What are the responsibilities and job description for the Executive Assistant to the CEO position at Kelly Benefits?
Brief Description
About Kelly Benefits –
Kelly & Associates Insurance Group, Inc., a Kelly Benefits company, is one of the nation’s largest employee benefit administrators, brokers, payroll providers and consultants.
We’re committed to helping businesses navigate the intricacies of insurance, benefits, payroll, retirement and other offerings and services, while saving them time and money.
Kelly Benefits Delivers High Quality, Cost-effective, Integrated Solutions Through
Our mission is rooted in helping people thrive while honoring our commitment to doing the right thing, treating others with respect, and fostering meaningful relationships. As a family-owned organization, we value trust, loyalty, stewardship, and a servant-leadership mindset.
We are seeking an exceptional Executive Assistant to serve as a trusted partner to our CEO and family leadership team. This is a highly visible role requiring discretion, professionalism, adaptability, and a commitment to excellence.
The Executive Assistant to the CEO, Frank Kelly III, serves as the primary administrative, operational, and project management partner to the CEO. This individual will provide high-level support for business operations, strategic initiatives, executive communications, family-related responsibilities, community involvement, and special projects.
This role requires exceptional organizational abilities, sound judgment, rapid decision-making, confidentiality, and the ability to anticipate the needs of a dynamic executive and family-owned business environment. The ideal candidate is highly responsive, thrives in a fast-paced setting, and is comfortable balancing corporate responsibilities with family office support.
Key Responsibilities
The Ideal Candidate Will Possess
This role is located at our Corporate Headquarters at 1 Kelly Way in Sparks, MD 21152.
Our standard office hours are Monday – Friday 8:15am – 5:00pm.
The Successful Candidate Must Be Comfortable With
Why Join Us?
This is a unique opportunity to work directly alongside a CEO and family leadership team that has spent over five decades building a respected organization rooted in faith, strong values, and community impact. You'll become a trusted advisor, strategic partner, and key contributor to the continued success of a company that believes people matter most.
Working here means you’ll be part of a mission-driven team that values growth, collaboration, and service excellence. You’ll gain the knowledge, mentorship, and real-world experience needed to build a strong professional foundation—and a career you can be proud of.
Kelly Benefits is committed to treating our People with dignity and respect, dealing with them honestly, compensating them fairly, and providing quality benefits and opportunities to develop their full potential.
If you are a highly organized, exceptionally trustworthy professional who thrives in a fast-paced executive environment and is passionate about supporting mission-driven leadership, we would love to hear from you.
Apply today and become part of a legacy built on faith, family, service, and excellence.
Our Values
We Seek Individuals Who
We offer a robust benefits package including:
📈 401K with Match
🏖️ Paid Time Off
🧑🧑🧒 Paid Parental Leave
🏥 Medical, Dental, Vision, Life, Disability & other voluntary insurance options
💪 On-site Fitness Center
☕️ Cold Brew & Coffee on tap
🌸 Campus Walking Path
🙏🏼 Corporate Chaplain & Monthly Devotion
🥒 Pickle Ball Courts on Campus
About Kelly Benefits –
Kelly & Associates Insurance Group, Inc., a Kelly Benefits company, is one of the nation’s largest employee benefit administrators, brokers, payroll providers and consultants.
We’re committed to helping businesses navigate the intricacies of insurance, benefits, payroll, retirement and other offerings and services, while saving them time and money.
Kelly Benefits Delivers High Quality, Cost-effective, Integrated Solutions Through
- An incredible team of dedicated professionals. Our set of business values called “The Kelly Way” inspires, guides and drives us to serve our clients with excellence.
- Efficient processes, tools and technology. We’re dedicated to delivering cost-effective efficiencies.
- High-integrity alliances with the finest health, life, disability, dental and vision carriers, suppliers and brokers.
Our mission is rooted in helping people thrive while honoring our commitment to doing the right thing, treating others with respect, and fostering meaningful relationships. As a family-owned organization, we value trust, loyalty, stewardship, and a servant-leadership mindset.
We are seeking an exceptional Executive Assistant to serve as a trusted partner to our CEO and family leadership team. This is a highly visible role requiring discretion, professionalism, adaptability, and a commitment to excellence.
The Executive Assistant to the CEO, Frank Kelly III, serves as the primary administrative, operational, and project management partner to the CEO. This individual will provide high-level support for business operations, strategic initiatives, executive communications, family-related responsibilities, community involvement, and special projects.
This role requires exceptional organizational abilities, sound judgment, rapid decision-making, confidentiality, and the ability to anticipate the needs of a dynamic executive and family-owned business environment. The ideal candidate is highly responsive, thrives in a fast-paced setting, and is comfortable balancing corporate responsibilities with family office support.
Key Responsibilities
- Serve as the trusted right-hand partner to the CEO, managing priorities and daily operations.
- Manage a complex and ever-changing executive calendar, balancing business, community, board, philanthropic, family, and personal commitments.
