Hire me, Cloudbeds!

Welcome, hiring manager for Cloudbeds!

You are here because I have applied for the currently open Compensation Analyst position. I appreciate you taking the time to consider me for this role. I’m confident you’ll be glad you did.

Please allow me to introduce myself…

Why I want to work at Cloudbeds

The Cloudbeds values inspire me and depict a setting in which I could thrive. What company history and financials I can find indicate the company is on an upwards trajectory. I want to spend the next chapter of my career applying all of my experience and skills towards the growth of a modern, valued brand.

Cloudbeds fits that vision perfectly.

I’ve spent hours researching Cloudbeds, the company, and what I discovered increased my enthusiasm for pursuing this role. I read about:

The good

Employee reviews on sites like Glassdoor and Indeed were encouraging. Ratings for the company are generally quite high and the comments paint an attractive picture. Even those critiquing the employee experience wrote things like “Hard work will be recognized and the culture is outstanding” which is of the utmost importance to me. I do work very hard and I do care a lot about culture.

I am very ambitious and driven so room for career growth is also critical. Fortunately, many reviewers expressed that room for growth is a strength at Cloudbeds.

The bad

Numerous reviewers wrote about compensation negatively. I read comments like “Pay isn’t on par with similar roles in the industry” and “Pay is terrible”. For many candidates this would likely be a cause for concern and hesitation but for me, due to the nature of this particular role, it is exciting. It means we have a lot of very important work to do.

I want to be a part of improving compensation at Cloudbeds and changing any negative perceptions about how the company pays employees.

In my experience managing compensation at software companies, I have learned that employee satisfaction is not just about the amounts. It has so much to do with how the compensation system works and how transparent the system is. While at Sandhills Development, I developed a custom compensation system which, after implementation dramatically changed employee attitudes. Prior to that project, most employees were dissatisfied or at best, confused when it came to their pay. After, I surveyed the company and over 90% of employees stated they were “satisfied” with their pay. The rest said they were “unsure” and zero employees said they were “not satisfied”.

Why I’m a perfect candidate to analyze compensation at Cloudbeds

I’ve handled all aspects of HR and People Operations

For the last five years I’ve been working in People Operations at growing software companies. In those roles, I was responsible for researching compensation, designing our compensation system, communicating system mechanics to all staff, and ensuring all employees were paid appropriately and fairly. It was also my job to design a framework for career growth within the company which featured job levels, detailed evaluation criteria, and transparent incentives.

But I don’t just bring the necessary skills and experience. I also bring passion. Compensation is immensely rewarding to work on and the work never ends. This is what I want to spend every day doing.

I satisfy every requirement for the job

Requirements taken directly from the job posting:


  • Bachelor’s Degree or equivalent is preferred

    • I graduated from Siena Heights University in 2012 with a Bachelors in Business Administration.
  • Must have a minimum of 5 years of progressive Compensation experience

    • In addition to managing compensation as the owner of a small business for five years, I was solely responsible for compensation at my previous employer Sandhills Development.
  • Experience in a high-tech organization is highly desired

    • My three most recent employers were software companies.
  • Incentive design and/or design involvement experience preferred

    • I was responsible for designing and implementing all incentives at Sandhills Development.
  • Advanced skill level in Excel, including use of V-Lookups, pivot tables, and pivot charts is required

    • ✅ In addition to designing and using advanced spreadsheets on a daily basis for my work, I used to teach Excel classes at a local college.
  • Proven project lead experience is required, including needs identification and assessment, gap and modeling analysis, and solution design and implementation

    • I’ve been managing projects of all sizes for the past twelve years.
  • Experience with Workday is highly preferred

    • ⚠️ I haven’t yet had the opportunity to use Workday but I’ve used similar platforms such as BambooHR and HR360.
  • Ability to work and build relationships remotely

    • I’ve been working remotely for over ten years and love it.

What others have to say about working with me

Don’t just take my word for it. Here are former colleagues voluntarily endorsing me:

Steve Bennett, Co-founder, Real Big Marketing (former business partner)

“…You can’t ask for a more well rounded individual.”


Pippin Williamson, Founder and Managing Director, Sandhills Development (former boss)

“Kyle is one of the most dedicated, hard-working, and caring people I have ever had the opportunity to work with”



Tyler Lau, Partnerships Manager, Sandhills Development (former direct report)

“…we were very lucky to have {Kyle} on our team.”

Adam Silver, founder, ConciergeWP (former client and podcast co-host)


Kyle constantly amazed me with his industry insight and original approaches to solving problems. He consistently demonstrated a strong work ethic and has a dedication to success.

Kyle brings intelligence, creativity and leadership to any project he is involved in. On account of his mature approach to his responsibilities, I often thought of Kyle as a colleague I could always rely upon to get the job done. I have always felt he was one of the best in class and it was a pleasure working with him.

Mandy Jones, Content Manager, Sandhills Development and Paid Memberships Pro (former colleague)

2020-02-11 10.18.55

Without a doubt, Kyle is one of the most valuable, hardworking, genuine, and thoughtful people I have ever met. After working with him for over two years at two different companies – Sandhills Development and Paid Memberships Pro – I know his character very well, and feel particularly well-suited to vouch for him as a friend and colleague.

Since I’ve known Kyle, he has brought tremendous value to the teams we’ve been a part of together. He not only pioneered a game-changing career progression framework and made massive efforts in planning and organizing events as Director of Operations at Sandhills Development; He also spent countless hours getting to know his colleagues (including myself) on a personal level.

It’s always been obvious that Kyle is totally invested in helping everyone on his team reach their highest levels of performance and personal satisfaction. Plus, his ability to see different perspectives and potential outcomes make him an excellent communicator and strategist across multiple arenas.

However, even with his creative talent, mind for business, and technological savvy, what strikes me most about Kyle is his kind, earnest nature. He is truly the kind of person you want on your team – the full package.

You can read more positive comments about me in the Recommendations section on my LinkedIn profile.