Executive Operations Assistant
Chiles Enterprises is seeking a highly organized, detail-oriented Executive Operations Assistant to support
leadership within Chiles Enterprises. This role is ideal for someone who enjoys creating structure, solving
small problems before they become big ones, and providing steady, behind-the-scenes support that
helps a busy team succeed. Ninety percent of tasks will be repeatable with 10% being unique special
projects. If you take pride in accuracy, efficiency, and helping others do their best work, we’d love to talk
with you.
This is a full-time position, generally working Monday-Friday from 8:00AM-5:00PM. However, part-time
candidates will still be considered. Flexible scheduling may be available for the right candidate as we
value finding the right person more than fitting a rigid schedule.
A comprehensive benefits program is included for full-time Team Members, plus a starting pay of
$20.50-$24.50/hour depending upon experience and aptitude.
Chiles Team Members enjoy up to four weeks per year of earned paid time off, Anthem HealthKeepers
health insurance for their families (with the company paying 100% of the Team Member's monthly cost
over time), a company matched 401K, and many other benefits for being a part of the Chiles Family of
Companies. (Full benefits listed below.) This position reports directly to the Chiles Management Team.
Since 2002, Chiles Enterprises has grown into a trusted, values-driven company serving Central Virginia.
We believe in supporting good people, investing in growth, sharing success, and creating systems that
help teams thrive.
We are a drug and alcohol-free workplace. All applicants must pass a pre-employment drug screening as
well as random drug screenings throughout their employment. Applicants must also pass a background
check and have an insurable driving record.
Key Responsibilities
Administrative & Financial Support
● Categorize overhead receipts and expenses in QuickBooks.
● Assist with vendor payments and expense tracking.
● Support preparation of annual budgets and financial documentation.
Payroll & HR Support
● Manage weekly direct deposit payroll processing.
● Assist with annual insurance audits and health insurance documentation.
● Support H-2B paperwork and subcontractor packets.
Operations & Data Management
● Assist with customer contract renewals and internal checklists.
● Support annual operational projects and documentation updates.
● Maintain organized, accurate digital records across cloud-based systems.
Communication & Customer Support
● Field and respond to overflow customer emails forwarded by leadership.
● Handle routine requests with professionalism, accuracy, and care.
● Route more complex matters to the appropriate team member
What We’re Looking For
This role is best suited for someone who:
● Is very comfortable with technology, cloud-based systems, and learning new tools.
● Finds satisfaction in details being correct and complete.
● Takes pride in supporting others and helping teams succeed.
● Works well independently and manages tasks proactively.
● Thrives in a fast-paced environment with recurring responsibilities.
Qualifications
● Prior experience in administrative, executive assistant, or operations support roles preferred.
● Strong working knowledge of Microsoft 365, Google Workspace, or similar cloud-based tools.
● Experience with QuickBooks or accounting support is a plus.
● Excellent written and verbal communication skills.
● High level of discretion and professionalism.
Team Member Benefits
At Chiles Enterprises, we understand the value of investing in our Team Members, which is why we
provide a comprehensive set of benefits to supplement our Team Members’ regular wages:
● Competitive compensation
● Anthem Healthkeepers medical insurance with an initial 50% of the Team Member’s and
qualifying dependents’ cost paid by Chiles Enterprises
● An additional 3% of Team Member medical insurance assistance for each year of employment,
leading to eventual 100% paid medical insurance.
● AFLAC supplemental insurance
● An initial 5 days paid vacation after 9 months of employment and up to 18 days paid vacation
after 48 months of employment
● 401K retirement with 3% annual company match after 90 days of employment
● Four paid personal days per year
● Life insurance available immediately after hire
● "Spin the Wheel" Loyalty Appreciation gifts (a $300-$400/yr. value): Red Wing Boot 30%
discount, 50% gym membership cost share, $200/yr. counseling benefit, product purchases 5%
above wholesale cost for personal use, $600/person referral program, $5,998 in continuing
education incentives.
Why Join Our Team?
Chiles Enterprises is a vision-driven, rapidly growing company that is always looking for motivated and
energetic people to join our team.
Since our beginning in 2002, Chiles Enterprises has become an industry-leading company focused on
assisting our neighbors, providing quality service, and investing in the growth of good people on our
team. As a result, we now serve thousands of satisfied clients through design, installation, and
maintenance of landscaping, hardscaping, lawn care, and excavation projects throughout the Louisa,
Lake Anna, and Charlottesville markets. A large portion of our clientele includes high-end residential
properties, where we design, install, and maintain uniquely beautiful outdoor spaces.
Here are some of the workspace benefits we can offer qualified candidates:
● A professional, friendly, diverse, and fun work environment
● A positive company culture with Christian-led management
● A clean and organized facility with state-of-the-art equipment
● A clear path for company growth and career advancement
● A commitment to your professional growth
Chiles Enterprises also believes in “Success Sharing.” If you are a dedicated Team Member that helps our
company grow and provide exceptional services to our clients, we want to share our company success
and profitability with you.
What Truly Sets Us Apart
1. Quality People: Our awesome crew prides themselves on incorporating the best industry
practices and the newest technologies to produce top-quality results.
2. Clear Communication: Effectively and efficiently serving our customers drives our every action.
To reach that goal and provide our customers with ultimate peace of mind, we provide clear and
consistent communication throughout all levels of our company.
3. Christ is our CEO: We are guided by prayer and a personal relationship with Jesus Christ. We
declare all our success in Him and strive to honor Him in all of our relationships.
Chiles Enterprises Core Values
We Trust, We Own, and We Synergize to create a substantial impact in our neighbors’ stories while living
out our personal and collective values.
We Serve at the Speed of Trust - Secondly only to loving God, we are to love our neighbor as we love
ourselves. Trust is established, stewarted, and measured by the unwavering respect, integrity, and
honesty, we have for ourselves and each other. We lovingly listen, lead, and serve because we care.
We Own the Details - We strengthen the trust established in our relationships by strategic planning,
precise action, and intentional reflection. As individuals, we take personal responsibility for the small
pieces of the greater end result. Our commitment to the details reflects the order and passion of our
values.
We are Synergized by Our Purpose - Individual details are aligned and synergized as a team to exceed
expectations. Our comprehensive, intentional, and unique culture is fueled by embracing change and
owning the outcomes. We exceed expectations by pioneering innovation, respecting diversity, and
always aiming towards our collective purpose.
How to Apply:
Simply navigate to the Chiles Enterprise Employment Opportunity portal at
www.chilesenterprises.net/employment to fill out and submit your online application. (There is also an
option to download and print out a hard copy if you prefer to mail or hand-deliver your application.
Mailing Address: Chiles Enterprises, 845 Ellisville Dr., Louisa, VA 23093
Email Address: chilesjobs@gmail.co