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Home Flexible Job Board Chief of Staff - Product

$70,000–80,000/yr 69d ago

Chief of Staff - Product

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OneDigital

MA

Full-time Permanent Remote

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Summary

Provide high-level administrative support to the Chief Product Officer, including calendar and travel management. Gradually transition into product operations by optimizing workflows using AI tools and supporting strategic product initiatives.

Job Description

Are you looking to accelerate your career without having to hide your authentic self - a place where you can be you? A career that’s making a bigger impact on the world?  At OneDigital, we are on a mission to help people do their best work and live their best lives.  From the services we offer to the way we show up for each other each day, we are fueling dreams, achieving big goals, and embracing each other’s truest selves.

We understand that pursuing a new job is a big deal.  Maybe you’re afraid you won’t fit in.  Well, here’s the good news.  For us, the days of “fit in to get in” are over and being different is not a barrier to getting ahead. Greatness comes in all shapes, sizes, colors, and experience levels. If you are looking for a people-first culture that is wired for growth, driven to serve, and totally committed to having your back, give us a shot. Your best life awaits.

Must be eligible to work in the United States without the need for work visa or residency sponsorship.

We kindly ask that external recruiters, agencies, and search firms do not contact our hiring managers or employees directly regarding open positions. All candidate submissions must go through our official application process and must be made aware to our internal Talent Acquisition team to verify candidate ownership.

Unsolicited resumes or candidate profiles sent to OneDigital without a prior signed agreement will be considered the property of OneDigital. In such cases, OneDigital reserves the right to pursue and hire those candidates without any financial obligation to the agency or recruiter.

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.

Your base pay is dependent upon your skills, education, qualifications, professional experience, and location. In addition to base pay, some roles are eligible for variable compensation, commission, and/or annual bonus based on your individual performance and/or the company’s performance. We also offer eligible employees health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non-exempt employees, and robust learning and development programs. You will receive reimbursement of job-related expenses per the company policy and may receive employee perks and discounts.

To learn more, visit: www.onedigital.com/careers

OneDigital is an equal opportunity employer. Not only as a matter of standard, but to honor and celebrate our differences. We believe that the power of ONE starts with you. We are committed to cultivating and preserving a culture that celebrates diversity, insists on equity and inclusion, and connects us. Ensuring our people feel seen, valued, respected, and supported is fundamental to our core values and business goals.

OneDigital provides equal employment opportunities to all employees and applicants for employment regardless of their: veteran status, uniformed servicemember status, race, color, religion, sex, sexual orientation, gender identity, age (40 and over), pregnancy (including childbirth, lactation and related medical conditions), national origin or ancestry, citizenship or immigration status, physical or mental disability, genetic information (including testing and characteristics) or any other category protected by federal, state or local law (collectively, “protected characteristics”). A copy of the Federal EEO poster is linked here.

Pursuant to local Fair Chance Ordinances, we will consider qualified applications with arrest or conviction records for employment. For applicable candidates, the following ordinances are linked here to inform you of your rights as an applicant:

City and County of San Francisco

City of Los Angeles

County of Los Angeles

Employment decisions shall comply with all other applicable federal, state and city/county laws prohibiting discrimination in employment. OneDigital complies with all criminal history inquiry [or ‘ban the box’] laws in California, Connecticut, Colorado, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New Jersey, New Mexico, Oregon, Rhode Island, Vermont and Washington.

In short, we believe in hiring the most qualified applicant for the position, regardless of background.

This posting will remain live while OneDigital is actively accepting applications. Once candidates have been selected, the posting will be removed.

OneDigital understands the immense responsibility and opportunities provided by Artificial Intelligence. We utilize advanced Artificial Intelligence [AI] technologies to enhance our recruitment process. This includes using AI to filter candidates based on their qualifications and to rediscover potential candidates from our existing applicant pool. Our AI systems help us efficiently identify the best fit for our open positions, ensuring a streamlined and effective hiring experience. However, AI does not replace the humans in our process. If you have concerns about our use of AI, you may opt out where laws allow.

If you have questions about our hiring policies and practices, we would be happy to discuss upon receiving your application. We hope to welcome you to OneDigital and look forward to hearing from you.

Thank you for your interest in joining the OneDigital team!

About the company

OneDigital

OneDigital’s team of fierce advocates helps businesses and individuals achieve their aspirations of health, success and financial security. Our insurance, financial services and HR platform provide personalized, tech-enabled solutions for a contemporary work-life experience.

Nationally recognized for our culture of caring, OneDigital’s teams enable employers and individuals to do their best work and live their best lives. More than 100,000 employers and millions of individuals rely on our teams for counsel and access to fully integrated worksite products and services and the retirement and wealth management advice provided through OneDigital Investment Advisors. Founded in 2000 and headquartered in Atlanta, OneDigital maintains offices in most major markets across the nation.

For more information, visit onedigital.com.

Founded

2000

Company size

5,001-10,000 employees

Industry

Insurance, Financial Services, HR Consulting

Org type

Privately Held

Headquarters

Atlanta, Georgia

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About the company

OneDigital

OneDigital’s team of fierce advocates helps businesses and individuals achieve their aspirations of health, success and financial security. Our insurance, financial services and HR platform provide personalized, tech-enabled solutions for a contemporary work-life experience.

Nationally recognized for our culture of caring, OneDigital’s teams enable employers and individuals to do their best work and live their best lives. More than 100,000 employers and millions of individuals rely on our teams for counsel and access to fully integrated worksite products and services and the retirement and wealth management advice provided through OneDigital Investment Advisors. Founded in 2000 and headquartered in Atlanta, OneDigital maintains offices in most major markets across the nation.

For more information, visit onedigital.com.

Founded

2000

Company size

5,001-10,000 employees

Industry

Insurance, Financial Services, HR Consulting

Org type

Privately Held

Headquarters

Atlanta, Georgia

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