Software Developer

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🕒 May 26

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Guideline

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2015

💸 Finance

☁️ SaaS

🤝 B2B

💰 $200M Series E - Guideline on 2021-06

Finance • SaaS • B2B

Guideline is a provider of employer retirement plan services and online platform that delivers automated 401(k) plan administration, recordkeeping, and guided investment portfolios. It offers investment advisory services through Guideline Investments, an SEC-registered adviser, and integrates tightly with payroll systems (notably Gusto) to automate deductions, contributions, compliance, and reporting. The company targets employers with a self-serve SaaS portal and B2B offerings to simplify retirement benefits for small and mid-sized businesses.

📋 Description

• Design and ship multi-step AI agents using modern orchestration frameworks (Claude, OpenAI Agents SDK, or equivalent), including prompt design, state management, tool calling, and human-in-the-loop control. • Build and maintain MCP servers and tool integrations connecting agents to internal services, data warehouses, and third-party APIs; define clean schemas, error handling, and least-privilege authorization scopes. • Implement retrieval-augmented generation (RAG) pipelines — ingestion, chunking, embedding, hybrid retrieval, reranking — grounded in Guideline’s proprietary spend, pricing, and media datasets. • Develop offline and online evaluations (LLM-as-judge, deterministic checks, golden sets, regression suites) that measure agent quality, tool-use correctness, task completion, latency, and cost before each release. • Instrument agents with end-to-end tracing and observability (e.g., OpenTelemetry, LangSmith, MLflow) and operate them in production: monitor drift, regressions, prompt-injection attempts, and hallucination rates. • Apply security and safety controls — input/output filtering, prompt-injection defenses, sandboxed tool execution, PII handling, data residency — in collaboration with Security and Compliance. • Optimize for cost and latency through model routing, caching, batching, and choosing the right level of agency — deterministic workflow vs. autonomous agent — for each problem. • Write production-quality Python with strong testing discipline; contribute to backend services, APIs, and CI/CD pipelines that host agent workloads. • Partner with product, data science, and design to translate ambiguous business problems into well-scoped agent specifications, success metrics, and rollout plans. • Stay current on the rapidly evolving agent ecosystem and bring back patterns the team should adopt — or reject — with a clear rationale.

🎯 Requirements

• 3+ years of professional software engineering experience shipping production systems, with at least 1 year focused on LLM-powered or agentic applications. • Strong Python skills, including async programming, type hints, testing, and clean API design. Comfort with Git-based development and modern CI/CD. • Hands-on experience with one or more agent frameworks (LangGraph, LangChain, OpenAI Agents SDK, Anthropic SDK, CrewAI, AutoGen, Pydantic AI) and provider APIs from at least one of OpenAI, Anthropic, or Google. • Practical experience with the Model Context Protocol (MCP) or equivalent tool-protocol patterns; ability to design clean tool interfaces and reason about authorization scopes. • Demonstrated experience building RAG systems, including vector stores (e.g., pgvector, Pinecone, Weaviate), embedding selection, hybrid search, and reranking. • Working knowledge of agent evaluation: designing evals, building golden sets, running LLM-as-judge, and interpreting results to make ship/no-ship decisions. • Familiarity with prompt engineering tradecraft and an empirical mindset — preferring measurement over intuition for agent behavior. • Solid grasp of cloud infrastructure (AWS, GCP, or Azure), containers (Docker), and at least one production runtime — Kubernetes, serverless, or comparable. • Understanding of LLM security and safety: prompt injection, data exfiltration, output validation, sandboxing, and least-privilege tool access. • Strong written and verbal communication; ability to write design docs, present trade-offs, and collaborate across product, data, and security functions.

🏖️ Benefits

• Health, dental, life, and disability insurance • RRSP with company match • Paid time off and parental leave • Teledoc Health services • Employee recognition and referral bonuses