[Hiring] Staff Software Engineer @Olly Olly

Role Description

We are seeking an experienced Staff Software Engineer to join our team and work on our app for small business owners. The app includes a suite of tools to help small businesses grow, such as lead management, review management, business listings, ads reporting, AI-generated content, and more. The ideal candidate will design, test, and implement this product, reporting to an Engineering Manager and in partnership with the Product team.

Utilizing their knowledge of programming languages and system design, the Staff Software Engineer will provide technical leadership to the engineering team members through each stage of our software development lifecycle including:

• Data structure and algorithms
• Architecture design
• Code review
• Troubleshooting and updates

What you'll do:

• Partner with your Engineering Manager and the Product team to define the scope and scale of projects
• Own the architecture of our AI content pipeline: what context each model receives, how tasks are broken into steps, and which model runs each step, balancing quality, cost and latency
• Build automated quality checks for AI-generated content that catch hallucinations before human review, using evaluation sets built from real data to measure the impact of every prompt change
• Develop, design, and maintain scalable web applications, mobile applications, and RESTful APIs
• Write clean, efficient, well-documented code, maintaining code quality and security
• Collaborate with cross-functional teams to design, develop, and deploy applications
• Troubleshoot and debug applications
• Identify bottlenecks and continually improve software efficiency
• Stay up-to-date with emerging trends and technologies in software development

Qualifications

• 7+ years building production software.
• You've taken a product or major feature from 0 to 1 and owned it after launch: live, measured and used. Ideally at a startup, or as a founder or lead.
• You learn new languages, frameworks and domains as the work requires, and you enjoy doing it.
• You have shipped a production feature built on LLM output and owned where it fails (hallucination, bad output, cost), not just the API integration.
• Deep experience with TypeScript and SQL/Postgres, building production software used by many people.
• You use AI coding agents, such as Claude Code or Cursor, daily on production work, and you own the quality of the code they write.
• You raise the bar for the team through code review, written standards and mentoring.
• You raise risks early, with options.

Requirements

• Supabase (Postgres and Deno Edge Functions).
• Google Cloud Functions and Pub/Sub.
• Flutter / Dart.
• Evaluating LLM output with rubrics or LLM-as-judge graders.
• Multi-step LLM generation with critic or validation passes.
• Retrieval or fact-checking pipelines.
• Generating local SEO or marketing copy.

Competencies

• Attention to Detail: Possess a strong sense of monitoring and checking information while organizing time and resources efficiently.
• Critical Thinking: Self-starter, solution-oriented and inquisitive mindset. Ability to think strategically and problem-solve. Values quality and organization.
• Problem-Solving: Ability to identify possible solutions to solve a problem or situation.
• Innovation: Strong commitment to continuous improvement.