Digital Insurance LLC · Remote

Chief of Staff - Product at Digital Insurance LLC — Remote

Full-timeRemote$70,000–$80,000/yearPosted 2026-07-16Apply on Workday
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Full job description

Our Newest Opportunity:

This role is a unique opportunity for an ambitious and forward-thinking Chief of Staff who is interested in growing beyond traditional executive support and into the world of Product, Operations, and AI-driven workflows.

Initially serving as the trusted right hand to the Chief Product Officer, this individual will play a critical role in keeping the product organization operating efficiently and effectively, while gaining direct exposure to product strategy, roadmap planning, cross-functional execution, and executive decision-making.

Over time, this role is designed to evolve. The individual will have the opportunity to take on increasing ownership of product operations, strategic initiatives, workflow optimization, and product lifecycle activities — including leveraging emerging AI tools to improve how the organization operates. This position offers a clear growth path into Product Operations, Product Analyst, or Chief of Staff roles.

Essential Duties and Responsibilities

Administrative & Executive Support

  • Manage a complex executive calendar, meetings, travel, expenses, and confidential communications for the Chief Product Officer
  • Prioritize competing requests, proactively anticipate needs, and ensure the CPO is prepared for meetings, decisions, and strategic initiatives
  • Coordinate executive staff meetings, product leadership meetings, off-sites, and cross-functional planning sessions
  • Manage meeting logistics, prepare agendas, capture action items, and drive follow-up across stakeholders
  • Handle sensitive information with professionalism, discretion, and sound judgment

Product Operations & Strategic Exposure

  • Partner closely with the CPO to support day-to-day product organization operations and strategic initiatives
  • Assist in coordinating product roadmap discussions, planning sessions, and cross-functional communication across Product, Engineering, Design, and Business teams
  • Track action items, strategic initiatives, and key deliverables to ensure priorities continue moving forward
  • Prepare presentations, executive updates, reports, and documentation supporting product leadership
  • Gain exposure to product planning, customer initiatives, product lifecycle activities, and organizational priorities while gradually assuming additional ownership over operational and analytical responsibilities
  • Support special projects and process improvement initiatives that improve visibility, execution, and operational efficiency across the product organization

AI, Automation & Workflow Optimization

  • Identify opportunities to improve operational efficiency through automation and AI-enabled tooling
  • Leverage modern tools (e.g., workflow automation platforms, copilots, internal tools) to streamline repetitive tasks, reporting, and communication workflows
  • Experiment with and introduce new approaches to organizing information, tracking initiatives, and enhancing team productivity
  • Partner with stakeholders to improve how information is captured, synthesized, and distributed across the product organization

Qualifications, Skills, and Requirements:

  • 3+ years supporting C-level executives or senior leaders in a fast-paced, dynamic environment
  • Exceptional organizational, communication, and time management skills
  • Highly proactive with the ability to anticipate needs and operate with minimal direction
  • Strong attention to detail with excellent follow-through
  • Comfortable managing confidential information with the highest level of integrity
  • Demonstrated ability to coordinate multiple priorities while working across diverse stakeholder groups
  • Naturally curious with a strong interest in technology, product development, and business strategy
  • Interest in leveraging AI tools or automation to improve workflows and productivity
  • Strong written communication and presentation development skills
  • Advanced proficiency with Microsoft Office; experience with collaboration and project management tools is a plus

Education, Training and Experience:

  • Bachelor’s Degree preferred
  • Experience supporting Product, Technology, Engineering, or Software executives is highly desirable
  • Exposure to Product Management, Product Operations, Agile environments, project coordination, business analysis, or strategic operations is a plus
  • Demonstrated interest or experience experimenting with AI tools, workflow automation, or building efficiency systems (professional or personal)
  • Candidates seeking long-term growth into Product Management, Product Operations, Chief of Staff, or strategic operational roles are encouraged to apply

Career Growth

This is not intended to be a long-term traditional Chief of Staff role. The right individual will be mentored by the Chief Product Officer and, over time, will have the opportunity to grow into broader strategic, product, and operational responsibilities.

The typical base pay range for this role nationwide is $70,000 to $80,000 per year.

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