Chief of Staff - Product

Digital Insurance LLC; Massachusetts; Hybrid; USD 70,000 - 80,000; Full time

Benefits offered by this job

Health benefits

Retirement plan

Paid time off

Learning & development programs

Expense reimbursement

Job summary

Digital Insurance LLC seeks a Chief of Staff to the Chief Product Officer, blending executive support with product operations. The role offers exposure to product strategy, automation initiatives, and cross-functional collaboration across Product, Engineering, Design, and Business teams.

You will manage calendars, coordinate strategic initiatives, and prepare leadership updates while gradually assuming more ownership over operational and analytical duties.

Qualifications

• 3+ years supporting C-level executives or senior leaders in a fast-paced environment.
• Strong organizational, communication, and time-management skills.
• Highly proactive with ability to anticipate needs and operate with minimal direction.
• Attention to detail with excellent follow-through.
• Experience handling confidential information with integrity.

Responsibilities

• Manage the Chief Product Officer’s calendar, meetings, travel, expenses, and confidential communications.
• Prioritize requests, anticipate needs, and prepare the CPO for strategic initiatives.
• Coordinate executive staff and product leadership meetings and cross-functional planning sessions.
• Prepare agendas, capture action items, and drive follow-up across stakeholders.
• Support product planning and cross-functional communication across Product, Engineering, Design, and Business teams.
• Identify opportunities to improve workflows via automation and AI-enabled tooling.

Skills

Executive support

Calendar management

Project coordination

Stakeholder management

Communication

AI tools interest

Education

Bachelor’s Degree

Experience supporting Product/Tech executives

Tools

Microsoft Office

Asana

Job description

Role Overview

Chief of Staff to the Chief Product Officer – a multifaceted position focused on product strategy, operations, AI‑driven workflow optimization, and executive support. The role will evolve into broader product operations and strategic responsibilities with clear growth paths into Product Operations, Product Analyst, or Chief of Staff roles.

Responsibilities

Administrative & Executive Support

• Manage the Chief Product Officer’s complex calendar, including meetings, travel, expenses, and confidential communications.
• Prioritize competing requests, proactively anticipate needs, and ensure the CPO is prepared for strategic initiatives.
• Coordinate executive staff meetings, product leadership meetings, off‑sites, and cross‑functional planning sessions.
• 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 remain on track.
• 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

• 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.
• 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 & 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).

Benefits & Compensation

• Base pay range: $70,000 to $80,000 per year (dependent on skills, experience, and location).
• Variable compensation, commission, and/or annual bonus based on performance and company results.
• Health, wellbeing, retirement, and other financial benefits.
• Paid time off, overtime pay for non‑exempt employees, and robust learning and development programs.
• Reimbursement of job‑related expenses per company policy and employee perks and discounts.

Equal Employment Opportunity

OneDigital is an equal opportunity employer. We celebrate diversity and are committed to cultivating and preserving a culture that emphasizes equity and inclusion. We provide equal employment opportunities to all employees and applicants for employment regardless of veteran status, uniformed service member status, race, color, religion, sex, sexual orientation, gender identity, age (40 and over), pregnancy, national origin or ancestry, citizenship or immigration status, physical or mental disability, genetic information, or any other category protected by federal, state or local law.

For applicable candidates, OneDigital complies with local Fair Chance Ordinances and will consider qualified applications with arrest or conviction records for employment. We also provide a copy of the Federal EEO poster here.