Undercover Boss Analysis of Stephen J. Cloobeck: CEO of Diamond Resorts International


“Undercover Boss” is a new television series that takes real top-level executives of large corporations, and plants them in entry-level positions in their own companies, disguised as just another John Doe, to see what really goes on in both the front-lines, and the minds of their employees. The Collared Sheep will be providing analysis of each executive in each episode, because, well, we all work for CEO’s like these.

Stephen-J-Cloobeck-CEO-of-Diamond-Resorts-InternationalName: Stephen J. Cloobeck
Title: CEO of Diamond Resorts International
Headquarters: Las Vegas, NV
Product or Service: Hospitality and Vacation Resort Brand

Brief Overview:

In this week’s episode of “Undercover Boss”,  Stephen J. Cloobeck, CEO of Diamond Resorts International, goes undercover to gain perspective into the lives and jobs of the employees at his company.



Quite the disguise.

Position 1: Resort Engineer

Overview: Stephen Cloobeck goes under cover as “Jack Fisher”, assist Randy at his first trial position of resort engineer. He stands by with a fire extinguisher as Randy welds a broken AC unti on the building rooftop. He later helps Randy replace old lights with new standard Diamond Resorts lights.

Result: A small fire breaks out, but the pair is able to contain it. Cloobeck overcomes his fear of the ladder (not the corporate one, that’s for sure). Cloobeck learns that Randy once owned an RV repair business, but the company that purchased it owed Randy 240k before declaring bankruptcy. Randy and his wife are now forced to work two jobs to prepare for retirement.

How he made amends: Cloobeck awards Randy $150k to pay off his entire mortgage, and throws in an additional $50k in cash as icing on the cake.

What he should have done: Cloobeck really didn’t change anything about this role in particular, but in this short segment, you would be hard pressed to find even one real job related issue. Our first thought was lack of safety while welding the roof unit, but they did have a fire extinguiser and wet cloths (I’m not AC technician, but that sounds reasonable).

Cloobeck earned some major generosity points by paying off Randy’s mortgage. He also had his own share of business deals gone bad, so this act really brought his empathy to the spotlight.


"Damn, I knew we should have used Priceline."

Position 2: Booking Agent

Overview: Stephen listens in as Sarah answers calls from customers looking to make reservations at various locations.

Result: Sarah makes a number of painfully apparent errors – such as not spelling a destination location correctly in the system, preventing her from providing potential reservation dates. After about 4 in a row, Cloobeck explodes, reveals his identity, and marches directly to Sarah’s supervisor. He is displeased with their training, to say the least.

Doing his short stint as a booking agent, he learns that Sarah is working towards a business degree in college, while working for Diamond Resorts.

How he made amends: Cloobeck first apologizes, stating that it is not Sarah’s fault for her lack of proper training. He states that he will now be personally training each team member at the facility. Cloobeck awards Sarah and friend a first class trip to Hawaii (hoping she will learn the Hawaiian resort names, half jokingly), and pays her $15k, to cover her school loans.

What he should have done: Was it actually the entire team booking agents who required training, or just Sarah? That’s the real question. Either way, a CEO of a company this size has got to have better things to do than spend time retraining the entire squad of booking agents.

Cloobeck should have pressured their direct managers to improve their performance and training, and setting some new standards. It’s their job to train the agents – not the CEO’s.


Raisin' the roof. Well, sanding it at least.

Position 3: Painter

Overview: Stephen follows Greg from building to building, performing various touch-ups, such as  sanding down walls to be repainted, and calling in leaks to the technical team.

Result: The job itself is relatively unpleasant – Greg is forced to use a hand sander on the ceiling, rather than a power sander, which adds considerable time to the job. The safety glasses and masks they use are on the lowest-of-the-low-end of things, and make it difficult to see/breath.

Greg notes several difficulties with the job, specifically the fact that there are hundreds of buildings for each employee to monitor, spreading them very thin. He also notes his displeasure with the fact that he had been there for several years with no pay increases. Cloobeck learns that Greg enjoys cooking on the side, and because he has car trouble, has trouble making it to work.

How he made amends: Cloobeck states that he will be upgrading the safety googles and masks, as well as providing electric power sanders, to assist Greg and the other Painters. He says he will work to  improve the staffing issues. He enrolls Greg in a “meat of the month club” (it’s like Clark Griswold’s “jelly of the month club, but with meat”), and buys him an industrial freezer. Additionally, Greg is given a new hybrid truck, and a $20k cash bonus. Cha-ching!

What he should have done: New power tools for better efficiency? Check. New goggles and masks for better safety? Check. New employees for better staffing? Check.

Cloobeck aced this round, and his added generosity did not go unnoticed.


"...And this is where the overbooked reservations go!"

Position 4: Front Desk

Overview: Amanda shows Stephen how to work the front desk at one of the resort locations, checking people in and out.

Result: Stephen is shocked to see that the front desk was still using  an archaic hand written paper system for scheduling and bookkeeping. Amanda describes her displeasure in how they are told to deal with overbooking – they are essentially told to inform the customer that an unfortunate maintenance issue is preventing them from assigning the room. Apparently, several customers didn’t take this so well.

