Job Application

Please have the following general requirements to continue with the selection process.

Proficient Bike Mechanics

We expect our Guide Candidates to be competent and confident in the following Intermediate Bike Mechanic Skills BEFORE arriving at Guide Training:

  • Remove and replace either a tube and/or tire from both the front and rear of a bike, and properly seat the wheel in the dropouts with proper tightening of the quick release lever in 5 minutes or less
  • Remove and install pedals in 5 minutes or less
  • Adjust a bike saddle, both height and fore/aft position
  • Properly adjust both brake pad alignment and lever throw on a road bike
  • Adjust a bike helmet for the proper fit
  • Demonstrate general familiarity with carbon fiber bike frames
  • Change a handlebar stem and properly tighten to the specified torque

Strong Physical Fitness

Guides mainly split their time between bike and van support however must be physically fit to ride every day if needed. must be comfortable riding the distances and terrain on all road bike trips.

In addition to cycling, we expect all Guides to comfortably lift 50lbs over their head. Guides are required to load and unload 20+ bikes on top of our vans, porter guest luggage and move large coolers and bins.

COVID Vaccinations

We require all guides to be fully vaccinated against Covid-19, and to provide proof of such prior to any in person meeting with CT staff.  Further, guides are required to obtain booster, when the CDC recommends them for individuals in the travel industry.

Proficient Driving

Proficient driving 15 passenger vans while pulling a trailer.

Clear Driving Record

We will ask for a driving record at the candidate’s expense prior to the Training.  Candidate agrees that company may perform driver history checks on the candidate as a condition of their contract. Note, your driving record must have no more than 3 moving violations in the last 3 years. We will not hire anyone with a DWI/DUI (driving while under the influence of alcohol) conviction on his or her record, regardless of when the offense occurred.

Age Requirement

In order to comply with our liability insurance, all potential Guides must be at least 23 years of age. There is no age limit.

Travel Experience

Having spent time travelling and experiencing other cultures certainly increases your odds. We look for candidates with an expansive worldview who relish the idea of working in other regions while imparting their knowledge of those experiences and cultures on Guests.

Strong Computer Skills

  • Familiarity with Drop Box
  • Comfortable with both Internet and Email
  • Comfortable using a smart phone and capturing quality photos
  • Familiar with GPS tracking devices and creating routes online
  • Able to upload and download .gpx and .tcx files

If hired, Guides will need to provide the following items:

1. Current First Aid and CPR Certification

All candidates offered a Guide Contract will be required to obtain their First Aid Level 1 (or Basic) as well as Adult CPR certification, valid until the end of the year, and submit a copy of these to the Carolina Tailwinds prior to commencing work. Guides are responsible for the cost of this certification and responsible for submitting evidence of re-certification yearly.

2. Scanned copy of your valid driver’s license

Guides must also be in possession of a valid drivers license and it is the responsibility of the Guide to obtain the drivers license. We will ask for these items prior to attending the Guide Training Event.

3. Bike tools

While all of our units come fully stocked with extensive bike repair tools, Guides are expected to have a basic tool kit with them at all times while riding bike support. This includes a multi-tool (1.5-8mm), torque wrench, set of tire levers, and a small patch kit and a portable pump.

4. Camera-equipped, web-enabled smartphone

All Guides are required to provide their own web-enabled, camera-equipped smartphone. Your daily pay rate includes a per diem for phone use, therefore all costs associated with the use of your cell phone while guiding are the responsibility of the Guide, so it is advised that you keep all cell phone receipts for tax purposes.

5. Guide clothing

Carolina Tailwinds provides 1 cycling Jersey and 2 work shirts at no cost to every Guide given a contract.

Ready to Apply? There are a couple of ways to get started:

No phone calls, please.

Option 1:

Email the following information to

  1. Cover Letter: Explain to us why you feel you are the perfect candidate for this job.
  2. Resume: Please send us a 1-page, updated resume. Show us what makes you unique.
  3. Two Letters of Reference (optional): Provide two reference contacts OR two letters of reference from former employers or other professionals who can vouch for your suitability for this job.

Option 2:

Download our employment application and submit it via the website. You may do that here.

No phone calls, please.