Jerry

AI Engineer

• Set the technical bar and shape architecture for chatbot systems as they scale
• Guide prompt engineering team development while maintaining sound architecture
• Build automations for record disputes, email/callout reduction, and document validation
• Evaluate emerging AI technologies including voicebots and computer-use agents
• Decide which AI technologies to invest in and build and ship them to production
• Partner with OpenAI to evaluate and deploy next-generation voice models and workflow automation
• Lead development of the next-generation AI system
• Expand voicebots into stateful, phone-based interactions
• Enable bots to navigate external systems directly to resolve complex issues efficiently and accurately

Software Architect, AI & Automation

Full-stack Engineer

• Set the technical bar for chatbot systems and shape the prompt engineering team's future work
• Maintain sound chatbot architecture as it scales
• Build automations for record disputes, email/callout reduction, and document validation
• Evaluate emerging AI technologies such as voicebots and computer-use agents
• Decide which technologies to invest in next
• Build and ship AI systems to production
• Partner with OpenAI to evaluate and deploy next-generation voice models and workflow automation
• Build the next-generation AI system for insurance quoting, document validation, stateful phone interactions, and direct navigation of external insurance systems

AI Product Engineer

Customer Support

• Take great care of customers by identifying coverage gaps, eligible discounts, and renewal increases
• Answer inbound calls from customers shopping for auto, home, motorcycle, and other insurance policies
• Assist policyholders with policy changes
• Learn the insurance product panel and Jerry app to guide customers toward suitable coverage
• Solve problems and remove barriers between customers and appropriate coverage
• Process service requests involving vehicles, drivers, lienholders, and policy documents
• Provide customer feedback to improve the product

Customer Experience Advocate

• Review Jerry’s Florida property tax appeal product and pressure-test its workflows
• Flag processes and product decisions that will not survive contact with Florida’s Value Adjustment Board system
• Clarify how Chapter 194, F.S. and DOR uniform rules 12D-9 and 12D-10 operate in practice
• Explain county-level differences among Florida Property Appraiser offices and VABs
• Guide TRIM notice timing, the 25-day filing window, DR-486 variants, e-filing versus paper, and the §194.014 partial-payment requirement
• Help build hearing and evidence flows involving comparable selection, evidence exchange windows, and condition-based arguments
• Advise the early-stage product team before customer-facing production launch

Subject Matter Expert, Florida Property Tax – Contract

• Clarify how Chapter 194, F.S. and DOR uniform rules 12D-9 and 12D-10 operate in practice
• Explain differences among Property Appraiser offices and VABs across Miami-Dade, Broward, Palm Beach, Hillsborough, Orange, Duval, Pinellas, and Lee counties
• Guide product development on TRIM notice timing, the 25-day filing window, DR-486 and variants, e-filing versus paper, and the §194.014 partial-payment requirement
• Help build an effective hearing and evidence flow covering comparable selection, 15-day and 7-day evidence exchange windows, and condition-based arguments
• Review the product being built and flag issues that will not survive contact with the Florida VAB process
• Advise the team and identify errors before they affect customers

Property Tax Specialist

• Review Jerry’s property tax appeal product and pressure-test its design before production
• Flag processes and product behavior that will not survive contact with Florida’s Value Adjustment Board system
• Clarify how Chapter 194, F.S. and DOR uniform rules 12D-9 and 12D-10 operate in practice
• Explain county-level differences across Miami-Dade, Broward, Palm Beach, Hillsborough, Orange, Duval, Pinellas, and Lee
• Guide TRIM notice timing, the 25-day filing window, DR-486 and variants, e-filing versus paper, and the §194.014 partial-payment requirement
• Help build hearing and evidence workflows involving comparable selection, evidence-exchange windows, and condition-based arguments
• Advise the early-stage product team on customer flows, backend authorization flows, and filing logic

