Weekday (YC W21)

Project Manager

• Map and continuously refine the end-to-end customer journey, identifying key touchpoints, drop-offs, and growth opportunities
• Segment users based on behavior, demographics, lifecycle stage, and intent to enable targeted marketing strategies
• Plan and execute lifecycle campaigns across email, SMS, push notifications, in-app messaging, and web channels
• Build and optimize automated marketing workflows to deliver timely, personalized communication at scale
• Leverage data to drive personalization strategies, improving engagement, retention, and conversion rates
• Track and analyze key performance metrics across activation, engagement, and lifecycle stages
• Conduct A/B testing to optimize messaging, timing, and campaign effectiveness
• Ensure seamless cross-channel user experience through consistent messaging and integration
• Collaborate with product, sales, and support teams to align lifecycle strategies with business goals
• Maintain clear documentation of campaigns, workflows, and performance insights for continuous improvement

Lifecycle Product Marketing, Project Manager

General Counsel

• Perform simulated contract negotiations and redlining exercises, assessing AI-generated suggestions for accuracy, risk identification, and legal soundness
• Review AI-generated responses to contract scenarios and provide structured, actionable feedback to improve performance
• Evaluate outputs related to SaaS agreements, identifying gaps, risks, and inconsistencies
• Collaborate with product and research teams to refine training data, annotation frameworks, and best practices for AI-driven contract review systems
• Contribute to the development of high-quality datasets that improve legal AI precision and reliability

Attorney

• Conduct simulated contract negotiations and redlining exercises, evaluating AI-generated suggestions for legal accuracy and risk identification
• Review AI responses to commercial contract scenarios and provide structured, actionable feedback
• Assess SaaS agreements for clarity, compliance, and potential legal risks
• Collaborate with product and research teams to refine training datasets, annotation standards, and best practices for AI-driven contract review
• Help improve the quality and reliability of AI systems used in legal contracting workflows

Contracting Attorney

Artificial Intelligence

• Design, develop, and implement AI-driven solutions to streamline end-to-end policy administration processes, including policy issuance, mid-term endorsements, and renewals.
• Analyze and interpret complex insurance policy coverage, translating business rules into scalable AI/ML models and decision frameworks.
• Collaborate with underwriting, operations, and compliance teams to automate policy workflows while maintaining high accuracy and auditability.
• Build intelligent systems for document processing, policy validation, and exception handling using NLP, rule engines, and predictive models.
• Enhance renewal strategies through data-driven insights, customer behavior analysis, and risk profiling.
• Ensure AI systems align with regulatory requirements across jurisdictions, incorporating compliance checks into automated workflows.
• Monitor model performance, accuracy, and bias, continuously improving systems based on feedback and evolving regulatory standards.
• Support integration of AI solutions with policy administration systems (PAS), core insurance platforms, and third-party data providers.
• Provide domain expertise in interpreting policy wording, exclusions, and coverage limits to ensure correct system outputs.

Insurance Policy Administration AI Expert

Actuary

• Evaluate and optimize portfolio performance through detailed loss ratio and combined ratio analysis
• Conduct comprehensive portfolio risk assessments using statistical models and AI-driven techniques
• Focus on catastrophe modeling and exposure management, enhancing traditional modeling using machine learning techniques
• Leverage AI/ML techniques to automate actuarial workflows and improve predictive modeling

Risk & Actuarial AI Expert

Financial Planning and Analysis

• Actively manage and optimize the month-end and year-end close processes, leveraging AI-driven tools and automation techniques to reduce cycle time and improve accuracy
• Coordinate cross-functional inputs, identify bottlenecks, and implement intelligent solutions to streamline reconciliations, variance analysis, and reporting timelines
• Prepare, review, and validate journal entries, accruals, and adjustments to ensure completeness and accuracy by applying accounting principles alongside automated checks and anomaly detection models
• Design and refine workflows that enable consistent and audit-ready financial data
• Prepare and review financial statements, including balance sheets, income statements, and cash flow statements, enhancing reporting quality through automated variance analysis, trend identification, and predictive insights
• Collaborate with stakeholders to ensure that reports are clear, compliant, and aligned with business objectives
• Contribute to the integration of AI into financial reporting processes by evaluating tools, building use cases, and supporting implementation
• Work with data teams to structure financial data for machine learning applications and continuously improve reporting frameworks through automation and intelligent analytics

Financial Reporting AI Expert

• Design, implement, and optimize intelligent systems across claims intake, investigation, and adjudication workflows
• Develop AI models for automated data extraction, classification, and triaging of claims
• Leverage machine learning to identify anomalies, detect potential fraud, and support decision-making
• Help design AI-assisted decision engines for claim outcomes based on policy coverage and risk profiles
• Develop predictive models for accurate reserve setting and loss estimation
• Implement AI tools to track recovery potential and improve recovery rates

Insurance Claims Management AI Expert

• Lead the budgeting, forecasting, and variance analysis processes across business units, ensuring accuracy, transparency, and alignment with organizational goals.
• Develop dynamic financial models that incorporate AI/ML techniques to improve forecast precision and identify trends, risks, and opportunities.
• Perform detailed variance analysis (actual vs. budget/forecast), providing clear explanations and actionable recommendations to senior leadership.
• Design and implement long-range planning frameworks, including multi-year financial projections and strategic roadmaps.
• Build scenario models to evaluate the financial impact of business decisions, market changes, and operational strategies.
• Define, monitor, and refine key performance indicators (KPIs) that align with business objectives and drive performance accountability.
• Develop AI-powered dashboards and reporting tools for real-time KPI tracking and decision support.
• Collaborate cross-functionally with finance, operations, product, and data teams to integrate financial insights into business strategies.
• Automate repetitive FP&A processes using AI tools, improving efficiency and reducing manual effort.
• Translate complex financial data into clear, concise insights for stakeholders, including senior management and executives.

