Carefree Gutter Guard
701 Industry Drive Hampton VA 23661 757-690-2641
Carefree Gutter Guard
4944 Millridge Parkway E Midlothian VA 23112 804-709-3760

We’re Looking for People Just Like You!

Are You Interested in Working for a Long-Standing Company That Cares About its Customers & Employees?

As one of Hampton Road’s most well known gutter companies, we’re always looking for experienced, talented, and hard-working installers. We offer a great working environment and competitive compensation (including vacation time, benefits, and more).

About Carefree Gutter Guard

We first opened our doors in 1999, and over the past nearly-20 years we have grown into one of the most well-known gutter companies in Hampton Roads and Greater Richmond.

We are a family owned and operated business- no “big business” problems here! We have stayed true to what we know making us a market leader: personal service, genuine relationships, and a focus on quality and results that only a family-run business can have.

Learn more about us.

Current Openings:

Good with tools? Not afraid of heights? Are you highly motivated and looking for a place to begin a career? Want to work for one of the most successful, and fastest growing leaf-free gutter companies in the area? WE ARE LOOKING FOR SOMEONE LIKE YOU!

We searching for qualified candidates who are:

  • Willing, and ready, to learn from highly skilled and trained professionals
  • Highly motivated, skilled craftsman
  • Aspiring to become part of our team, long-term
  • Looking for growth opportunities
  • Great communicators, with superb customer service
  • Are always on time and willing to go above and beyond to assist their team
  • Reliable transportation, and a valid’s driver’s license (REQUIRED)


  • Balance: Installers work on roofs, which might have very steep pitches. Balance is crucial to the job and your safety.
  • Strength: Installers need to be able to carry heavy materials up ladders and onto roofs.
  • Stamina: Installers spend most of their day on their feet outside, sometimes during intense heat or cold.
  • No Fear of Heights: Roofs can be very high. Installers need to be steady and unafraid of being in high places.
  • Working knowledge of the industry’s procedures and safety.
  • Excellent communication, analytical, leadership, interpersonal, problem solving and organizational skills.
  • Experience with: sheet metal and woodworking
  • Must have access to basic tools such as a drill and hammer.
  • A valid state driver’s license (in good standing).
  • Able to lift 50 lbs. and climb up and down ladders to minimum heights of 25 feet.
  • Able to work within a TEAM environment.
  • Able to work Saturday and/or Sunday, if needed.
  • Authorized to work in the United States
  • May be asked to complete Drug Test and/or Background Test (Dependent on Specific Jobs)
  • Must have reliable transportation


This is a great opportunity to work with an established, vibrant company looking for a dynamic individual to represent us on the Southside of Hampton Roads. We are looking for a sales associate with a “hunter mentality”, meaning you are actively pursuing sales opportunities outside the leads you are given (i.e. taking time to visit clients and continuing to strengthen those relationships). THIS IS A FULL-TIME POSITION.


  • Valid ID and clean driving record
  • 2-5 years sales experience with proven track record
  • Outstanding customer service/ communication skills
  • Ability to climb ladders and walk roofs
  • Must be punctual, well groomed, well dressed, and must have better than average presentation and communication skills
  • Some heavy lifting may be required

Desired Skills/Experience:

  • Experienced in Residential Gutters.
  • Computer skills – Excel, Word and Outlook.
  • The ability to learn new programs and systems
  • Basic math, including geometry
  • Ability to write detailed proposals
  • Able to work in a Company environment
  • Team player
  • Organized

What to expect from us:

  • Paid Training plus Commission (Earning potential 75K to 100K)
  • Lead provided.
  • Company Vehicle.
  • Ongoing training


About the Company

Known & Trusted Since 1999.

We are proud of our legacy! With years behind us, we are thankful for all of our wonderful friends and customers that have helped us be a success. Just as we have in the past, we hope to continue to provide great service and an unmatched gutter experience for the next decades!

Job Type: Full-time

How to Apply:

  • In person at our office – 701 Industry Drive, Hampton, VA. 23661
  • Online with the form below

Hampton Roads


Greater Richmond