Property Tax Advisor – Florida

• Review Jerry's property tax appeals product and pressure-test its workflows
• Flag processes or designs that will not survive contact with Florida's Value Adjustment Board system
• Clarify how Chapter 194, F.S. and DOR uniform rules 12D-9 and 12D-10 operate in practice
• Explain county-level differences among Miami-Dade, Broward, Palm Beach, Hillsborough, Orange, Duval, Pinellas, and Lee
• Guide TRIM notice timing, the 25-day filing window, DR-486 variants, e-filing versus paper, and the §194.014 partial-payment requirement
• Help build hearing and evidence workflows involving comparable selection, evidence exchange windows, and condition-based arguments
• Correct product logic and customer flows before production

Certified Appraiser, Property Tax Appeals – Florida

Advisor

• Review Jerry’s property tax appeal product and pressure-test its workflows
• Flag processes or designs that will not survive contact with Florida’s Value Adjustment Board system
• Clarify how Chapter 194, F.S. and DOR uniform rules 12D-9 and 12D-10 operate in practice
• Explain county-level differences among Florida Property Appraiser offices and VABs
• Guide TRIM notice timing, the 25-day filing window, DR-486 and variants, e-filing versus paper, and the §194.014 partial-payment requirement
• Help build hearing and evidence workflows involving comparable selection, evidence exchange windows, and condition-based arguments
• Correct product decisions before production and before they affect customers
• Advise the early-stage product team for approximately 5–10 hours per week by phone or video

Ad Valorem Assessment Advisor

Sales

• Go through (paid) training and insurance licensing (note: you must pass your licensing exam to legally sell insurance)
• Guide engaged users through the insurance purchasing process. There’s no cold-calling, these people have already started their insurance search in our app
• Simplify the Process: Help customers compare 55+ different insurance companies to find the one that fits their budget.
• Solve Problems: Listen to a customer’s concerns and find a solution that makes them feel confident in their choice.
• Close the Deal: Help customers finalize their new policy right then and there.

Sales Associate – Retail/Service Backgrounds Welcome

• Go through (paid) training and insurance licensing (note: you must pass your licensing exam to legally sell insurance).
• Guide engaged users through the insurance purchasing process.
• Simplify the Process: Help customers compare 55+ different insurance companies to find the one that fits their budget.
• Solve Problems: Listen to a customer’s concerns and find a solution that makes them feel confident in their choice.
• Close the Deal: Help customers finalize their new policy right then and there.

Insurtech Sales Specialist – Retail/Service Backgrounds Welcome

Engineering Manager

• Lead customer-facing Agentic AI product leveraging LLMs, agents, and internal APIs.
• Work with partners like OpenAI to integrate Jerry.ai services into the ChatGPT app.
• Define prompt consolidation and migration strategy.
• Own the technical prioritization queue and chatbot prioritization.
• Track emerging technology and manage the OpenAI relationship.

Technical Product Manager, AI Engineering – Systems

• Lead the customer-facing Agentic AI product leveraging LLMs, agents, and internal APIs.
• Define the strategy for migrating prompts onto a unified platform.
• Own the technical prioritization queue for chatbot projects.
• Track voicebot and computer use for investment decisions.
• Collaborate with engineering, data, operations, and other teams on execution.

Senior Technical Product Manager, AI Engineering – Systems

Artificial Intelligence

• Lead end-to-end development for our AI platform and customer experiences, from initial roadmap to rollout.
• Partner with engineers to design prompt strategies, evaluation frameworks, and guardrails—balancing latency, cost, and accuracy.
• Serve as the technical translator between engineering and the broader organization, establishing AI best practices and platform standards.
• Drive systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation.
• Work with partners at OpenAI to evaluate and deploy the next generation of voice models and workflow automation.

Senior Manager, AI Agents, Automation

Business Operations

• Partner with marketing, product, and business development teams to integrate customer performance insights into user and partner acquisition strategies
• Lead the design, execution, and analysis of A/B experiments on new and existing features, extracting key insights to inform product and business strategies
• Define, understand, and test levers to drive profitable and scalable user acquisition and partnership growth
• Identify opportunities to automate manual processes and optimize operational efficiency