Senior AI-Driven Product Manager — Startup & Ops

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

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.