Senior Agent Designer

Topline Pro•Boston, MA

18h

About The Position

The Senior Agent Designer will be the first designer dedicated to Sidekick Labs, shaping how Sidekick thinks, behaves, and acts across the app, web dashboard, and partner surfaces. The role covers the conversational experience and the transitions from conversation to usable outputs such as quotes, invoices, and posts; how Sidekick explains its work, handles delays and errors, and helps Pros discover its capabilities. The designer will define agent behavior, including tone, when to ask clarifying questions or act, error recovery, and customer-facing confirmations. They will write prompts and system rules, review conversation traces, define quality rubrics, label real conversations, and collaborate with engineering on automated evaluations. They will also create reusable agent-design patterns, develop new interaction conventions, and help shape the Sidekick Labs roadmap with product and engineering. Sidekick Labs focuses on building a platform other teams can use to ship agents, a consistent and trustworthy conversational experience that keeps Pros in control, and agents that complete real tasks correctly with measurable evidence. Topline Pro builds AI-powered storefront products that help local service businesses acquire direct business and get discovered, trusted, and booked.

Requirements

At least 6 years of product design experience and a strong portfolio of shipped work.
At least 2 years designing LLM-powered products, such as agents, assistants, or copilots, that are live with real users.
Experience writing prompts and system instructions that shipped, with an understanding of how wording changes affect behavior.
Ability to read agent traces, identify where an agent went wrong, and explain why.
Systems thinking and ability to make design patterns work across multiple agents.
Clear, plain-language writing.
Experience conducting research with people who are not tech-first and respect for how they work.
Ability to prototype in code, such as HTML, CSS, JavaScript, or React Native, using AI tools such as Claude Code; use prototypes to test behavior against real models.
Knowledge of current model capabilities and limitations, and ability to design with awareness of their direction.
Strong visual and interaction craft, including polished, clear UI that builds trust.
Experience owning complex products end to end in ambiguous environments and shipping them.
Comfort working in a small, fast-moving team where the problem is not fully defined.

Responsibilities

Audit Sidekick’s availability and experience across the app, web dashboard, and partner surfaces, and establish patterns for improving it.
Design the transition from conversation to real, editable work such as quotes, invoices, and posts.
Design how Sidekick shows and explains its work without overwhelming busy Pros.
Design waiting experiences for complex requests.
Help Pros discover Sidekick’s capabilities at relevant moments in conversation.
Define agent tone, clarifying-question and action behaviors, error recovery, and confirmation before customer-facing actions.
Write prompts and system rules that establish desired agent behavior.
Define quality rubrics, label real conversations, inspect traces, and collaborate with engineering on automated evaluations.
Create reusable agent-design patterns for other product teams.
Invent new conventions for agent interactions that feel clear and natural to Pros.
Help shape the Sidekick Labs roadmap with product management and engineering.
Prototype agent behavior in code and use prototypes to test against real models.