Senior Software Engineer

We're looking for a results-oriented, self-motivated, and pragmatic Senior Software Engineer who is passionate about building highly scalable, user-friendly web applications and wants to see their work directly help small businesses grow. You'll be joining our Relationship/Retention team, where the focus is on deepening the value members get from their connections over time. This team builds the AI-assisted tools and workflows that help small business owners nurture relationships and turn them into referralsthink intelligent writing assistance, relationship management features, and follow-up experiences that keep members engaged and growing.

We are most importantly looking for someone to play a key role in shaping how AI-powered features are built and improved, designing systems that incorporate LLMs, defining evaluation strategies, and closing the loop between model output and real user behavior.

As a Senior Engineer on this team, you'll be a key technical voice: shaping how we build, influencing what we build, and raising the bar for quality across the team. You'll work closely with product management, design, and business partners from the earliest stages of problem identification through to production. You'll be expected to drive technical decisions with confidence, contribute meaningfully across the full stack, and help grow the engineers around you.

Responsibilities:

• You will take ownership of significant features from concept to production, collaborating closely with small cross-functional teams throughout.
• You will be a go-to technical voice on the team, contributing to architecture decisions, driving technical discussions, and proactively identifying risks and opportunities.
• You will be deeply involved in feature and technical decisions, using data to drive rapid testing and iteration.
• You will operate with a high degree of autonomy, working independently with product managers and designers to build the most compelling features for our small business members.
• You will design and iterate on LLM-powered features using structured evaluation frameworks.
• You will build feedback loops that continuously improve AI systems, leveraging user behavior, annotations, and experimentation to refine model outputs.
• You will contribute to the development of scalable LLM infrastructure.
• You will help define quality standards for AI outputs (accuracy, relevance, tone, safety) and ensure they are measurable and improving over time.
• You will get to know our members by listening in on video calls and training sessions, observing them using our site, and deeply engaging with our customer success team to understand their challenges.
• You will dive deep into our data to draw insights that inform feature suggestions and improvements to our applications.
• You will actively contribute to raising the technical bar of the team through code reviews, thoughtful feedback, and knowledge sharing.

Requirements:

• You have hands-on experience building or integrating LLM-powered features into production systems, including prompt engineering, retrieval pipelines, and agentic architectures.
• You have experience designing structured LLM evaluation frameworks and building feedback loops that improve model performance over time, not just shipping features but measuring and iterating on their quality.
• You have experience building and operating LLM infrastructure at scale, including observability, versioning, and reliability patterns.
• You have experience designing, developing, and deploying enterprise solutions using Amazon Web Services (AWS).
• You have a proven track record of owning complex features end-to-end and driving them to production with quality and speed.
• You have led architecture decisions and technical discussions and have…