Weekday (YC W21)

Accountant

• Design realistic scenarios from tax work, including return preparation (1040 / 1120 / 1120-S / 1065), tax provision (ASC 740), responses to notices / IDRs and controversy support, tax planning, and estimated payments
• Review and compare AI-generated tax outputs for technical accuracy and defensible positions
• Provide clear written feedback that improves how AI performs tax tasks
• Collaborate asynchronously with the research team

Tax Accountant – Specialist

Software Engineer

• Design, develop, configure, and maintain Guidewire applications and solutions
• Work extensively with Guidewire PolicyCenter and cloud-based Guidewire platforms
• Develop and customize application functionality based on business and technical requirements
• Configure and enhance PCF, Rules Engine, Data Model, and other Guidewire components
• Develop and maintain integrations between Guidewire applications and external systems
• Build and consume REST APIs to support application and system integrations
• Analyze business requirements and translate them into effective technical solutions
• Support insurance product configuration and workflows for Property & Casualty insurance lines
• Work with Professional Liability and Commercial Auto insurance processes and related application requirements
• Participate in system design, development, testing, debugging, deployment, and production support activities
• Troubleshoot complex application and integration issues and implement effective solutions
• Collaborate with cross-functional teams in an Agile development environment
• Ensure application solutions are scalable, maintainable, secure, and aligned with development best practices
• Contribute to technical documentation, code reviews, and continuous improvement initiatives

Guidewire Developer

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

Bilingual Writer – Portuguese, Brazil

• 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
• Use a specialized app on a Mac to complete everyday voice-based tasks and evaluate AI interactions

Bilingual Writer – Italian

Compliance

• Construct scenarios spanning regulatory compliance program design, agency investigations and enforcement actions, and rulemaking or comment processes
• Build tasks across financial services regulation, healthcare and FDA regulation, antitrust and competition law, data privacy and cybersecurity regulation, and environmental and energy regulation
• Develop scenarios involving regulatory tracking platforms, compliance management systems, and agency filing systems used across regulated industries
• Apply regulatory law methodologies, including regulatory interpretation, compliance risk assessment, and enforcement response strategy
• Produce reference compliance memoranda, regulatory filings, and enforcement response documents for US and international regulatory tracks
• Author rubrics that distinguish authentic regulatory judgment from generic law school or bar exam-level recall

Regulatory Law Expert

Recruitment

• Manage the end-to-end recruitment process, including manpower requirements, sourcing, screening, interviewing, selection, offer management, and onboarding coordination
• Partner with hiring managers and business stakeholders to define candidate profiles and hiring strategies
• Lead recruitment across multiple positions, functions, experience levels, and business units
• Develop sourcing strategies using job portals, professional networks, employee referrals, social media, databases, and other talent channels
• Improve recruitment processes to enhance time-to-hire, quality of hire, cost efficiency, and candidate experience
• Manage and prioritize multiple recruitment mandates while meeting hiring timelines
• Lead, mentor, and manage a team of recruiters
• Allocate recruitment requirements and monitor progress against hiring goals
• Track recruitment metrics including open positions, profiles sourced, interviews scheduled, selection ratios, offer-to-joining ratios, and time-to-fill
• Conduct recruitment team reviews and identify sourcing and conversion improvements
• Build relationships with internal stakeholders, hiring managers, business leaders, and HR teams
• Provide regular updates on hiring progress and resolve recruitment-related challenges
• Ensure timely candidate communication and a professional candidate experience
• Maintain recruitment records, candidate databases, trackers, and reports
• Stay updated on talent-market trends, competitor hiring practices, sourcing techniques, and recruitment technology

Recruitment Assistant Manager

Customer Success Manager

• Evaluate AI-generated artifacts against domain-specific quality rubrics
• Identify factual, aesthetic, and presentation errors
• Provide clear, structured written feedback
• Review and assess AI-generated documents, spreadsheets, and slide decks for accuracy, rigor, and domain quality
• Apply deep subject-matter expertise to grade outputs

Data Quality, CRM Operations Evaluator

Operations

• Reconcile ledgers against custodian / bank statements
• Isolate and explain every residual difference
• Produce the signed-off reconciliation with adjusting entries
• Attribute NAV movements
• Flag components outside tolerance
• Write variance commentary
• Investigate trade breaks between two systems
• Identify root causes and classify breaks
• Propose fixes and draft investigation narratives
• Process corporate-action events and compute entitlements per account
• Handle payment / transfer exceptions by repairing, returning, or escalating them
• Match messy merchant / vendor descriptors to a canonical registry
• Complete self-contained operations exercises from mock files and produce analyst deliverables graded against a rubric

