Chief Administrative Officer Jobs in Massachusetts

INTRODUCTION

First Help Financial is a fast-growing and culturally diverse company in the U.S. We provide auto loans to the underserved and care for our customers and partners with exceptional service. Through flexible financing options and tri-lingual support, we offer consumers an easier way to finance their first car. We lend to and support our portfolio which has consistently grown 30%+ each year over the last nine years.

Here you will find hard-working colleagues who come from over 20 countries. We hold ourselves to the highest standards of professionalism but also enjoy our work. Our culture and benefits are geared towards making you successful in life and comfortable at work.

Your Title: Associate Chief of Staff

Our Location: Remote anywhere within the U.S with the expectation to travel to our headquarter office located at 160 Gould Street, Suite 100, Needham, MA 02494 at least 6 times per year

You Report To: Vice President, People Operations (dotted line report to other executives)

Compensation: Competitive starting base salary of $102,000 or more dependent on experience plus bonus!

ABOUT THE OPPORTUNITY

First Help Financial, voted and certified as a “Great Place to Work” by our workforce for over five years in a row, is adding an Associate Chief of Staff to our leadership team to accommodate our remarkable growth! As the Chief of Staff, you will work closely with senior leadership, with upward management support, proactively guiding them with deadlines, helping plan structure and cadence of leadership meetings/communications, and embracing AI and technology to drive efficiency, improve decision-making, and scale the effectiveness of our leadership team.

We seek someone who thrives in a dynamic environment, working in a fast-paced company in an evolving environment who is comfortable taking on executive assistant duties while helping executives stay organized, prepared, and on pace.

You embrace new challenges and opportunities every day, contributing to our purpose-driven mission by supporting the leadership team and helping build a brighter financial future for our customers. This role is ideal for someone who brings the polish, discretion, and responsiveness of an exceptional Executive Assistant, paired with the initiative, business judgment, and operational discipline of an Associate Chief of Staff.

WHAT YOU WILL GET TO DO:

Your duties include, but are not limited to:

Strategic Leadership & Operational Excellence

• Act as an advisor and right-hand to executives, managing upward to ensure alignment on priorities and execution
• Drive accountability across leadership teams, ensuring managers and executives meet performance goals and timelines
• Coach and elevate executive effectiveness, improving decision-making, communication, and team performance
• Lead initiatives that enhance executive performance, identifying opportunities and implementing scalable solutions
• Bring structure to ambiguity and fast-paced leadership environments, creating processes that can enable growth and efficiency
• Operate with a sense of urgency, advancing leadership priorities with timeliness and accountability
• Support company leadership transformation efforts, incorporating best practices
• Leverage AI and technology platforms at a leadership level in effort to improve efficiency through automation
• Provide solution-oriented thinking, proactively recommending improvements to our current processes and practices

Executive & Administrative Partnership

• Serve as a primary liaison on behalf of executives, managing communications with internal and external stakeholders
• Handle confidential and high-priority matters with professionalism, discretion, and strong judgment
• Manage executive calendars, meetings, and travel logistics, ensuring optimal time management and prioritization
• Prepare meeting materials, agendas, presentations, and executive briefings
• Take meeting notes and translate discussions into actionable follow-ups and deliverables
• Draft, proofread, and manage executive communications including emails, reports, and presentations
• Screen and prioritize incoming communications (emails, calls, requests)
• Maintain the operating rhythm for senior leaders, including meeting cadence, preparation, follow-ups, and communication flow
• Act as an extension of the executive team by helping leaders stay aligned, prepared, and responsive
• Help executives use tools, systems, and AI-enabled workflows to improve effectiveness and reduce administrative friction

Project & Business Operations Support

• Coordinate communication across executive teams, ensuring collaboration and clarity
• Organize and maintain documentation, reporting systems, and operational workflows
• Work with People Operations to drive the planning and implementation of annual management training initiatives

Administrative & Office Operations

• Manage expense reporting, filing systems, and documentation with accuracy and compliance
• Coordinate office logistics and vendor relationships as needed
• Assist with special projects, ad hoc requests, and occasional personal tasks for executives

WHAT YOU BRING

• 3+ years of experience supporting executives, with exposure to senior leadership or high-growth environments
• Proven ability to work with and influence high-performing executives
• Strong ability to manage ambiguity, organize chaos, and implement structure
• Exceptional organizational, project management, and planning skills
• Demonstrated ability to manage multiple priorities with a high sense of urgency
• Highly professional communicator with strong writing, interpersonal, and stakeholder management skills
• Assertive and proactive, with the confidence to challenge and influence when needed
• Tech-savvy, with proficiency in Microsoft Office (Outlook, Excel, PowerPoint, Teams) and comfort leveraging AI tools
• Problem-solving skills/mentality
• High level of discretion, confidentiality, and emotional intelligence
• Ability to work independently and comfort, taking the initiative to make important decisions when necessary

FHF BENEFITS…

• Great Perks – We offer generous salaries, competitive health, and welfare benefits (medical, dental, vision, LTD/STD, Identity theft, paid parental leave and much more), paid vacation, 401(k) match, tuition reimbursement, social activities, monthly lunches, a robust employee recognition and talent development program to enhance your career with us.
• Culture - We are believers in maintaining a healthy work-life balance. While we work hard and care deeply about our customers and partners, we want you to have room for your family, friends, and yourself.
• Growth - Company growth provides unprecedented career growth. FHF’s extraordinary year over year growth in revenue and new markets provides opportunity for you to establish and develop your career growth. We engage each employee to build a career plan that benefits everyone, and we have a proven record of investing in you.

DIVERSITY AND INCLUSION

FHF is committed to building a culture that respects and embraces all walks of life, inclusive of all genders, race, culture, age, sexual orientation, and other identities. We will make accommodations when interviewing anyone with special needs.