Senior Prompt Designer 2
About the job
- At least 8 years of professional experience with AI/ML systems, language technologies, or software product engineering.
- 4–5 years of experience in prompt design or LLM product development, with a track record of shipping consumer-facing features at scale.
- Mastery of advanced prompt design paradigms, including retrieval-augmented generation, multi-agent architectures, chain-of-thought, context window management, and model behavior trade-offs.
- Hands-on experience across LLM providers including OpenAI, Anthropic, and Google, with an understanding of their behavioral differences and trade-offs.
- Experience designing and maintaining LLM evaluation pipelines, including LLM-as-judge, human evaluation, automated metrics, and prompt versioning workflows.
- Ability to recognize and eliminate AI-sounding, repetitive, or generic output.
- Demonstrated ability to influence cross-functional roadmaps and mentor prompt designers or AI content teams.
- Define end-to-end prompt framework architecture and strategy, including version control, CI/CD pipelines, and deployment playbooks for distributed teams.
- Design complex prompt systems, including multi-agent and chain-of-thought architectures, for resume builder flows across global product lines.
- Partner with Engineering, Product, and Data teams 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 and minimize hallucination, bias, and AI-sounding content.
- Translate requirements from Content, Engineering, Data, Product, and portal teams into production-grade prompt implementations as a cross-functional resource.
- Research emerging AI paradigms, evaluate new models and tooling, and provide adoption recommendations.
- Mentor the prompt management team and help build the function's structures, processes, documentation, and quality standards.
- Experience with resume builder products, HR technology, or career content platforms.
- Familiarity with fine-tuning, RLHF, or preference data collection workflows.
- Experience with structured output validation, such as JSON Schema or Pydantic.
- Familiarity with orchestration tools such as LangChain, LlamaIndex, LangSmith, or PromptLayer.
- Contributions to open-source prompt design projects or published writing on the topic.
About the company
BOLD helps job seekers improve their careers by providing online tools, guidance, and support. Its core products include AI-powered resume and cover letter builders and job search tools that assist users in creating strong application documents and finding opportunities. The resume/cover letter builders use artificial intelligence to generate tailored documents based on user input, while job search tools help users discover roles, track applications, and optimize their job-hunting process. BOLD differentiates itself through a large global team across engineering, product, data science, design, and more, a track record of award-winning AI-driven tools, and a presence in over 180 countries, offering end-to-end career support from resume creation to job search. The company’s goal is to transform work lives by helping people achieve their career dreams.
Company Size
1,001-5,000
Company Stage
N/A
Total Funding
N/A
Headquarters
San Juan, Puerto Rico
Founded
2005
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Simplify's Take
What believers are saying
- BOLD acquired Joblist on May 26, 2026, adding 100 million-plus search behavior signals.
- BOLD completed CareerBuilder and Monster acquisition on July 31, 2025, expanding employer traffic reach.
- Sonara relaunched in June 2026, giving BOLD an AI job-search product under active monetization.
What critics are saying
- Rocket Resume sued BOLD on April 2, 2026 for monopolistic deception and anticompetitive conduct.
- BOLD’s subscription model faces cancellation scrutiny across resume sites; regulators can target pricing practices fast.
- If antitrust discovery exposes unified management and pricing, BOLD’s brand moat becomes a liability.
What makes BOLD unique
- BOLD aggregates Monster, CareerBuilder, FlexJobs, Joblist, and Sonara under one employer stack.
- BOLD owns dozens of resume brands, creating unusual distribution across job seeker touchpoints.
- BOLD’s AI resume and auto-apply products pair traffic, subscriptions, and application workflows.
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Benefits
Remote Work Options
Flexible Work Hours
Hybrid Work Options
Professional Development Budget
Conference Attendance Budget
Wellness Program
Mental Health Support
Phone/Internet Stipend
Home Office Stipend
Company News
Joblist, a job-search platform launched by Wilbur Labs in 2019, has been acquired by BOLD, a global career technology leader. The company has helped over 100 million people find jobs since its inception. Unlike traditional employer-focused platforms, Joblist was built to prioritise job seekers, offering customised recommendations and smart search technology. The platform accelerated its launch by six months during the pandemic, when the US lost over 22 million jobs, and rapidly expanded to Canada, the UK and Australia. Joblist later introduced Joblist Employer, a self-serve recruitment tool that has generated tens of thousands of applications. BOLD's portfolio includes MyPerfectResume, Monster, FlexJobs and CareerBuilder, alongside its AI platform Sonara.
BOLD has officially acquired the job board assets of CareerBuilder + Monster, expanding its portfolio with two of the most iconic brands in HR tech.
CareerBuilder + Monster has completed its sale transactions with BOLD, Iron Corp U.S. Inc., and PartnerOne. BOLD acquired the job board business, retaining the Monster and CareerBuilder brands, and offered jobs to 350 employees. Iron Corp U.S. Inc. acquired Monster Media Properties, while PartnerOne acquired Monster Government Solutions. These transactions conclude the company's Chapter 11 sale process, maximizing value and ensuring continuity for clients and employees.
Timeline, a Swiss biotech at the forefront of developing innovative solutions for healthy aging and longevity, today announces that it raised CHF 56M (USD 66M) in an oversubscribed Series D financing round. This marks a significant milestone for the company and includes strategic investments from two global industry leaders—L’Oréal and Nestlé.
Flexjobs.com the B2C remote job board community founded by Sara Sutton back in 2006 has been acquired by career company BOLD, which owns a number …