Senior Agent Designer

The role

You will design how the Sidekick AI agent thinks, behaves, and acts. You will work on conversation design, agent behavior, and creating reusable design patterns for agent behavior.

What you will do

• Design how Sidekick thinks, behaves, and acts
• Write prompts and rubrics that define good responses
• Lead the audit and set patterns for Sidekick across app, web, and partner surfaces
• Design the handoff from conversation to editable work artifacts
• Design how Sidekick explains its actions to build trust
• Design the waiting experience for complex requests
• Figure out how Sidekick teaches pros what it can do
• Define tone, error recovery, and confirmation rules through prompts and system rules
• Define response rubrics and work with engineering on automated checks
• Create reusable agent design patterns and help shape the Sidekick Labs roadmap

Required qualifications

• 6+ years of product design
• Strong portfolio of shipped work
• 2+ years designing LLM-powered products that are live with real users
• Experience writing prompts and system instructions that shipped
• Ability to read a trace and identify where an agent went wrong
• Ability to design patterns that work across multiple agents
• Clear and plain writing skills
• Experience doing research with people who are not tech-first
• Prototype in code using HTML, CSS, JavaScript, or React Native
• Knowledge of what the latest models can and cannot do
• Strong UI craft
• Experience owning complex products end to end in undefined spaces

About the company

Topline Pro is building an AI-powered Shopify for service businesses to help pros acquire direct business. Sidekick Labs is their AI agent team focused on making agents trustworthy for pros and builders.