Top Tech Jobs & Startup Jobs in Boston, MA

Lead the design, development, deployment, monitoring, and improvement of interconnected customer lifetime value models covering conversion, retention, premiums, and claim losses. Serve as a hands-on technical leader, guide modeling strategy, evaluate experiments and business impact, partner with engineering and business teams, support production ML systems, establish technical standards, and coach other data scientists.

Own the vision, strategy, and roadmap for Root’s pricing platform and machine learning infrastructure. Lead engineering and partner with data science, actuarial, and engineering teams to improve pricing workflows, model development, deployment, monitoring, and regulatory operations. Drive self-service tooling, LLM-enabled data science workflows, platform reliability, and nationwide expansion while translating business needs into product requirements and prioritized investments.

Lead the AI Platform team in building reliable, secure, observable infrastructure, shared services, deployment patterns, and operational practices for AI capabilities. Set technical priorities, coordinate cross-team dependencies, guide architecture and production operations, improve developer experience, and coach engineers while contributing to complex technical work.

Lead platform, infrastructure, and AI engineering teams to set multi-year technical strategy, improve reliability and security, drive AI platform and DevEx roadmaps, grow engineering managers, and align platform investments to measurable business outcomes.

Develop, test, deploy, and support resilient software solutions for Root’s payments and billing product domain. Collaborate with engineers and stakeholders to understand customer problems, communicate technical work, improve code and processes, and resolve production incidents affecting customers. The role requires software engineering experience, Ruby on Rails or equivalent expertise, and familiarity with React or React Native.

Leads engineering for one or more product-domain teams, partnering with Engineering Managers, Product, Data Science, Analytics, and Insurance stakeholders. Responsibilities include setting technical strategy and roadmaps, coaching engineers, driving cross-team initiatives, contributing code, leading incident response and resiliency improvements, and establishing engineering standards. Requires strong Ruby on Rails expertise, Rust familiarity, software leadership experience, and excellent communication skills.

Leads Root’s SEC and US GAAP financial reporting, technical accounting policy, disclosure controls, audit coordination, and accounting standards implementation. Oversees complex accounting analyses involving insurance, investments, debt, leases, and statutory reporting. Partners with cross-functional leaders, auditors, regulators, and investors while improving reporting systems and close processes. Manages and develops the financial reporting team and prepares Audit Committee and Board materials.

Lead development and productionization of telematics pricing and underwriting models. Responsibilities span statistical modeling, feature engineering, dataset and pipeline development, model deployment, monitoring, data quality validation, troubleshooting, regulatory support, and collaboration with pricing, actuarial, product, engineering, and compliance teams.

Leads corporate actuarial activities spanning capital modeling, enterprise risk management, reinsurance, reserving, stress testing, ORSA, and regulatory support. The role develops models, evaluates reinsurance impacts, analyzes reserve adequacy, supports financial strategy, automates actuarial processes, and collaborates with Data Science, Finance, Underwriting, Claims, and Accounting. It also presents technical findings and may mentor junior staff or manage direct reports.

Lead and grow AI Platform and AI Enablement engineering teams building infrastructure, tooling, and integrations for AI features. Define AI engineering roadmap with product and data science partners, set standards for reliability, observability, security, and responsible AI, manage and develop engineers, engage in code/design reviews, and coordinate cross-team delivery with Platform and Data teams.