Juniper Square - Staff Software Engineer (AI)
Requirements
• 7+ years of backend and/or ML engineering experience with a trajectory of increasing technical leadership, architectural responsibility, and mentorship • A portfolio of shipped production systems - we will ask you to walk through specific technical decisions you personally made and code you personally wrote; this is not a role for someone whose primary contribution has been directing others • Deep expertise in Python, with strong proficiency in building production-grade backend services; experience with other server-side languages (Node/TS, Java) a plus • Production experience building and operating AI/LLM-powered systems — such as AI SDKs, RAG pipelines, evaluation frameworks, agentic workflows, or model observability — in real systems, not just experimentation • Experience leading technical design for complex systems, including making architecture decisions, evaluating tradeoffs, and guiding implementation across multiple engineers or teams • Experience with relational/NoSQL databases, including schema design, performance tuning, and data modeling • Experience building and operating cloud-native systems using AWS, Docker, Kubernetes, and infrastructure as code • Strong understanding of CI/CD, observability, reliability, and operational excellence in production environments • Ability to work through ambiguity, break down complex problems, and drive alignment across engineering, product, and design • Demonstrated ability to raise engineering quality through technical standards, design reviews, mentoring, and reusable platform patterns • Hands-on experience with AI-native development tools (e.g., Cursor, Augment); demonstrated ability to embed AI-driven practices to accelerate team velocity and code quality • Ability to critically evaluate AI-generated code and outputs, including identifying failure modes, regressions, and edge cases • Preferred • Experience with document processing pipelines, structured extraction, or vector stores • Familiarity with MLOps tooling, experiment tracking, or model deployment pipelines • Background in financial document processing or fintech data pipelines • Prior experience in a technical lead or TLM capacity on a new or early-stage product team
Responsibilities
• Own Technical Direction & Architecture • Set the technical direction and own the architecture for your domain's systems, from design through production • Lead technical design for ambiguous, cross-functional initiatives - evaluating tradeoffs, aligning stakeholders, and driving implementation • Be instrumental in your team's transition from monolith to service-oriented architecture • Evaluate and select technologies with a bias toward what ships well and scales sustainably • Build & Deliver • Write production code as a hands-on individual contributor - this is not a role that delegates implementation to others • Own end-to-end delivery of roadmap projects: design, coding, testing, and production • Manage your team's short-term roadmap (spanning the next two quarters), proactively surfacing execution, cost, and technical risks and driving pragmatic mitigation • Lead the development of complex, full-stack workflows, working across frontend and backend engineers • AI Fluency & AI-Native SDLC • Practice AI Fluency across the full software development lifecycle - deliberately choosing where AI versus traditional software is the right tool, and defending those tradeoffs against real criteria (latency, accuracy, cost, data sensitivity, explainability) • Champion and embed AI-native development practices and tools (e.g., Cursor, Augment) to drive significant productivity gains across your team • Adapt code review and testing practices for an AI-assisted SDLC - catching AI-specific failure modes (hallucinated dependencies, overconfident but incorrect logic) before they ship • Build and evaluate agentic workflows and AI-assisted systems where they add real value, with clear human-in-the-loop boundaries and monitoring for failure • Guard against over-reliance on AI tooling, in your own work and in the code you review, balancing velocity with system comprehension and accountability for outcomes • Foster a culture of rapid iteration, high velocity, and quality, and help raise AI fluency across the team • Lead & Grow the Team • Mentor engineers, raise the quality of technical decision-making, and help the team execute with consistency • Establish coding standards, review practices, and architectural documentation that scale as the team grows • Partner with recruiting to build and grow the team • Collaborate Cross-Functionally • Work closely with product, design, QA, and customer support to translate requirements into executable technical plans • Participate actively in design reviews and roadmap discussions with a grounded, implementation-level perspective • Handle most cross-team conflicts and technical decisions autonomously • Operational Excellence • Own monitoring, diagnosing, and resolving production issues within your team's services • Use observability tooling to measure and improve system performance and reliability • Implement and uphold best practices that maximize developer productivity across the team • Domain Expertise • Grow into a subject-matter expert in your domain, with an in-depth understanding of customer needs and the value your systems deliver
Benefits
• Compensation for this position includes a base salary, equity, and a variety of benefits. The U.S. base salary range for this role is $210,000 – $260,000 USD. Actual base salaries will be based on candidate-specific factors, including experience, skillset, and location, and local minimum pay requirements as applicable. • Health, dental, and vision care for you and your family • Life insurance • Mental wellness coverage • Fertility and growing family support • Flex Time Off in addition to company-paid holidays • Paid family leave, medical leave, and bereavement leave policies • Retirement saving plans • Allowance to customize your work and technology setup at home • Annual professional development stipend • Your recruiter can provide additional details about compensation and benefits.
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