About Bobsled

Bobsled is building AI-powered analytics experiences that turn natural language into accurate, production-grade insights. Our mission is to enable enterprise customers to leverage the full power of AI and data agents, transforming how they access and act on their data. As we scale our AI product, we’re seeking hands-on specialists to ensure our customers’ deployments are robust, contextually tuned, and delivering measurable value.

What You’ll Do

Own the deployment, configuration, and ongoing management of Bobsled’s AI data agents for enterprise customers, acting as the primary technical point of contact for a small book of accounts.
Rapidly develop subject matter expertise in each customer’s data layer, context layer, and operational workflows.
Design, implement, and tune context ingestion, data pipeline integration, and agent orchestration to ensure high-performing, reliable AI deployments.
Write and ship production-grade code, customizing and extending Bobsled’s platform to meet customer-specific requirements.
Collaborate closely with customer stakeholders (technical and non-technical) to understand business objectives, untangle complex requirements, and translate them into actionable technical solutions.
Conduct rapid prototyping, iterative solution development, and high-touch troubleshooting directly in customer environments.
Monitor, evaluate, and improve the performance of deployed solutions, leveraging feedback loops to identify opportunities for enhancement and generalization.
Document best practices, reusable patterns, and deployment primitives, contributing to internal knowledge bases and future product abstractions.
Partner with Bobsled’s product and engineering teams to relay insights from the field, shaping platform evolution and customer success strategies

What We’re Looking For

4+ years of hands-on experience in data-focused engineering roles, such as analytics engineer, data analyst, or data engineer.
Proficiency in modern programming languages such as Python or TypeScript, with a strong willingness to work across the stack.
Demonstrated experience managing and integrating data layers (warehouses, pipelines, ETL, SQL) and context layers (semantic models, metadata, knowledge graphs) in enterprise settings.
Experience tuning and operating AI/LLM applications, including prompt engineering, retrieval-augmented generation (RAG), context management, and agent-based architectures.
Track record of working directly with customers to deliver technical solutions, including requirements gathering, solution design, and hands-on implementation.
Exceptional communication skills and customer empathy; able to translate between technical and business stakeholders, and build trust through high-touch engagement.
Bias for action, autonomy, and ownership; able to operate independently in ambiguous environments and drive projects to completion.

Nice to Have

Prior experience deploying AI/LLM systems or analytics platforms in enterprise environments.
Familiarity with context management and data agent orchestration in AI applications.
Experience with text-to-SQL systems and semantic layers.

Success Looks Like

Multiple enterprise customers successfully onboarded, with robust, high-performing Bobsled AI deployments tailored to their unique data and context layers.
Measurable improvements in agent performance and customer satisfaction, driven by your technical interventions.
Documented best practices and reusable deployment patterns that accelerate future customer implementations.
Short feedback cycles between customer deployments and Bobsled’s product/engineering teams, leading to rapid platform evolution and customer wins.

Compensation

Competitive salary and meaningful equity
Comprehensive benefits

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