Senior Prompt Engineering Jobs in Oregon (NOW HIRING)

We are seeking a Senior Prompt Designer II to define the overarching prompt architecture strategy, roadmaps, and governance frameworks powering BOLD's consumer-facing career tools. This is a senior leadership position for someone with genuine depth in prompt systems design, model behavior, and cross-functional enablement. You will build the system others work within, establishing frameworks, governance, and quality standards that ensure AI-generated content is consistent, human-sounding, and maintainable at scale. 

About this team

As Senior Prompt Designer II, you will sit at the intersection of long-term architectural vision, organizational mentorship, and rigorous data-driven design. You will support Content, Engineering, Data, and Product teams; acting as the expert who bridges creative intent and technical execution, while leading the professionalization of the prompt management function itself. 

What you'll do 

• Lead prompt framework design and strategy - defining end-to-end architecture, version control, CI/CD pipelines, and deployment playbooks for distributed teams.
• Design complex, high-impact prompt systems including multi-agent and chain-of-thought architectures for resume builder flows across global product lines.
• Partner with Engineering, Product, and Data to align prompt strategies with model selection, API cost reduction, performance budgets, and roadmaps.
• Architect evaluation frameworks and safety guardrails to benchmark LLM outputs globally, minimizing hallucination, bias, and AI-sounding content.
• Act as the cross-functional prompt design resource; translating requirements from Content, Engineering, Data, Product, and portal teams into production-grade implementations.
• Spearhead R&D into emerging AI paradigms, evaluate new models and tooling, and provide clear adoption recommendations.
• Mentor the prompt management team and contribute to building the function - structures, processes, documentation, and quality standards.

What you'll need

• 8+ years of professional experience with AI/ML systems, language technologies, or software product engineering.
• 4-5 years in prompt design or LLM product development, with a track record of shipping consumer-facing features at scale.
• Mastery of advanced prompt design paradigms: RAG, multi-agent architectures, chain-of-thought, context window management, and model behaviour trade-offs.
• Hands-on experience across LLM providers (OpenAI, Anthropic, Google) with clear understanding of behavioural differences and trade-offs.
• Experience designing and maintaining LLM evaluation pipelines (LLM-as-judge, human eval, automated metrics) and prompt versioning workflows.
• Strong instinct for naturalness, recognising and eliminating AI-sounding, repetitive, or generic output.
• Demonstrated ability to influence cross-functional roadmaps and mentor prompt designers or AI content teams.

What's good to have 

• Experience with resume builder products, HR tech, or career content platforms
• Familiarity with fine-tuning, RLHF, or preference data collection workflows
• Experience with structured output validation (JSON Schema, Pydantic, or equivalent)
• Familiarity with orchestration tooling: LangChain, LlamaIndex, LangSmith, PromptLayer, or equivalents
• Contributions to open-source prompt design projects or published writing on the topic

Benefits

Outstanding Compensation

• Competitive salary
• Bi-annual bonus
• 401(k) plan with match
• Equity in company
• Flexible spending accounts (health, dependent care)
• Internet and home office reimbursement

100% Full Health Benefits

• Medical, dental, and vision (optional plans for your family)
• Life & long-term disability insurance (optional)
• Mental health support and resources
• Wellness reimbursement (gym, health apps, etc.)
• Pet Insurance (optional)

Flexible Time Away

• Flexible PTO
• Sick time policy
• Observed holidays

Eligibility

Eligible Hiring Locations

This position is 100% remote, work from home.

BOLD can hire full-time residents of the following U.S. States & Territories: Arizona, California, Colorado, Connecticut, Florida, Georgia, Illinois, Indiana, Kentucky, Maine, Maryland, Massachusetts, New Hampshire, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Puerto Rico, South Carolina, Tennessee, Texas, Utah, Virginia, Washington, and Wisconsin.

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