2026 Winter Entry-level Jobs in Chesapeake, VA
Looking for Chesapeake entry-level jobs? Virginia’s third-biggest city is a key player in the massive center for East Coast commerce and culture known as Hampton Roads, and was named the 21st best city in America by Bloomberg Businessweek in 2011. Despite its economically powerful and visually stunning location, Chesapeake is known for its focus on protected farmlands, forests, and wetlands as opposed to sky-scraping urban centers. To highlight this emphasis on gorgeous East Coast nature, some points of interest in the city include the Chesapeake Arboretum, the Chesapeake and Albemarle Canal, and the misleadingly named Dismal Swamp Canal. But don’t let the lack of downtown high-rises fool you; Chesapeake entry-level jobs will offer you a wealth of experience and knowledge by putting you among the ranks of top-tier companies in several different fields. Some of the top employers in Chesapeake include QVC, HSBC Finance, Cox Communications, and Hewlett-Packard. For entry-level job seekers interested in the healthcare industry, there’s the Chesapeake Regional Medical Center, Sentara Healthcare, and LTD Hospitality Group to choose from. Interns looking to work in media, transportation, or government might also find Chesapeake to be ripe with worthwhile opportunities. Take a look at our list of Chesapeake entry-level jobs below and start taking your next steps towards invaluable work experience today.
Experienced Gutter Installer
Intern Engineer
Armorer (OBMLS Specialist II)
PART-TIME Registered Behavior Technician
Intelligence and Information Security - Officer Careers - VA, DC, MD
Full time physical therapist
Marine Electrician
Construction Superintendent
Experienced Bookkeeper
# 2646 Associate Systems Engineer (SE20) -Virginia Beach, VA
Freight Dispatcher (Independent Contractor) — $1,800 to $4,500+ Weekly Potential
Freight Dispatcher (Independent Contractor) — $1,800 to $4,500+ Weekly Potential
Entry-Level Freight Dispatcher – Weekly Pay: $1,800 to $3,200+
Entry-Level Freight Dispatcher – Weekly Pay: $1,800 to $3,200+
Entry-Level Freight Dispatcher – Weekly Pay: $1,800 to $3,200+
Neurology NP (or PA)
Commercial Disaster Restoration Sales Representative
Clinical Assessor
Administrative Assistant
Property & Casualty Small Business Insurance Advisors
Licensed Practical Nurse at Residential Group Home
Financial Representative - Entry Level
Apprentice Gutter Installer
Caregiver
Caregiver
Real Estate Listing Agent
$180,000 per year
Human Service Professional - Suffolk VA
Architect / Senior Project Manager – Retail / Commercial Studio
Diesel Mechanic
Physician Assistant - Officer Careers - VA, DC, MD
Direct Support Professional
Mental Health Therapist
Specialty Account Manager
Licensed Practical Nurse/ RNs and PRNs - RCSU Facility
Mental Health Therapist
Garage Door Installer
Life Coach- Portsmouth, Suffolk and Franklin areas
Area Manager 2026 – KY, VA (Recent and Upcoming Graduates)
The base pay for this position ranges from $63,600/year in our lowest geographic market up to $82,700/year in our highest geographic market.
Away Travel Merchandising Rep
Direct Support Professional (DSP) – Day Support Program
Direct Support Professional (DSP) – Day Support Program
Real Estate Sales Buyer's Agent
$135,000 per year
Executive Chef
VEWWS Mobile Heavy Equipment & Diesel Mechanic
Field Inspector I
Licensed Massage Therapist-SIGN ON BONUS
KHI Medical Traveling Installation Technician
Advanced Practice Provider-Full Time
Custodian I, II, III
Traveling Surveyor (Independence Excavating)
Class A CDL Driver - New Equipment
Business Analyst
Experienced Restoration Technician
Looking for Field Sales Agent (ACP PROGRAM)
Dedicated | Semi-Local | CDL-A Truck Driver
Registered Medication Technician
Brand Rep - Audits, Merchandising and Quality Control
Real Estate Sales Buyer's Agent
$104,000-$206,000 per year
Travel Healthcare Inventory Auditor
Housekeeping Supervisor
Engineer - Officer Careers (VA, DC, MD)
Housekeeping Supervisor
Restoration Reconstruction Project manager
Real Estate Sales Listing Agent
$140,000 per year


