Investment Operations Analyst, Fund Accounting

Financial Planning and Analysis

• Design realistic scenarios from your work — operating budgets and rolling forecasts, flux / variance analysis and commentary, 13-week cash flow forecasts, daily cash positioning & bank administration, FX revaluation, debt / covenant compliance schedules, and formula-driven financial models
• Review and compare AI-generated FP&A / treasury outputs for accuracy and sound judgment on assumptions
• Provide clear written feedback that improves how AI performs planning and cash-management tasks
• Collaborate asynchronously with the research team

FP&A Analyst, Treasury

• Use your voice to compose messages, emails, and notes across everyday apps
• Direct the AI to take actions such as generating images, formatting text, applying spreadsheet formulas, or summarizing 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 and upload supporting recordings to a shared drive
• Complete a four-week project starting immediately

Bilingual Writer – Hindi

• Design realistic scenarios involving application intake, binding, issuance, endorsements, certificates, billing, audits, renewals, cancellations, reinstatements, and policy-document delivery
• Create processing instructions, transaction reviews, exception-handling plans, service communications, and operational quality checks
• Write “golden” reference responses at experienced insurance-operations quality
• Grade AI-generated responses against structured rubrics for procedural accuracy, completeness, sequencing, and adherence to service standards
• Identify incorrect effective dates, missing documentation, improper transaction handling, and confusion between operational processing and substantive underwriting decisions
• Provide written feedback to improve model behavior
• Participate in onboarding office hours and calibration sessions

Policy Administration – Insurance Operations Manager

• Complete self-contained review and supervision exercises from mock files
• Produce draft-only compliance deliverables for each exercise
• QA completed periodic client reviews against a supervision control checklist
• Flag deficiencies with specific control citations and write audit-trail entries
• Review Reg BI / DOL rollover and trade / new-account attestations against reference procedures
• Flag non-compliant recommendations with citations
• Review outgoing client communications and marketing pieces against the SEC Marketing Rule and suitability guidelines
• Draft reviewer dispositions
• Supervise structured-product and alternative-investment books
• Flag restriction-code hits, recent-purchase patterns, and concentration thresholds
• Complete assessments involving periodic reviews, rollover recommendations, and marketing pieces

Securities & Wealth-Management Compliance, Supervisory Analyst

Sales

• Lead, motivate, and coach sales representatives to achieve and exceed individual and team targets
• Set performance goals and establish actionable plans
• Monitor team productivity, conversion rates, revenue, and customer engagement
• Conduct one-on-one coaching sessions, team reviews, and performance discussions
• Develop sales professionals through structured coaching, feedback, and continuous training
• Maintain strong personal sales performance and demonstrate effective sales techniques
• Develop and refine sales strategies, scripts, messaging, objection handling, and follow-up processes
• Improve lead engagement, prospecting, conversion, and customer retention
• Analyze sales data, identify performance gaps and root causes, and optimize processes
• Track key sales metrics and prepare performance updates and recommendations for management
• Investigate underperformance and develop action plans
• Improve forecasting, resource allocation, and sales execution using data-driven insights
• Support the team with complex prospects and challenging sales situations
• Improve prospect response rates, value communication, objection handling, and closing
• Maintain professionalism and customer experience across sales interactions
• Collaborate with colleagues and stakeholders from different countries and cultural backgrounds
• Organize focused team meetings and maintain communication in a fully remote environment
• Demonstrate accountability, reliability, and ownership of team outcomes

Sales Team Leader

Underwriter

• Design realistic scenarios involving short- and long-term disability claims, elimination periods, own-occupation and any-occupation definitions, residual and partial disability, offsets, recurrent disability, and claim duration management
• Create claim determinations, benefit calculations, medical and vocational evidence summaries, transferable-skills analyses, return-to-work plans, and appeal decisions
• Write “golden” reference responses at experienced disability-professional quality
• Grade AI-generated responses against structured rubrics for definitional accuracy, evidentiary support, benefit-calculation correctness, and procedural fairness
• Identify misapplied disability definitions, unsupported functional conclusions, missed offsets, incorrect benefit math, and failures to document the administrative record
• Provide written feedback used by the research team to improve model behavior
• Participate in onboarding office hours and calibration sessions