What you bring

• 6+ years of product design, with a strong portfolio of shipped work.
• 2+ years designing LLM-powered products that are live with real users. Agents, assistants, or copilots. Not just concepts.
• You've written prompts and system instructions that shipped. You know how a small wording change moves behavior.
• You're comfortable in the weeds. You can read a trace, spot where an agent went wrong, and say why.
• You think in systems. You can design a pattern once and make it work across ten agents.
• You write clearly and plainly. In an agent product, the copy is the product.
• You've done research with people who aren't tech-first, and you respect how they work.
• You prototype in code. HTML, CSS, and JavaScript, or React Native, with help from AI tools like Claude Code. You use prototypes to test behavior against the real model, not just screens.
• You stay close to the models. You know what the latest ones can and can't do, and you design for where they're going, not where they were six months ago.
• Your craft is strong. Your UI is polished, clear, and builds trust.
• You've owned complex products end to end in messy, undefined spaces, and shipped anyway.
• You're happy in a small, fast team where the problem isn't fully defined yet.

About Sidekick Labs

Sidekick Labs is our AI agent team that is focused on making our agents trustworthy for the pros who use them, and for the teams who build them.

We have three jobs:

1. Build a platform other teams can build on. Any pod at Topline Pro should be able to ship an agent without us holding their hand.
2. Build a conversational experience Pros trust. Every agent should feel like one Sidekick. Pros stay in control while Sidekick does the work.
3. Build agents we're confident in. Every agent completes real tasks correctly, and we can prove it.

🏠 About Topline Pro

We're building an AI-powered Shopify for service businesses. We help service pros (e.g., roofers, landscapers, painters, cleaners) acquire direct business, fast. Up and running within minutes using Gen AI, our digital storefront products help pros get discovered, trusted, and booked repeatedly.

Topline Pro was co-founded by Nick Ornitz (CEO) and Shannon Kay (COO), with an excellent team of 120+ rockstars and plans to expand further in 2026. We serve thousands of local service businesses and were named one of the top 50 Tech Companies building for SMBs in 2023 and 2024.

We're YC-backed and well-funded, with several years of runway, and we've experienced rapid growth over the past year. We're in a phenomenal position to scale, with the financial foundation, product-market fit, and momentum to go big. You'll be joining at an inflection point, where the groundwork is laid, and the path to massive impact is clear.

We believe "great candidates" do not come about simply from a check mark next to past experience. We believe in hiring people, not just skills. Even if you do not check every box but find excitement at the prospect of working with us in this capacity, please apply.

Topline Pro is committed to building an inclusive workplace and assembling a team from diverse backgrounds. We ensure that individuals with disabilities receive reasonable accommodation throughout the application and interview process. We strongly encourage applications from underrepresented candidates and those from nontraditional backgrounds.