Bold Jobs Hiring Now
Bold is hiring for 9 open roles on Migrate Mate as of July 16, 2026, concentrated in software engineering and product management, with listed salaries up to about $225,000. Migrate Mate updates Bold's live openings daily. Bold is a technology and software company that builds career and productivity tools, including resume builders and job search products used by professionals across the U.S.
Find Bold JobsOverview
Bold hiring data on Migrate Mate, as of July 16, 2026.
- Open jobs
- 9
- Top team
- Software Engineering
- Seniority
- Manager level or above
- Work type
- 89% remote or hybrid
- Top location
- Chicago
- Salary range
- $110,000–$225,000
Listed salaries for Bold roles on Migrate Mate range from about $110,000 to $225,000 per year across 9 open roles, as of July 16, 2026. One role lists an hourly contract rate.
Open Roles at Bold
Showing 9 of 9+ Bold jobs
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
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.
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
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.
Job Roles at Bold
Working at Bold
Bold's 9 open roles are manager level or above, and about 89% are remote or hybrid. The most active teams are software engineering, product management, and growth marketing. Bold is a technology and software company focused on career tools and digital productivity products, with roles spanning product management, applied AI, engineering, and program operations. Most Bold roles are based in Chicago, with some in Guaynabo and Harrisburg.
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Browse jobs by roleBold Jobs: Frequently Asked Questions
How many jobs is Bold hiring for right now?
Bold is hiring for 9 open roles on Migrate Mate as of July 16, 2026, updated daily, concentrated in software engineering and product management. Roles span product management, AI engineering, program operations, and software development, ranging across seniority levels.
What kinds of roles does Bold hire for?
The most active teams are software engineering, product management, and growth marketing. Bold's open positions include product managers, applied AI engineers, browser automation engineers, senior prompt designers, and program specialists. Most postings are manager level or above, with a strong emphasis on product, engineering, and technical program roles across its software and career-tools business.
Are Bold jobs remote or in-person?
Mostly remote. About 89% of Bold's open roles on Migrate Mate are remote or hybrid as of July 16, 2026, with the rest based in Chicago. Each Bold listing shows its work location so you can filter before applying.
How do I apply to a job at Bold?
Find a role that fits your background among Bold's open listings on Migrate Mate, then follow the listing through to Bold's own careers page to submit your application directly. Bold manages its own hiring process, so all applications, interviews, and hiring decisions go through the company.
What do Bold jobs pay?
Listed salaries for Bold roles on Migrate Mate range from about $110,000 to $225,000 per year as of July 16, 2026, with most postings at manager level or above. One role lists an hourly contract rate. Exact pay is set by Bold and shown on each listing.
Does Bold hire entry-level?
Most of Bold's open roles on Migrate Mate are manager level or above as of July 16, 2026. Entry-level openings are limited. Check individual Bold listings for stated experience requirements.
Where is Bold hiring?
Most Bold roles are based in Chicago, with some in Guaynabo and Harrisburg, and about 89% offer remote or hybrid work as of July 16, 2026. Migrate Mate shows the location on each listing.