Founding Engineer

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.