Jobs at Weekday, Inc.

Contribute transactional and corporate law expertise to train and evaluate AI models: design realistic deal scenarios, draft attorney-quality gold-standard responses, grade AI outputs with rubrics, provide written feedback to improve model reasoning, and participate in onboarding and calibration sessions.

Design, implement, and monitor AI/ML models to improve underwriting risk assessment, pricing, and portfolio management. Translate underwriting rules into data models, integrate models into workflows, analyze datasets for risk patterns, build decision-support tools, ensure compliance and fairness, and collaborate with underwriting, actuarial, product, and engineering teams.

Design, implement, and optimize AI-powered solutions to support financial compliance and controls. Monitor GAAP/IFRS adherence, automate controls and reporting, support internal/external audits, and manage complex accounting areas like revenue recognition and lease accounting while collaborating with finance, audit, and technology teams.

Lead modernization of month-end and year-end close processes using AI and automation. Prepare, review, and validate journal entries, accruals, and financial statements. Implement anomaly detection, automated reconciliations, variance analysis, and predictive insights. Collaborate with data teams to structure finance data for ML use cases and design audit-ready, scalable reporting workflows.

Design realistic, specialty-specific clinical case scenarios and gold-standard attending-level responses, evaluate and grade AI-generated outputs using structured rubrics, provide detailed written feedback to improve model clinical reasoning, and participate in onboarding, calibration, and review sessions in a fully remote, asynchronous contractor role (~20 hours/week).

Evaluate and assess financial statements, reports, models, and business documents for accuracy and completeness. Provide structured feedback per guidelines, identify inconsistencies, and recommend improvements while following detailed evaluation frameworks.

Analyze and classify technical content for security vulnerabilities, apply pattern recognition to improve AI model threat detection, design and evaluate security problems, and collaborate asynchronously with domain experts to produce high-quality outputs.

Manage and optimize end-to-end account reconciliations, intercompany eliminations, and chart-of-accounts governance. Identify discrepancies, perform variance analysis, and implement AI-driven automation and anomaly detection to reduce manual effort and accelerate close. Collaborate with cross-functional teams to resolve mismatches and improve financial data quality and reporting accuracy.

Build and maintain operating and cash-flow models, apply AI/ML and data techniques to automate forecasts, run sensitivity and scenario analysis, translate strategy into financial outcomes, support fundraising/M&A/pricing, and create dashboards and reports for stakeholders.

Act as the internal voice of the customer, partnering with Sales, Product, and Engineering to design and configure billing, revenue recognition, and invoicing solutions. Lead discovery with finance leaders, build demo/sandbox environments, respond to RFPs, document handoffs, and create onboarding materials while advocating customer needs to Product and Engineering.

Serve as the internal customer advocate and technical pre-sales lead for finance-heavy billing and revenue recognition solutions. Translate complex billing and revenue requirements into configured demos, sandbox environments, and solution documents. Partner with Sales, Product, and Engineering to support discovery, RFPs, implementations, and handoffs for enterprise customers.

Lead budgeting, forecasting, and variance analysis while building AI-driven financial models, scenario planning, KPIs, and dashboards. Automate FP&A processes, deliver insights to senior leaders, and collaborate with cross-functional teams to improve forecast accuracy and strategic decision-making.

Design, implement, and optimize AI-driven solutions across the claims lifecycle (intake, investigation, adjudication). Build ML models for data extraction, fraud detection, reserve setting, subrogation, and adjudication decision engines. Collaborate with underwriting, fraud, legal, and IT to integrate models into operations and improve efficiency, accuracy, and compliance.

Review and assess equity research, models, and market analyses to improve AI training data. Provide valuation, earnings forecasting, and investment memo feedback using long/short equity frameworks. Contribute to analytical materials, market sizing, and research summaries to enhance financial reasoning in foundational models.

Drive data-informed capital allocation by building financial models (NPV, IRR), applying AI/ML for forecasting and scenario planning, creating build-vs-buy and prioritization frameworks, implementing decision-support systems, collaborating with cross-functional stakeholders, and monitoring post-investment performance to refine allocation models.

Review and edit tasks created by professionals across industries to improve clarity, structure, and alignment with quality standards. Provide actionable feedback, apply consulting frameworks, and ensure consistency with project guidelines. Work asynchronously as an independent contractor for a remote AI research project.

Serve as the internal customer advocate and pre-sales technical lead for finance-focused enterprise deals. Configure complex billing, pricing, metering, invoicing, and revenue recognition workflows; build demo environments; engage finance leaders; support RFPs and sandbox configurations; document solutions and handoffs; feed product and engineering with customer insights.

Contract role combining actuarial science, risk management, and AI to improve portfolio performance. Responsibilities include loss and combined ratio analysis, portfolio risk assessment, catastrophe and exposure modeling, stress testing, and integrating ML to enhance pricing, reserving, and risk selection while collaborating with underwriting, finance, and product teams.

Design and implement AI/NLP solutions to automate insurance policy administration (issuance, endorsements, renewals). Translate policy language into models and rule engines, integrate with PAS, ensure regulatory compliance, monitor model performance, and support underwriting, operations, and exception handling.

Lead AI-enabled financial planning and strategic analysis, build data-backed business cases, refine unit economics, deliver executive-level insights, integrate ML into FP&A, and track KPIs to drive profitability and strategic decisions.