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.
California Residents: Please see our privacy notice for more info on how we handle your data.
SELECT ONE: #LI-Remote
Individual pay is based on location, transferable skills, experience, and other relevant factors. This estimated range is based on the best available market data and factors, all of which are subject to change. This position may also be eligible for a bonus and medical, dental, vision, life, short and long-term disability insurance, 401(k), paid time off, sick leave, and paid holidays, all subject to applicable plan terms.
About Bold
We Transform Work Lives
As an established global organization, BOLD helps people find jobs. Our story is one of growth, success, and professional fulfillment. We create digital products that have empowered millions of people in 180 countries to build stronger resumes, cover letters, and CVs. The result of our work helps people interview confidently, finding the right job in less time. Our employees are experts, learners, contributors, and creatives.
We Celebrate And Promote Diversity And Inclusion
We value our position as an Equal Opportunity Employer. We hire based on qualifications, merit, and our business needs. We don't discriminate regarding race, color, religion, gender, pregnancy, national origin or citizenship, ancestry, age, physical or mental disability, veteran status, sexual orientation, gender identity or expression, marital status, genetic information, or any other applicable characteristic protected by law.
Under San Francisco's Fair Chance Ordinance, qualified applicants with arrest and conviction records will be considered for the position.
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
