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


Tidewater Roofing is one of the region’s most trusted roofing contractors, providing services for more than 30 years to both residential and commercial clients. The company was established in 1982 and understands the value of quality products. That’s why in 1999, we established Carefree Gutter Guard which installs America’s BEST leaf-free system. Both companies remain family owned and operated.Our company proudly maintains full-service operations throughout Hampton Roads. We are a registered Class-A Contractor, are state and locally licensed, and are fully insured. We are currently hiring for a full-time Assistant Project Manager with experience in the Construction/Roofing/Gutter business. You will work directly with the Production Manager, assisting him/her and learning the role, with a strong focus on Customer Service.

Job Responsibilities include:

  • Schedule and manage jobs.
  • Communicate with homeowners before, during and after the job.
  • Make sure the materials on site match the Material Order and are kept in inventory.
  • Provide Production Manager and Crew with information to assist in production issues.
  • Produce and Distribute weekly reports for Production Manager and crew.
  • Scan and Upload all finished Work Orders to job in CRM.
  • Previous experience in the Roofing/Restoration industry (preferred)
  • Detail-oriented, great at spotting imperfections/subpar work
  • Great communication skills
  • Must have or build a reliable subcontractor network (roofing, siding, windows, painting, gutters, etc)
  • Good at balancing cost vs. quality of work

Why should you apply?

  • Pay commensurate with experience
  • Great work environment
  • Serious and stable company committed with customers and quality
  • Paid Time Off
  • Vacation Time
  • Life Insurance

Job Type: Full-time

Pay: $10.00 – $15.00 per hour


  • Employee discount
  • Life insurance
  • Paid time off


  • 8 hour shift


  • High school or equivalent (Preferred)


  • Production management: 1 year (Preferred)
  • Production planning: 1 year (Preferred)

Work Location:

  • One location

Typical start time:

  • 7AM

Typical end time:

  • 5PM

This Job Is Ideal for Someone Who Is:

  • Dependable — more reliable than spontaneous
  • Detail-oriented — would rather focus on the details of work than the bigger picture
  • High stress tolerance — thrives in a high-pressure environment

This Company Describes Its Culture as:

  • Detail-oriented — quality and precision-focused
  • Aggressive — competitive and growth-oriented
  • Outcome-oriented — results-focused with strong performance culture

This Job Is:

  • A job for which military experienced candidates are encouraged to apply
  • A “Fair Chance” job (you or the employer follow Fair Chance hiring practices when performing background checks)
  • A good job for someone just entering the workforce or returning to the workforce with limited experience and education

Company’s website:


Company’s Facebook page:


Work Remotely:

  • No

You can also view this posting here.

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


Richmond VA