- Handle executive communications, including email correspondence, rapid dictation transcription, phone calls, text communications, LinkedIn messaging, and written communications.
- Draft, edit, proofread, and prepare reports, presentations, correspondence, speeches, meeting materials, and executive communications.
- Maintain confidential files, records, contact databases, and executive documents.
- Coordinate travel arrangements, accommodations, transportation, itineraries, and special travel requests for the CEO and family members.
- Manage expense reporting, credit card reconciliations, invoices, and executive administrative functions.
- Serve as a professional representative of the CEO and Executive Office.
- Coordinate personal and family scheduling, events, appointments, travel, correspondence, and special projects.
- Manage family-related communications and logistics with professionalism and discretion.
- Assist with personal administrative matters, household coordination, special events, and family initiatives as requested.
- Support family philanthropic, community, faith-based, and charitable activities.
- Lead and coordinate strategic projects on behalf of the CEO.
- Develop project plans, timelines, action items, and follow-up processes.
- Monitor progress and ensure projects remain on track and aligned with organizational priorities.
- Coordinate efforts across multiple departments and stakeholders.
- Manage project tracking systems and reporting tools.
- Coordinate Executive and Senior Leadership Team meetings.
- Prepare agendas, presentations, reports, minutes, and follow-up action items.
- Manage meeting logistics including conference rooms, virtual meeting technology, catering, guest accommodations, and executive events.
- Support leadership retreats, strategic planning sessions, community events, and company functions.
- Collaborate closely with Marketing, Communications, HR, Finance, IT, and other departments.
- Build strong relationships with employees, clients, vendors, board members, community leaders, and family representatives.
- Act as a communication liaison between the CEO and internal/external stakeholders.
- Ensure executive communication reflects the organization's mission, values, and professional standards.
- 8 years of executive-level administrative support experience.
- Experience supporting a CEO, business owner, entrepreneur, executive leader, or family office preferred.
- Proven success managing multiple priorities in a fast-paced environment.
- Ability to handle highly confidential information with impeccable discretion.
- Advanced Microsoft Office skills, including Outlook, Word, PowerPoint, Excel, and Teams.
- Experience in a family-owned business environment.
- Project management experience.
- Event planning and executive meeting coordination experience.
- Experience supporting board meetings and executive leadership teams.
- Familiarity with AI productivity tools and modern workplace technologies.
The Ideal Candidate Will Possess
- Exceptional rapid dictation skills with the ability to accurately transcribe, organize, and respond to executive communications in real time.
- Outstanding written communication and professional correspondence abilities.
- Extreme attention to detail and organizational excellence.
- Strong executive presence and professionalism.
- Excellent judgment and decision-making capability.
- Ability to anticipate needs before they arise.
- Strong relationship-building skills.
- High emotional intelligence and discretion.
- Flexibility, resilience, and adaptability in changing environments.
- A servant-leadership mindset and commitment to supporting others.
This role is located at our Corporate Headquarters at 1 Kelly Way in Sparks, MD 21152.
Our standard office hours are Monday – Friday 8:15am – 5:00pm.
The Successful Candidate Must Be Comfortable With
- Flexible work hours based on executive and business needs
- Early morning meetings and responsibilities
- Occasional evening commitments
- Potential weekend availability when business, travel, family, community, or special events require support
- Being accessible and responsive during critical business situations
Why Join Us?
This is a unique opportunity to work directly alongside a CEO and family leadership team that has spent over five decades building a respected organization rooted in faith, strong values, and community impact. You'll become a trusted advisor, strategic partner, and key contributor to the continued success of a company that believes people matter most.
Working here means you’ll be part of a mission-driven team that values growth, collaboration, and service excellence. You’ll gain the knowledge, mentorship, and real-world experience needed to build a strong professional foundation—and a career you can be proud of.
Kelly Benefits is committed to treating our People with dignity and respect, dealing with them honestly, compensating them fairly, and providing quality benefits and opportunities to develop their full potential.
If you are a highly organized, exceptionally trustworthy professional who thrives in a fast-paced executive environment and is passionate about supporting mission-driven leadership, we would love to hear from you.
Apply today and become part of a legacy built on faith, family, service, and excellence.
Our Values
We Seek Individuals Who
- Lead with integrity and honesty.
- Demonstrate humility, respect, and compassion.
- Value faith, family, service, and community.
- Display professionalism and accountability.
- Treat others the way they would want to be treated.
- Maintain a positive, solutions-oriented attitude.
- Take ownership and are committed to excellence.
- Desire to make a meaningful impact in the lives of others.
We offer a robust benefits package including:
📈 401K with Match
🏖️ Paid Time Off
🧑🧑🧒 Paid Parental Leave
🏥 Medical, Dental, Vision, Life, Disability & other voluntary insurance options
💪 On-site Fitness Center
☕️ Cold Brew & Coffee on tap
🌸 Campus Walking Path
🙏🏼 Corporate Chaplain & Monthly Devotion
🥒 Pickle Ball Courts on Campus