We are seeking a highly experienced Staff Engineer to join the Sidekick team.

The $100 billion residential real estate industry is powered by real estate agents and brokerages who are radically underserved by the existing, legacy software ecosystem. Sidekick, the leading generative AI assistant purpose built to help agents and brokerage drive efficiency and business growth, is creating a new category of transformative technology for real estate. Sidekick is backed by some of the world's leading investors including Cox Enterprises/Socium Ventures, Craft Ventures, Threshold Ventures, Zigg Capital, Good Friends, and 75 & Sunny.

As a key technical leader, you will be responsible for full-stack development across the Sidekick platform, including system design and architecture of large-scale, distributed systems.

You will work closely with cross-functional partners to design, engineer, and maintain products with core tenets of high performance, scalability, and operational excellence.

This is a high impact role that requires both strategic thinking and hands-on execution and will report directly to our CTO.

Responsibilities

Lead full-stack development, ensuring high-quality, scalable, and maintainable code.
Inform, design, and architect distributed systems that are highly scalable, reliable, and optimized for performance.
Drive technical leadership, collaborating with product managers, developers, and stakeholders to optimize project scope, timelines, and deliverables.
Implement and enforce best practices for system architecture, security, and operational efficiency, with a focus on monitoring, compliance, and cost optimization.
Mentor and guide engineering teams, providing technical direction, code reviews, and best practices to foster a high-performing development culture.
Collaborate with cloud engineering counterparts to hone continuous delivery, observability, and incident management, with a strong focus on operational excellence and system uptime.
Optimize systems for performance, scalability, and reliability while honing resource utilization across cloud environments and partner platforms.
Be a thought leader on the latest trends and industry standards, including adoption of new tools, technologies, and process improvements.

Required Qualifications

10+ years of experience, with at least 4 years in a senior, lead, or staff engineering role.
Leading engineering teams in startup environments from 0-1 onto hyper-growth.
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 microservices architectures, REST, GraphQL, and RPC.
Extensive experience in languages such as Typescript, Go, Python, Rust, and Scala.
Proficiency in front-end stacks such as React, Vue, and Tailwind.
Strong focus on operational excellence, with a track record of designing systems for reliability, scalability, and performance.
Excellent communication skills and ability to collaborate with cross-functional teams.
Demonstrated track record in mentoring, influencing, and leading engineering teams.

Preferred Qualifications

Experience developing AI centric products, data science, and machine learning systems.
Proficiency operating composable LLMs, model training, and fine-tuning.
Familiarity with AI platforms and tools, including proprietary and open-source offerings.

Selected Benefits

Key member of a small, tightly-knit team
Ground-floor equity in a fast-growing, high-potential startup
Medical, Dental, and Vision Benefits
401k program available
Unlimited vacation days
Flexible work environment (remote or in-person, depending on location)

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