Aynsley Wilton
Richmond,VA
Summary
Strategic and results-driven Chief of Staff with over 24 years of administrative office experience providing high-level support to global and domestic CEOs and executive leadership teams. Adept at driving operational efficiency, optimizing executive productivity, and implementing strategic initiatives. Experienced in executive advisory, project management, cross-functional team leadership, and organizational development. A resourceful problem solver with a keen ability to manage priorities, facilitate decision-making, and enhance corporate governance. Known for discretion in handling confidential matters, superior communication skills, and a proactive approach to business operations.
Overview
10
10
years of professional experience
1
1
Certification
Work History
Chief of Staff to the CEO
Hosted Backbone, LLC
Richmond, VA
09.2023 - Current
- Serve as a strategic advisor and right-hand to the CEO, driving key initiatives and organizational priorities
- Oversee executive operations, managing high-level communications, scheduling, and cross-functional coordination
- Lead strategic planning efforts, ensuring alignment between business objectives and operational execution
- Facilitate decision-making processes by conducting research, analyzing data, and preparing key insights
- Enhance internal processes to improve efficiency and productivity across leadership functions
- Also helped assist the company with organizing and restructuring administrative departments, such as Human Resources, Sales, Accounting, Employee Benefits, and Payroll
- Streamlined office processes and procedures to boost profits and productivity and facilitate continuous improvements.
- Trained employees on best practices and protocols while managing teams to maintain optimal productivity.
- Analyzed data trends to identify areas of improvement within the organization.
National Office Operations Manager / Senior Executive Administrative Assistant, Global CEO, COO, CFO, and U.S. Managing Director/ Chief of Staff to Global CEO
Ippon Technologies, LLC
Richmond, VA
11.2016 - 07.2023
- Progressive Leadership & Executive Support: Initially hired in 2016 as the Richmond Office Manager, and was quickly promoted to National Office Manager to develop and hire Ippon departments, company policies, handbooks, and procedures while building and training key departments, including Sales, Human Resources, Payroll, Accounting, and Employee Benefits
- Established a strong working relationship with the Global CEO, leading to cross-functional experience in all company departments
- Helped the CEO find and build new national offices, as well as hire and train at the following Ippon USA offices: Washington, D.C
- (2017), New York, NY (2018), and Atlanta, GA (2019)
- I served as Executive Administrative Assistant to global executives, including the CEO, COO, CFO, CTO, and U.S
- Managing Director
- I was ultimately promoted to Chief of Staff to the Global CEO in Paris, France
- Our global president believed that in order to truly understand a business, you must wear multiple hats and learn all departments and their key functions
- Acted as Chief of Staff to CEO, overseeing strategic initiatives, business operations, and executive priorities
- Managed executive-level communications, aligning organizational goals with leadership directives
- Provided advisory support, tracking key performance indicators and ensuring accountability across leadership
- Led cross-functional projects, coordinating with department heads to drive business efficiency
- Managed national and international travel, ensuring seamless execution of leadership engagements
- Established and optimized internal policies to align with organizational objectives and enhance operational effectiveness
- Directed company-wide events, leadership retreats, and high-profile corporate gatherings
- Provided financial oversight, managing executive budgets, approvals, and expense reporting
- Implemented company-wide process improvements to enhance workflow, productivity, and compliance
- Fully managed 7 executive calendars (globally)
- Approved all employee PTO requests and calendars
- Managed and booked all company employee travel
- Organized company events such as Exec-Tech dinners, AWS Conferences and Seminars, AWS/Snowflake Events, and all company travel bookings, both domestic and international
- Identified and resolved unauthorized, unsafe, or ineffective practices
- Directed initiatives to improve work environment, company culture and overall business strategy
- Introduced software tools and process improvements
- Traveled to over five national locations a month to manage each office and perform review administration policies and processes
- Office management responsibilities included: member of senior leadership team, payroll, monthly invoicing, bookkeeping (both AP/AR), margin reviews, managing national expense reporting, onboarding, and off-boarding of new hires, and working and maintaining relationships with our banks and accountants
Senior Executive Administrative Assistant
Heritage Wealth Advisors
Richmond, VA
05.2016 - 10.2016
- Acted as a strategic partner to the CEO, managing high-priority initiatives and executive-level projects
- Provided board liaison support, scheduling meetings, preparing agendas, and documenting key discussions
- Provided direction and priority standards for CEO's phone calls, voicemail, mail, and email using expert judgment and knowledge of firm's policies and procedures while exercising independent discretion when responding to inquiries
- Managed stakeholder relationships, serving as a key point of contact for executive leadership
- Oversaw corporate events, managing logistics and coordinating high-profile engagements
- Developed and implemented operational strategies to optimize efficiency and effectiveness
- Completed a broad variety of administrative tasks for President, CEO, as well as other executive staff members while managing 13 active calendars of appointments
- Arranged and scheduled complex meetings, initiate, and respond to requests for scheduled time, maintain current and accurate calendars to ensure efficient scheduling all while minimizing conflicts
