Jerry

Content Marketing Manager

• Overhaul existing customer communications, including CRM, email, SMS, and in-app copy
• Work closely with Product, Design, Growth, and Customer Insights teams
• Shape brand voice and messaging for new products and campaigns
• Build a team to manage organic GTM launches and social media presence

Head of Content Design

Growth Marketing

• Own end-to-end channel expansion: research, prioritize, launch, and iterate across a diverse mix of paid and partnership-based channels
• Shape the innovative channel roadmap
• Apply strong marketing fundamentals across varied and novel channel contexts
• Pioneer the adoption of AI agents in marketing operations
• Design and execute rigorous experiments
• Analyze performance across full-funnel metrics

Associate Director, Growth Marketing – Innovative Channels

Backend Engineer

• evolve our current automation systems to a robust, fault-tolerant framework
• lead incremental refactoring of our existing automation systems
• use an AI-first approach to building the next generation of internal tools

Tech Lead, Core Backend

Attorney

• own corporate compliance & governance
• lead legal research & applied analysis
• drive resolution of complex issues
• partner cross-functionally on product & compliance
• strengthen IP and protect the brand
• run tight audits
• build systems, not just outputs

Legal Researcher

Engineering Manager

• Evolve automation systems into a robust, fault-tolerant framework
• Lead incremental refactoring of automation systems
• Design and implement new standards and ensure system predictability and testability
• Use AI-first approach to build next generation internal tools

Engineering Manager, Distributed Systems

Art Director

• Overhauling existing customer communications, including our CRM, email, SMS, and in-app copy
• Work closely with our Product, Design, Growth, and Customer Insights team to understand how to build trust and engagement
• Taking bigger creative swings to help us stand out online
• Own the positioning and messaging for new products and build a team to manage organic GTM launches and our social media presence

Creative Director, Copy

Product Manager

• lead end-to-end product development for Jerry's AI-powered customer experiences and internal AI platform
• partner with engineers and prompt engineers to design and iterate on AI architectures
• be the bridge between engineering and the rest of the org
• own metrics that matter and drive systematic improvement through data and experimentation
• work directly with our partners at OpenAI to evaluate new models and capabilities

Senior Product Manager, AI Agents – Platform

• lead end-to-end product development for AI-powered customer experiences and internal AI platform
• collaborate with engineers to design and iterate on AI architectures and user experience
• bridge between engineering and other teams advocating AI best practices
• own metrics that matter to drive systematic improvement
• work with partners at OpenAI to evaluate new models and capabilities

Senior Product Manager, AI Agents and Platform

• Own the end-to-end process of launching new insurance carrier partners and products
• Improve quoting system logic and eligibility rules
• Diagnose customer drop-out points in the quoting journey
• Maintain the integrity of underwriting inputs
• Keep median quote latency between 5-15 seconds

Product Manager, Insurance – Core Product

• Own Entity Compliance: Keep corporate entities in "Good Standing" across the US and Canada.
• Protect the Brand: Draft and initiate cease-and-desist workflows for infringements.
• Investigate & Educate: Act as the first line of defense for complex consumer escalations.
• Drive Product & Process Improvements: Review product and process for compliance.
• Run Tight Audits: Lead compliance audits across operations.
• Automate Everything: Use AI and low-code tools to create scalable workflows.

Operations Analyst – Legal & Compliance

• Own Entity Compliance by keeping corporate entities in "Good Standing" across the US and Canada.
• Monitor our intellectual property presence and draft cease-and-desist workflows.
• Act as the first line of defense for complex consumer escalations.
• Review product and process for compliance, partner with Engineering and Product teams.
• Lead compliance audits across operations to ensure regulatory standards are met.

Operations Associate – Legal & Compliance

• Own Entity Compliance across the US and Canada.
• Monitor our intellectual property presence and hunt down infringements.
• Act as the first line of defense for complex consumer escalations.
• Review product and process for compliance.
• Lead our compliance audits across operations.
• Use AI and low-code tools to automate legal workflows.

Legal Operations Associate

• evolve current automation systems to a robust, fault-tolerant framework
• managing external interface changes gracefully and scaling across dozens of new categories with minimal manual intervention
• deep in the code, learning both technical and business sides of core product
• lead incremental refactoring of existing automation systems
• designing and implementing new standards and pairing with engineers
• using an AI-first approach to build the next generation of internal tools

Engineering Manager, Core Product Engine

Data Scientist

• Participate in the full modeling lifecycle, from statistical analysis and experimentation to building, validating, and iterating on machine learning models that address critical business challenges
• Own the data foundation by preparing, cleaning and transforming raw, complex data into high-quality features for modeling
• Investigate data discrepancies and design automated frameworks to ensure data accuracy
• Collaborate with data Engineering and product teams to drive the data strategy
• Create and maintain clear documentation for data sources, cleaning processes, and variable definitions

Junior Applied Data Scientist

• Participate in the full modeling lifecycle, from statistical analysis and experimentation to building, validating, and iterating on machine learning models that address critical business challenges
• Own the data foundation by preparing, cleaning and transforming raw, complex data into high-quality features for modeling
• Investigate data discrepancies and design automated frameworks to ensure data accuracy
• Act as a strategic liaison, collaborating with data engineering and product teams to drive the data strategy and definition of our centralized feature store
• Create and maintain clear documentation for data sources, cleaning processes, and variable definitions