Weekday (YC W21)

Artificial Intelligence

• Red team conversational AI models and agents using jailbreaks, prompt injections, misuse cases, bias exploitation, and multi-turn manipulation
• Generate human data by annotating failures, classifying vulnerabilities, and flagging systemic risks
• Follow taxonomies, benchmarks, and playbooks to keep testing consistent
• Produce reproducible reports, datasets, and attack cases for customers
• Uncover vulnerabilities automated tests miss
• Deliver reproducible artifacts that strengthen customer AI systems
• Expand evaluation coverage by testing more scenarios and reducing production surprises

AI Safety Expert, English, Finnish

SEO Marketing

• Own and continuously improve the brand's Page One search presence across Google and other relevant search ecosystems
• Develop strategies to ensure top search results are dominated by authoritative, accurate, and trusted brand or third-party properties
• Claim, optimise, maintain, and regularly refresh profiles across LinkedIn, Medium, industry directories, review platforms, and other high-authority websites
• Monitor brand search results, online mentions, reviews, media coverage, and reputation signals across relevant digital channels
• Develop and publish high-quality, SEO-optimised content designed to strengthen positive brand narratives and improve search visibility
• Build a content defence strategy supporting reputation protection through authoritative websites, editorial content, digital PR, and organic search
• Develop relationships with journalists, industry publications, influencers, and high-authority websites to secure press mentions, guest posts, and earned media opportunities
• Develop rapid-response content and PR strategies when reputation risks or negative narratives emerge
• Coordinate multiple content assets and distribution channels to strengthen positive search visibility during reputation challenges
• Build and grow a genuine customer advocacy community
• Work with Customer Success and other teams to identify brand advocates and develop advocacy initiatives
• Encourage positive customer stories, reviews, testimonials, and community participation while maintaining authenticity and compliance with platform policies
• Develop and maintain reputation monitoring systems using Google Alerts, Mention, Brand24, or similar platforms
• Identify emerging reputation risks, negative narratives, search trends, and potential digital threats
• Track SEO, reputation, content, media, and search performance metrics and use insights to improve strategy
• Research developments in SEO, AI search, LLM-driven discovery, GEO, digital PR, and reputation management
• Adapt strategies as search algorithms, platform policies, AI search behaviour, and online trends evolve
• Collaborate with internal teams to align reputation, SEO, content, customer experience, and communications initiatives
• Develop scalable processes and systems that improve the organisation's ability to protect and strengthen its digital reputation

Brand Reputation Manager – SEO, PR

Financial Planning and Analysis

• Lead and support financial planning and analysis, including annual budgets, forecasts, long-term plans, and periodic financial updates
• Prepare monthly, quarterly, and annual management reports covering revenue, expenses, profitability, cash flows, and key financial metrics
• Analyze actual financial performance against budgets, forecasts, and previous periods, identifying variances and business drivers
• Develop and maintain financial models for forecasting, scenario analysis, business performance reviews, and strategic decision-making
• Partner with business teams to gather financial and operational inputs and ensure accurate, consistent planning assumptions
• Prepare dashboards and presentations for senior management highlighting financial trends, risks, opportunities, and areas requiring attention
• Support business planning by evaluating revenue opportunities, cost structures, resource requirements, and financial implications of strategic initiatives
• Conduct profitability, cost, margin, and variance analysis across business units, products, services, or functions
• Develop financial scenarios and sensitivity analyses to evaluate changing business assumptions
• Track key performance indicators and establish financial and operational metrics to monitor business performance
• Collaborate with accounting and finance teams during month-end and year-end processes to ensure accurate reporting and reconciliation
• Identify opportunities for process improvements, automation, and standardization within FP&A and management reporting
• Provide ad-hoc financial analysis and insights to support management decisions and business reviews

Web Designer

• Own the end-to-end design and development of websites, landing pages, and microsites
• Create wireframes, layouts, visual concepts, and high-fidelity web designs based on project requirements
• Build responsive websites using Webflow, Framer, Wix Studio, or similar platforms
• Translate approved designs into polished, functional, and deployment-ready websites
• Create engaging animations, interactions, transitions, and dynamic web elements where appropriate
• Ensure websites deliver a consistent and intuitive experience across desktop, tablet, and mobile devices
• Apply brand guidelines consistently across web pages and digital touchpoints
• Collaborate with stakeholders to understand requirements, gather feedback, and manage revisions efficiently
• Maintain high standards of visual design, typography, spacing, layout, usability, and overall digital polish
• Deliver projects within agreed timelines while maintaining quality and attention to detail
• Take ownership of the pilot microsite/landing page from concept through final deployment
• Ensure the final website is responsive, functional, visually consistent, and ready for production

No-Code Web Designer, Developer

Insurance

• Design realistic scenarios involving treaty and facultative reinsurance, attachment and exhaustion, cessions, recoverables, bordereaux, delegated authority, program governance, fronting, captives, and risk participation
• Create structure comparisons, submission analyses, contract summaries, program reviews, counterparty assessments, and risk-transfer recommendations
• Write “golden” reference responses at experienced reinsurance and program-business quality
• Grade AI-generated responses against structured rubrics for structural accuracy, contract logic, financial understanding, stakeholder roles, and market realism
• Identify misunderstandings of layers, limits, retentions, commissions, claims control, collateral, counterparty exposure, and carrier-MGA responsibilities
• Provide written feedback used by the research team to improve model behavior
• Participate in onboarding office hours and calibration sessions
• Work a minimum of 20 hours per week, ideally 40+