- Prepared, reconciled, and completed monthly detailed expense reports in a timely and accurate manner
- Received and initiated extensive and regular outside contacts with executives and board members of other companies, internal departments, regulators, elected representatives, charitable boards, foundation boards, and customers
- Served as President's administrative liaison to Foundations
- Facilitated communication, planned events, distributed information, draft meeting agendas, schedule meetings around board member's schedules and often record minutes of meetings
- Supervised junior level staff including one other executive administrative assistant as well as firm's receptionist
- Coordinate weekly administrative pull-up meetings to ensure internal processes and systems are appropriately being covered
- Produced accurate office files, updated spreadsheets, and crafted presentations to support executives and boost team productivity
- Efficiently managed media distribution (TV, press), lead generation, advertising campaigns, sales promotion campaigns, publisher relations and collaborative ventures
- Planned and organized firm's company and gold client events from company and client holiday parties, employee team building days, firm golf tournaments, as well as outside corporate events and sponsorships
- Some of these include Holiday parties at the Virginia Cliffe Inn, Excel for Excellence Celebrity Waiter Event at the Quirk Hotel, and the Dominion Virginia Power Classic Golf Tournament
- Updated spreadsheets and created presentations to support executives and boost team productivity
- Implemented updated policies and practices for organization and monitored effect
- Wrote and enforced administrative procedure plans to reduce errors and prevent process delays
- Cultivated strong relationships with external partners to foster collaboration and maximize resources
Senior Executive Administrative Assistant, CEO
MassMutual of Greater Richmond
Glen Allen, VA
04.2015 - 05.2016
- Served as a trusted advisor and strategic partner to the General Agent, managing high-level administrative functions, business operations, and executive initiatives to drive organizational success
- Provided executive-level support, including calendar management, meeting coordination, travel arrangements, and confidential correspondence, ensuring seamless daily operations
- Acted as a key liaison between the General Agent and internal stakeholders, streamlining communication and facilitating collaboration across departments
- Managed special projects, business development initiatives, and operational strategies to enhance efficiency and optimize workflow
- Oversaw office operations, budget tracking, and resource allocation, ensuring fiscal responsibility and operational effectiveness
- Conducted in-depth research, prepared executive reports, and developed presentations to support strategic decision-making
- Led the coordination of high-impact meetings, including agenda development, stakeholder engagement, and post-meeting follow-ups
- Maintained discretion and confidentiality while handling sensitive company information and personnel matters
- Fostered a positive corporate culture by assisting with talent development initiatives, onboarding processes, and employee engagement programs
- Demonstrated exceptional problem-solving skills and adaptability in a fast-paced, high-pressure environment
Education
Bachelor of Business Administration - Business Administration and Management, English, Journalism
Old Dominion University
Norfolk, Virginia05.2007
Associate in Applied Science - Business Administration
Tidewater Community College/University of Virginia
Virginia Beach, VA05.2005
High School Diploma -
The Steward School
Richmond, Virginia05.2003
Skills
- Executive Advisory & Decision Support
- Strategic Planning & Execution
- Business Administration & Operations
- Cross-Functional Team Leadership
- Process Improvement & Change Management
- Corporate Governance & Compliance
- High-Level Calendar & Schedule Management
- Board and Stakeholder Relations
- Budgeting and Financial Oversight
- Travel Coordination and Expense Management
- Office & Event Management
- Communication & Relationship Building
- Organizational development
- Meeting facilitation
- Ethical leadership
- Business needs identification
- Attention to detail
- Time management abilities
- Multitasking abilities
- Innovation management
Certification
- Licensed Notary, VA
- Leadership & Executive Coaching Certification, 2019
- Project Management Professional (PMP) Training, 2023
- SHRM-Certified Professional (SHRM-CP), 2024
Professionaldevelopmentandaffiliations
- Chief of Staff Network, Membership
- French American Alliance, Membership
Affiliations
A dynamic and strategic Chief of Staff with a proven ability to balance executive priorities, organizational efficiency, and personal development. Beyond driving cross-functional initiatives and fostering high-performing teams, I actively engage in mentorship, philanthropy, and continuous learning to enhance both professional and personal growth. Passionate about leadership development, community involvement, and maintaining a well-rounded lifestyle through fitness, travel, and creative pursuits, I bring a balanced perspective that fosters innovation, collaboration, and sustainable success
Timeline
Chief of Staff to the CEO
Hosted Backbone, LLC
09.2023 - Current
National Office Operations Manager / Senior Executive Administrative Assistant, Global CEO, COO, CFO, and U.S. Managing Director/ Chief of Staff to Global CEO
Ippon Technologies, LLC
11.2016 - 07.2023
Senior Executive Administrative Assistant
Heritage Wealth Advisors
05.2016 - 10.2016
Senior Executive Administrative Assistant, CEO
MassMutual of Greater Richmond
04.2015 - 05.2016
Bachelor of Business Administration - Business Administration and Management, English, Journalism
Old Dominion University
Associate in Applied Science - Business Administration
Tidewater Community College/University of Virginia
High School Diploma -
The Steward School
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