WA

Weekday AI (YC W21)

Verified Job SourceRecruitment agency

Curated top jobs for you

Technology, Information and Internet
51–200 people

About

Finding a great startup job should not feel like a second job. Weekday AI brings the most exciting roles from premium YC and VC-backed startups into one place. Our team hand-picks every listing, so you skip the agency spam and the dead links and go straight to companies building things that matter. Why people use Weekday AI? Curated roles from premium YC and VC-backed startups Fresh jobs every week, picked by humans AI that helps you apply in minutes Free to join Your next role should come from a company you are proud to work at. We help you find it. Browse live roles at jobs.weekday.works

Open positions

MLOps Engineer, LLM Systems (Serving, GPU Kernels, Profiling)

Remote · Canada

Design and evaluate complex MLOps tasks related to GPU kernels, performance profiling, and inference serving. Guide research teams to improve AI model performance and develop robust evaluation frameworks for training infrastructure.

P&C Actuary & Portfolio Risk Manager

Remote · Canada

Design realistic insurance pricing, reserving, and portfolio management scenarios to train AI models. Evaluate and grade AI-generated responses for mathematical accuracy, methodology, and actuarial standards.

PDF Annotation & Transcription Experts - Korean

Remote · Canada

Annotate the structural components of Korean documents and provide faithful transcriptions of text regions. Ensure high accuracy in component identification, reading order, and character-level transcription for AI training datasets.

Multiline P&C Underwriter

Remote · Canada

Design realistic underwriting scenarios and evaluate AI-generated responses against established industry standards. Provide expert feedback to a research team to improve model behavior regarding insurability, pricing, and risk assessment.

PDF Annotation & Transcription Experts - Japanese

Remote · Canada

Annotate the structure of Japanese documents by identifying and bounding regions such as titles, tables, and diagrams while establishing reading order. Perform faithful transcriptions of all text, including handwritten content, and link components to their respective figures or tables.

Reinsurance & Program Business Specialist

Remote · Canada

Design realistic risk-transfer and delegated-authority scenarios to train AI models on insurance reasoning. Evaluate AI-generated responses against market standards and provide feedback to improve model accuracy in treaty and program business contexts.

Complex Claims & Coverage Director

Remote · Canada

Design complex insurance claim scenarios and evaluate AI model outputs against senior technical standards. Provide expert feedback to improve AI reasoning regarding coverage, litigation strategy, and major-loss resolution.

Life & Annuity Specialist

Remote · Canada

Design realistic insurance scenarios and evaluate AI-generated responses against industry standards for accuracy and suitability. Provide written feedback to the research team to improve model behavior regarding mortality risk and long-horizon guarantees.

Disability Claims & Underwriting Specialist

Remote · Canada

Design realistic disability adjudication scenarios and evaluate AI model outputs against industry standards. Create high-quality reference responses and provide feedback to improve model reasoning regarding medical and vocational evidence.

STEM PhDs and Technical Domain Experts

Remote · Canada

Contribute subject matter expertise to create high-quality data for state-of-the-art large language models. Develop complex problems within your specific technical domain to advance AI innovation.

Policy Administration & Insurance Operations Manager

Remote · Canada

Design and evaluate realistic insurance policy-processing scenarios to train AI models on operational standards. Create high-quality reference responses and grade AI outputs for accuracy, completeness, and procedural adherence.

Public Sector / Legal / GTM Experts

Remote · Canada, United Kingdom, United States

Review, assess, and provide structured feedback on domain-specific documents to ensure quality and accuracy. Contribute to high-impact evaluation projects by leveraging expertise in government, public sector, or GTM roles.

Real Estate / Property Professionals

Remote · Canada, United Kingdom, United States

Review, assess, and provide structured feedback on domain-specific documents related to real estate and property management. Ensure the quality, accuracy, and relevance of the evaluated content.

Retail / Clienteling professionals

Remote · Canada, United Kingdom, United States

You will review, assess, and provide structured feedback on domain-specific documents to ensure quality and accuracy. This role involves contributing to high-impact evaluation projects within a retail and client-facing sales context.

Job Seeker - New Grad

Remote · Canada, United Kingdom, United States

Review, assess, and provide structured feedback on domain-specific documents to ensure quality and accuracy. Contribute to high-impact evaluation projects by leveraging domain expertise.

Finance / IR experts

Remote · Canada, United Kingdom, United States

Review, assess, and provide structured feedback on domain-specific documents to ensure quality and accuracy. Contribute to high-impact evaluation projects using your financial expertise.

GTM / Marketing Experts

Remote · Canada, United Kingdom, United States

You will review, assess, and provide structured feedback on domain-specific marketing documents to ensure quality and accuracy. This role involves contributing to high-impact evaluation projects while working independently.

Education / Student

Remote · Canada, United Kingdom, United States

You will review, assess, and provide structured feedback on domain-specific documents to ensure quality and accuracy. This role involves contributing to high-impact evaluation projects while working independently.

Finance / Business Ops Experts

Remote · Canada, United Kingdom, United States

Professionals will review, assess, and provide structured feedback on domain-specific documents to ensure quality and accuracy. The role involves contributing to high-impact evaluation projects while working independently.

Product / Platform Experts

Remote · Canada, United Kingdom, United States

Review, assess, and provide structured feedback on domain-specific documents to ensure quality and relevance. Contribute to high-impact evaluation projects by leveraging platform-focused product management expertise.