong plus
- Experience using qualitative research and quantitative data (e.g., Amplitude) to shape and validate decisions
- Bonus: experience in adtech, marketing, creative operations, or agency workflows
