Position: Full Time
Location: Remote

Kenny Flowers is looking for an experienced Executive Caddy (Assistant) to join our small, driven team. 

Think of yourself as a pro caddy to an ambitious golfer. You learn and know the lay of the land and will do whatever it takes to help Kenny succeed on and off the course (in and out of office). 

As a growing D2C business and leader in paradise, this role is critical to help Kenny Flowers continue to scale into a leading lifestyle brand around the world.  You will work directly with and for the Founder/CEO Kenny, managing his schedule, time, tasks, interests and logistics. You are ready to think 5 steps ahead of him. Keep him organized, prioritized and help him thrive so he can lead the charge helping others around the world from our customers to employees to supply chain. 

The successful candidate must possess exceptional organizational skills, excellent written and verbal communication skills and be flexible and ready to take on a variety of tasks to help Kenny & Kenny Flowers succeed. 

We want this to be the coolest job you’ve ever had, and the beginning of an awesome new future with Kenny Flowers!

We want this to be the coolest job you’ve ever had, and the beginning of an awesome new future with Kenny Flowers.

Key Responsibilities

  1. Organizing meetings, including scheduling and sending reminders.
  2. Manage Kenny’s calendar and ensure meetings are adjusted according to his ever changing time zones. :)
  3. Act as the point of contact among employees and other external partners.
  4. Keep all projects organized and prioritized for Kenny, with extra focus to time blocking his involvement.
  5. Filter emails and bring important items to Kenny’s attention.
  6. Provide administrative assistance, such as drafting emails, and preparing communications on Kenny’s behalf.
  7. Make travel and accommodation arrangements.
  8. Attend meetings to take notes and assign follow up tasks to Kenny (and the team).
  9. Your responsibilities will mostly be business related, but at times you may assist with Kenny’s personal scheduling, time, logistics, etc.


You are highly organized, self-motivated, responsible, a hard worker and a clear communicator.

  1. An exceptionally organized individual who thrives under pressure. 
  2. High School degree. Personal Assistant diploma or certification is a plus.
  3. A minimum of 2 years’ experience as an executive assistant.
  4. Confident using Gmail, Google Drive and docs, Word and Excel. 
  5. Discretion and confidentiality.
  6. Creating systems and workflows that will improve efficiency, organization and free up time for Kenny. 
  7. As a first point of contact, you must be a strong written and verbal communicator who can present themselves professionally on behalf of Kenny while also staying true to the Kenny Flowers brand. 
  8. Be available and flexible to meet the needs of our CEO who is often travelling the world and may be in a different timezone. 
  9. Willing and able to travel when needed throughout the year. 
  10. Able to take direction but operate with minimal supervision, thrive working independently in a constantly-evolving atmosphere. Preferably have prior experience working remote. 
  11. Desire to contribute to an awesome company and product. Hungry and motivated to get Kenny Flowers to the next level. Wholeheartedly embody the lifestyle that Kenny Flowers aims to bring out in others.
  12. Be adaptable and ready to grow. We are a small company which means this position has growth potential for the right candidate.

    Who you’ll work with:

    1. Work with and report directly to our CEO Kenny Haisfield. 
    2. Internal teams and employees, as well as external partners.

    Apply Now

    To apply please email jobs@kennyflowers.com with subject line: Executive "Caddy" Assistant - YOUR NAME.
    Please include your resume, your social media handles, and a cover letter.