Principal Software Engineer, Applied AI
Highspot
What You'll Do
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Design and build agentic AI systems that orchestrate multi-step workflows across heterogeneous enterprise content – documents, CRM data, analytics, and more – to deliver contextual, actionable answers for sales teams.
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Own the AI platform architecture – define the patterns, abstractions, and guardrails that enable multiple engineering teams to ship AI-powered features safely and independently.
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Build evaluation and observability infrastructure for non-deterministic systems – including automated regression testing, LLM-as-judge pipelines, and production quality monitoring – so the team can ship AI features with confidence.
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Drive model strategy and cost efficiency – evaluate and route across model providers, optimize context windows, and make principled latency/quality/cost tradeoffs at enterprise scale.
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Raise the AI engineering bar across the organization – not just within your team, but across engineering. Coach engineers on applied AI best practices, build shared tooling, and cultivate a culture where AI fluency is widespread.
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Drive operational excellence – ensure enterprise-grade reliability, security, and performance for all AI-powered features in production.
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Communicate complex technical concepts clearly to both technical and non-technical audiences, and translate business needs into actionable engineering investments.
Your Background
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Demonstrated depth in shipping production agentic AI systems – you've built multi-step, tool-using agents that operate on real data at scale.
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Deep expertise in context engineering: retrieval pipelines, ranking, prompt orchestration, and the tradeoffs involved in assembling context for LLMs over large, diverse document corpora.
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Hands-on experience building evaluation frameworks for non-deterministic AI systems – you understand why this is hard and have opinions on what works (synthetic evals, human-in-the-loop, LLM-as-judge, production monitoring).
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Track record of designing systems that balance quality, latency, and cost – including experience with model selection, routing, and optimization across providers.
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Strong instinct for platform thinking: you know how to build abstractions that accelerate other teams without over-constraining them.
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8+ years of professional software engineering experience, with significant time spent on distributed, data-intensive production systems.
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Strong programming skills in Python, Java, TypeScript, or equivalent. You're comfortable across the stack.
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Experience developing and operating cloud services at enterprise scale (AWS, Azure, or GCP).
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A track record of full product lifecycle ownership – from technical design through iterative shipping to production operation.
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Experience mentoring engineers and building collaborative, high-performing teams.
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Strong cross-functional collaboration skills — you work effectively with ML researchers, data scientists, product managers, and business stakeholders with different backgrounds and priorities.
What will set you apart:
Foundations:
This listing was aggregated from a public company job board. ResuBuild is not the employer. Always review the original posting before applying.
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