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.