Staff Product Manager

Jobtailor; California (MO); On-site; USD 120,000 - 180,000; Full time

Job summary

Jobtailor is seeking a seasoned Product Manager to own the full lifecycle of concurrent software projects in insurance and digital services. You will collaborate with engineering and design across customer-facing experiences, operations tooling, automation, and integrations.

You will prototype rapidly using AI tools, maintain clear documentation, and define success metrics. You’ll report directly to the CEO and drive 6–12 month visions that balance data with stakeholder feedback.

Qualifications

• At least 7+ years of product management experience in software or digital services.
• At least 2 years operating in a startup environment.
• Experience launching AI/ML enabled products.
• Proven cross-functional team management.
• Data-driven decision making.
• Office 2–4 days per week in SF Bay Area or Boston.

Responsibilities

• Own the full product lifecycle of concurrent projects across insurance and digital services platforms.
• Work with engineering and design across customer-facing experiences, internal operations tooling, automation, and integrations.
• Use AI-assisted tools to rapidly prototype and validate concepts.
• Maintain documentation so stakeholders understand what is being built, why, and when.
• Define clear success metrics and ensure accountability across teams.
• Combine quantitative data analysis with qualitative feedback to inform product decisions.
• Collaborate across the business to align product development with strategic objectives.
• Ensure products comply with local and national regulations and data security best practices.
• Report directly to the CEO.
• Ship products, measure health and success, build stakeholder relationships, and establish 6–12 month visions.

Skills

Product management

AI/ML tech

Cross-functional leadership

Data analysis

MVP prototyping

Tools

Claude

Replit

Lovable

Job description

• Own the full product lifecycle of concurrent projects across insurance and digital services platforms
• Work with engineering and design counterparts across customer-facing experiences, internal operations tooling, automation, and integrations
• Use AI-assisted tools such as Claude, Replit, and Lovable to rapidly prototype and validate concepts
• Maintain documentation so stakeholders understand what is being built, why, and when
• Define clear success metrics and ensure accountability across teams
• Combine quantitative data analysis with qualitative customer and stakeholder feedback to inform product decisions
• Collaborate across the business to align product development with strategic objectives
• Ensure products comply with local and national regulations and data security best practices
• Report directly to the CEO
• Ship products, measure product health and success, build stakeholder relationships, and establish 6–12 month visions

Requirements

• At least 7+ years of product management experience in software or digital services
• At least 2 years operating in a startup environment
• Strong preference for experience building both operational product and consumer-facing product
• Strong preference for experience launching products incorporating AI and ML technologies
• Demonstrated success managing cross-functional teams and complex roadmaps
• Tangible track record with quantifiable results directly impacting the top or bottom line
• Critical and strategic thinking to build the right product
• Technical and detailed execution to build the product right
• Written and verbal communication skills across key stakeholders
• Ability to seek out and leverage data for informed decisions
• Experience prototyping and building lightweight MVPs using AI tooling
• Ability to work in the office 2–4 days per week
• Ability to work from either the San Francisco Bay Area or Boston office

Core Competencies

Demonstrates extensive product management experience with a focus on both operational and consumer-facing products, leveraging AI and ML technologies. Proven ability to manage cross-functional teams, define success metrics, and align product development with strategic objectives.

Highest-signal resume keywords

• Product Management Experience
• AI and ML Technologies
• Cross-Functional Team Management
• Quantitative Data Analysis
• Prototyping and MVP Development

Hard Skills

• Product Lifecycle Management
• Data Analysis
• Roadmap Management
• Success Metrics Definition
• AI Tooling Prototyping

Soft Skills

• Critical Thinking
• Strategic Thinking
• Written Communication
• Verbal Communication

Industry Keywords

• Insurance
• Digital Services
• Startup Environment
• Data Security Compliance

Tools & Technologies

• Claude
• Replit
• Lovable