Reinsurance & Program Business Specialist

Full-stack Engineer

• Select tasks from a pre-validated pool of C repositories pinned to specific git commits
• Explore repositories and relevant pull request or issue history to understand subsystems
• Rewrite task questions to challenge advanced coding agents while remaining well-defined
• Adjust rubrics and foils to reward correct reasoning and reject plausible but incorrect answers
• Run the full Studio validation loop: Check, Golden, Run, Analyze
• Document work in task READMEs and submit tasks for expert review
• Address reviewer feedback on returned tasks
• Build codebase-exploration tasks for reinforcement-learning environments that train AI agents to reason about unfamiliar software repositories

Software Engineer, C - Codebase Q&A

General

• Design realistic scenarios involving needs analysis, product selection, illustrations, medical and financial underwriting, table ratings, replacements and 1035 exchanges, policy loans, surrenders, lapse and reinstatement
• Create coverage recommendations, illustration comparisons, underwriting assessments, suitability rationales, replacement analyses and policy-service determinations
• Write “golden” reference responses at experienced life and annuity practitioner quality
• Grade AI-generated responses against structured rubrics for product accuracy, suitability, mathematical correctness and disclosure adequacy
• Identify unsupported illustration assumptions, unsuitable recommendations, confusion between product types or tax treatments, and failures to apply replacement or disclosure requirements
• Provide written feedback used by the research team to improve model behavior
• Participate in onboarding office hours and calibration sessions

Life and Annuity Specialist

Director

• Design realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds, multiple carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlement strategy
• Create complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations
• Write “golden” reference responses at senior technical claims quality
• Grade AI-generated responses against structured rubrics for policy analysis, strategic judgment, factual support, stakeholder awareness, and escalation discipline
• Identify claim-handling positions that are internally inconsistent, unsupported by the record, operationally unrealistic, or outside the authority of a non-lawyer claims professional
• Provide written feedback to improve model behavior
• Participate in onboarding office hours and calibration sessions
• Train frontier AI models using high-quality insurance reasoning data

Complex Claims and Coverage Director

• Evaluate AI-generated financial plans, budgets, forecasts, and other financial management artifacts for quality and accuracy
• Compare AI-generated responses head-to-head based on financial soundness, regulatory compliance, and analytical rigor
• Review financial scenarios involving cash flow oversight, budgeting, pricing decisions, and financial reporting
• Provide expert feedback to help evaluate and improve AI systems

Financial Manager

Evaluator

• Evaluate AI-generated artifacts against domain-specific quality rubrics.
• Identify factual, aesthetic, and presentation errors.
• Provide clear, structured written feedback.

Biology / Environmental Science Evaluator

Content Writer

• Use your voice to compose messages, emails, and notes across everyday apps
• Direct the AI to generate images, format text, apply spreadsheet formulas, and summarize documents
• Record accurate transcripts of spoken queries and produce cleaned-up transcripts
• Rate the AI's responses
• Log task data in a structured tracking sheet
• Upload supporting recordings to a shared drive
• Capture and evaluate real, natural voice interactions with a next-generation AI assistant

Bilingual Writer – Mandarin Chinese, Traditional

• Use your voice to compose messages, emails, and notes across everyday apps
• Direct the AI to generate images, format text, apply spreadsheet formulas, and summarize documents
• Record accurate transcripts of spoken queries and produce cleaned-up transcripts
• Rate the AI's responses
• Log task data in a structured tracking sheet
• Upload supporting recordings to a shared drive
• Complete technical setup and onboarding for the project

Bilingual Writer – Korean

Actuary

• Design realistic scenarios involving loss costs, rate indications, trend, development, credibility, segmentation, reserving, profitability, capital, catastrophe exposure, and portfolio concentration
• Create pricing analyses, reserve reviews, portfolio diagnostics, assumption critiques, sensitivity analyses, and management recommendations
• Write “golden” reference responses at experienced actuarial and portfolio-risk quality
• Grade AI-generated responses against structured rubrics for mathematical accuracy, assumption quality, methodology, interpretation, and communication
• Identify calculation errors, unsupported assumptions, misuse of actuarial methods, confusion of correlation with causation, and recommendations not supported by data
• Provide written feedback used by the research team to improve model behavior
• Participate in onboarding office hours and calibration sessions

P&C Actuary – Portfolio Risk Manager

Japanese

• Open and check provided PDF-page tasks; confirm the page is in Japanese, legible, contains real content, and has no personal details
• Identify and bound every meaningful page region, assign component types, and set reading-order indices
• Link regions to their associated figures or tables using parent component identifiers
• Transcribe all text exactly as shown, including kanji, hiragana, katakana, furigana, and handwriting; flag illegible regions
• Capture language, document type, source, page dimensions, and table, formula, and handwriting flags
• Review colleagues' work end to end as a second Japanese expert

PDF Annotation, Transcription Expert – Japanese

Backend Engineer

• Select tasks from a pre-validated pool of Python repositories pinned to specific git commits
• Explore repositories and relevant PR or issue history to understand the target subsystem
• Rewrite questions to challenge frontier coding agents while remaining well-defined and answerable
• Adjust rubrics and foils to reward correct reasoning and reject plausible-but-wrong answers
• Run the full Studio validation loop: Check, Golden, Run, Analyze
• Document work in task READMEs and submit tasks for expert review
• Address reviewer feedback on returned tasks
• Build datasets that teach AI agents to reason about real Python codebases