Crew Leader & Equipment Operator
Crew Leader & Equipment Operator
Chiles Enterprises is looking for a strong, steady leader — someone who thinks ahead, sees the details,
and takes pride in running a tight job site. This is a hands-on working crew leader role, combining
equipment operation with physical, on-the-ground work alongside the crew. While operating skid steers
and mini-excavators is part of the position, this role also requires active participation in daily labor,
jobsite setup, and project execution. If you’re the kind of leader who leads from the front, keeps projects
on schedule, holds a crew accountable, and still brings respect and encouragement to the team, this may
be the opportunity you’ve been looking for.
A comprehensive benefits program is included, plus a starting pay of $20.50-$26.50/hour depending
upon experience and aptitude. This is a full-time position, generally working Monday-Friday from
7:00AM-5:00PM. Evening/weekend work may occur in times of snow removal or natural disasters.
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. This position reports directly to the Chiles Management Team.
Job Responsibilities
The Crew Leader & Equipment Operator is a key working leadership role at Chiles Enterprises. This
Team Member is responsible for operating heavy equipment and actively performing physical, on-site
work while leading a small crew through landscape and excavation projects. Success in this role requires
precision, efficiency, and a strong work ethic — both in the operator’s seat and on the ground.
This position is best suited for someone who is organized, detail-oriented, and confident in
decision-making — a leader who can manage timelines, uphold quality standards, and keep projects
moving forward by working alongside the crew, not directing from a distance.
Equipment Operation & Field Work
● Safely and efficiently operate skid steers, mini-excavators, and related equipment for grading,
digging, material handling, and site preparation.
● Transition seamlessly between operating equipment and performing manual labor as project
needs require.
● Perform daily equipment inspections and basic maintenance; report issues promptly.
● Operate all equipment in compliance with company safety policies, job specifications, and site
conditions.
Crew Leadership & Jobsite Management
● Lead by working side-by-side with crew members to ensure tasks are completed correctly,
efficiently, and on schedule.
● Set the daily pace and expectations for the job site by organizing priorities and maintaining a
steady workflow.
● Hold crew members accountable to quality, safety, and productivity standards.
● Provide clear direction while fostering teamwork, morale, and mutual respect.
● Serve as a steady, solutions-focused presence on site who keeps the crew aligned and
productive.
Planning & Execution
● Read and follow project plans, layouts, and schedules accurately.
● Anticipate challenges and proactively adjust workflow to stay on time and within scope.
● Communicate progress, material needs, and concerns clearly with management.
● Maintain clean, organized, and professional job sites from start to finish.
Company & Client Representation
● Uphold Chiles Enterprises’ standards of professionalism at all times.
● Communicate respectfully with clients, vendors, and other contractors as needed.
● Serve as a role model for safety, work ethic, accountability, and attention to detail.
Requirements
● Previous experience as an Equipment Operator, including familiarity with skid steers,
mini-excavators, and related machinery.
● Demonstrated willingness and ability to perform physical labor in addition to operating
equipment.
● Strong understanding of safety regulations and a commitment to complying with all safety
directives.
● Excellent organizational and time management skills with a strong attention to detail.
● Physical strength and stamina to safely perform manual labor and equipment operation
throughout the workday.
● Clear and effective communication skills.
● Willingness to learn and use the Aspire software system.
● Flexibility to work extended hours when needed. On rare occasions, availability may be required
for snow removal or emergency response.
● Valid driver’s license with an acceptable driving record and strong personal safety history.
This is a working leadership position. Candidates must be comfortable performing physical labor daily
while also operating equipment and leading a crew.
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.
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.com