Financial Planning & Analysis AI Expert

• Managing and optimizing end-to-end account reconciliation processes
• Performing detailed account reconciliations, identifying discrepancies, conducting variance analysis
• Automating reconciliation workflows using AI tools
• Handling intercompany transactions and eliminations
• Ensuring accurate recording and reconciliation of intercompany balances
• Contributing to the design and maintenance of the chart of accounts
• Evaluating, implementing, and optimizing AI-powered reconciliation tools

Ledger and Reconciliation AI Expert

• Designing, implementing, and optimizing AI-powered solutions for financial compliance and control processes
• Leveraging automation and analytics tools to ensure adherence to GAAP and IFRS requirements
• Collaborating with finance, audit, and technology teams to strengthen internal control frameworks
• Evaluating existing controls and implementing intelligent monitoring systems for ongoing compliance
• Supporting internal and external audits using AI tools to streamline audit preparation, documentation, and evidence gathering
• Ensuring accurate application of revenue recognition standards (e.g., ASC 606 / IFRS 15) and supporting lease accounting processes (ASC 842 / IFRS 16) with automation tools

Compliance and Controls AI Expert

• Lead and support tax provision and planning activities by integrating AI-driven tools to improve accuracy, forecasting, and efficiency in tax calculations and reporting.
• Design and implement intelligent solutions to streamline sales tax, payroll tax, and multi-jurisdictional tax compliance, ensuring adherence to varying regional and international tax laws.
• Analyze complex tax datasets using advanced analytics and machine learning models to identify risks, opportunities, and cost-saving strategies.
• Oversee and enhance regulatory filing and reporting requirements, ensuring timely and accurate submissions in line with statutory obligations.
• Collaborate with cross-functional teams including finance, legal, and technology to embed AI solutions into existing tax workflows.
• Monitor evolving tax regulations and assess their impact on automated systems and organizational compliance strategies.
• Develop and maintain documentation for AI-driven tax models, ensuring transparency, auditability, and alignment with governance standards.
• Support audits by providing AI-backed insights, reconciliations, and documentation to internal and external stakeholders.
• Continuously evaluate and improve AI models for tax applications, ensuring scalability, reliability, and compliance with regulatory frameworks.

Tax AI Expert

• Evaluate Investment Opportunities & ROI: Analyze a wide range of investment opportunities, including product development, technology adoption, acquisitions, and operational improvements. Build and maintain financial models to assess ROI, IRR, NPV, and payback periods. Leverage AI and predictive analytics to enhance forecasting accuracy and scenario planning. Translate complex analyses into clear, actionable recommendations for stakeholders.
• Build vs. Buy Decision Frameworks: Develop structured frameworks to assess whether capabilities should be built internally or acquired externally. Incorporate cost, time-to-market, scalability, strategic control, and risk factors into decision-making models. Use data-driven insights to quantify trade-offs and support leadership in making informed choices aligned with long-term business goals.
• Prioritize Initiatives Under Constraints: Design prioritization models that balance strategic impact, financial return, and resource availability. Apply optimization techniques and AI tools to rank initiatives across competing demands. Work closely with cross-functional teams to ensure alignment between strategic priorities and execution capacity.
• AI-Driven Decision Support: Implement and utilize machine learning models and decision-support systems to enhance capital allocation processes. Continuously improve data pipelines, model accuracy, and reporting capabilities. Identify opportunities to automate repetitive analysis and improve decision speed without compromising quality.
• Stakeholder Collaboration: Partner with finance, product, engineering, and leadership teams to gather inputs, validate assumptions, and align on priorities. Communicate insights effectively to both technical and non-technical audiences, ensuring transparency in decision-making.
• Performance Monitoring & Optimization: Track the performance of funded initiatives against projected outcomes. Conduct post-investment reviews to refine models and improve future allocation decisions. Establish feedback loops to ensure continuous improvement.

Capital Allocation AI Expert

• Develop, maintain, and enhance robust operating models that capture business drivers, revenue streams, cost structures, and capital allocation strategies.
• Build detailed cash flow forecasts, including short-term liquidity planning and long-term financial projections, ensuring alignment with business goals.
• Apply AI and data-driven techniques to automate, optimize, and improve the accuracy of financial models and forecasting processes.
• Conduct sensitivity analysis and scenario planning, including downside and stress-case modeling, to evaluate financial resilience under varying market conditions.
• Translate business and corporate strategy into clear financial implications, enabling leadership to assess profitability, risk exposure, and investment priorities.
• Collaborate cross-functionally with product, operations, and leadership teams to gather inputs and validate model assumptions.
• Create dashboards, reports, and visualizations that communicate complex financial insights in a clear and actionable manner.
• Support strategic initiatives such as fundraising, M&A analysis, pricing strategies, and cost optimization efforts.

Financial Modeling AI Expert

• Lead the creation of robust, data-backed business cases for new initiatives, investments, and strategic projects.
• Own the development and continuous refinement of unit economics frameworks across products, geographies, or customer segments.
• Partner closely with senior leadership and board members to deliver clear, concise, and insight-rich financial narratives.
• Integrate machine learning models and automation tools into financial planning and analysis (FP&A) processes.
• Design and track key performance indicators (KPIs) aligned with business strategy.

Strategic Finance AI Expert

Business Development Rep

• Plan and design delivery routes utilizing Google Maps
• Oversee daily logistics and manage deliveries
• Contact customers to explain services through cold calling
• Maintain and monitor toy inventory
• Address customer inquiries and offer support