Founding Engineer

## About the Role Sidekick is hiring a Founding Engineer to join the core team. The real estate industry is undergoing a massive shift, and AI is about to reshape how millions of agents operate daily. Sidekick is first to market with a verticalized solution, has strong early traction, and is backed by leaders who've built and sold category-defining products. We're building the AI-powered operating system for residential real estate agents to streamline workflows, boost productivity, and unlock new growth opportunities. Sidekick combines advanced large language models with deeply integrated domain-specific tools to handle the complexity of real estate—from data to transaction management and daily operations. We've hit product-market fit and are growing rapidly. Here's why now is a great time to join Sidekick: - Accelerating Product Market Fit: We're solving urgent, high-value problems for real estate professionals and have seen rapid adoption from top agents, brokerages and MLSs across the U.S. - Industry-Defining Partnerships: We're working hand-in-hand with some of the most forward-thinking brokerages and real estate leaders to shape the future of AI in the industry. - Elite, Cross-Functional Team: Our team includes seasoned operators, engineers, designers, with deep industry experience. - Generative AI, Purpose-Built: At Sidekick, engineers work directly with foundation model APIs and our own proprietary data pipelines to build AI-native workflows that reimagine how agents operate—from lead to close. - Compensation + Ownership: We offer competitive salary, generous equity, and the opportunity to make a foundational impact at an early-stage company with breakout momentum. This is a high impact role that requires both strategic thinking and hands-on execution, reporting directly to the CTO. ## Responsibilities You will develop and improve our AI systems, including: - Fine-tuning large language models on real estate-specific workflows and communications for workflows like listing description generation, client response drafting, task management, and lead follow-up. - Building evaluation frameworks to ensure high-quality and safe model outputs. - Designing and implementing novel search and question-answering algorithms over real estate data (e.g., listings, market trends, CRM activity). - Collecting, structuring, and indexing fragmented industry datasets from MLSs, brokerage platforms, and public sources to support agents with MLS search, pricing analysis, comp generation, and deal insights. - Building and orchestrating large systems of interconnected LLMs to power end- to-end agent workflows, solving challenging engineering problems around low-latency interactions, expensive model inference, and tool/model integration. ## Impact - Work directly with our CTO and founders. - Own technically challenging problems at the frontier of applied LLMs—like grounding generative output in proprietary real estate data, aligning agent-facing assistants with high recall, and minimizing latency under production load. - Inform, design, and architect distributed systems that are highly scalable, reliable, and optimized for performance. - Be a thought leader on the latest trends and industry standards, including adoption of new tools, technologies, and process improvements. ## Required Qualifications - Experience developing AI centric products, data science, and machine learning systems. - Proficiency operating composable LLMs, including model training and fine-tuning. - Familiarity with AI platforms and tools, including proprietary and open-source offerings. - Proven experience building and operating large-scale distributed systems. - Strong expertise in AWS, Google Cloud, or Azure cloud platforms. - Experience with CI/CD, infrastructure as code (IaC), and container orchestration. - Solid understanding of microservice architectures, REST, GraphQL, and RPC. - Extensive experience in languages such as Typescript, Go, Python, and Java. - Proficiency in front-end stacks such as React, Vue, and Tailwind. - Excellent communication skills and ability to collaborate with cross-functional teams. ## Select Benefits - Ground-floor equity in a fast-growing, high-potential startup. - Medical, Dental, and Vision. - 401k program. - Unlimited vacation days. - Flexible work environment. ## Location This is primarily a remote position. Sidekick is optimizing for hiring in the Bay Area.