Cloobeck learns that Amanda’s mom has multiple sclerosis, and Amanda is struggling to chip in with her medical bills. Amanda states that she would go to Ireland, if she could go anywhere.

How he made amends: Cloobeck says he will be changing script used to deal with overbooking situations, specifically by proactively contacting customers much earlier to let them know of overbookings and provide new arrangements. Amanda is offered a position to work in Ireland, and is awarded a $50k cash bonus.

What he should have done: Stephen Cloobeck nails the overbooking problem, but fails at the easy layup – the paper based bookkeeping system. He even says himself “C’mon, its 2010!”

Cloobeck, get back in there and upgrade this site to a modern day scheduling and reservation system. Ditch the paper, save some trees, and make it easier on your employees at the same time.



For the most part, YES.

Stephen Cloobeck earned a “B” grade for his appearance on Undercover Boss.

Admittedly, it was within inches of an “A”, considering his generosity – but you can’t buy your way through this test. He missed the necessary IT upgrades for the front desk team, and took a rather unorthodox approach to the training issues of his booking agents.

Finally, the one side note that cemented him in “B” territory was the fact that he opted not to stay in a low grade hotel while away from home, and instead stayed in a fancy 5 star hotel. A minor detail, but still – to get the truest sense of what it might be like not to be CEO, he should have lowered his standards a bit just for that week or so.

Don’t like our grade? Drop us a rebuttal, and leave a comment below.


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49 Responses to “Undercover Boss Analysis of Stephen J. Cloobeck: CEO of Diamond Resorts International”
  1. Randal Wong says:

    Since its debut on CBS, I have watched a majority of episodes of Undercover Boss. I was amused by Mr. Cloobeck’s arrogance and conceit. He was cavalier regarding his wealth and position, taking pride in himself rather than in his deserving employees. His overblown assessment of his abilities, as well as his properties, was ‘uncovered’ as he demonstrated his incognizance of the day-to-day operations of DRI properties.

  2. Jbone says:

    Anyone else think his wife married for love? womp womp

  3. Jimmy says:

    Cloobeck was truly an arrogant narcissistic dick. This show was really him taking the opportunity to flaunt his wealth and make sure he was scene. I think he just wanted also to advertise his product.

    He has purchased his wife, not sure if he’s humble enough to actually know that though.

  4. Corey says:

    Wow, this guy is a the king of all doosh bags. How about that violation of HR policy by calling that call center rep “babe”?
    Wow, this guy is a total tool.

  5. McFly says:

    A tool? Perhaps, but he sure was a generous one.

  6. Shirley says:

    I was so looking forward to the new episode however I turned it off after the first 5 minutes or so. This CEO was way to stuck on himself and his wealth.

  7. Fred says:

    Agreed – a complete douche bag.
    He was looking for people to kiss his a$$ and stroke his ego.


  8. Don P. says:

    Funny thing is his “WEALTH is as FAKE as his TAN” His empire is made up of a bunch of unhappy members just google it if you don’t believe me.

    Don P.

  9. Shawn S says:

    What a total douche bag, my favorite part was the very last scene of him in the hot tub or whatever with a glass of champagne, so humbe. I’m actually glad I saw that episode now I will never stay at one of his resorts.

  10. Kat says:

    I’m a unfortunate owner of points in Diamond resorts, so the doosh bag was throwing his money about, well owners money really! As one of his first great moves on taking over the company was to practically double the maintenance fees.

    I’m in the UK so we cannot see the us ‘Undercover boss’ but he looks to be a bit odd ( plastic surgery on the eyes ect??)
    Can someone put this episode on u-tube please, so we in the UK can see it!!

  11. Jen says:

    This man is not a nice man. The fact that the sales agent even got a second chance is surprising because on a daily basis, this company fires sales agents for reasons such as a client getting disconnected from a phone call. They hire masses of agents and train them – it takes about 3 months, and entire classes are already gone – FIRED. good thing they hire in between though to have agents to replace those that were fired for any perceived transgression. This company is not loyal to their staff and this man and his rules are heartless.

  12. Jason says:

    Total douche… How does he think he is soo important that he needs a personal sercurity commando doing sweeps of hotel rooms for him. He says there are alot of ‘crazies’. For him? Does he think he is some sort of celebrity? I bet no one would even recognize this guy AFTER this show premiered.

  13. […] hospitable side of yourself. People will follow your lead into some amazing places. Interestingly, an analysis of this CEO rated him with a “B” grade. I think what the analysis failed to take into […]

  14. carlena says:

    I thought he was a man who cares deeply for his employees and really made a difference in their work loads and personal life. He lives a high life, of course, he worked hard to get there. Dont attack him personally,,,if so,,its because your jealous. I would love to work for this man.

  15. Pammy Jean says:

    I just watched uncover boss, never saw this program before,I was in tears for what Stephen did for all his people, what a wonderful, kind, caring, giving man he is. He literally changed the lives of these people, not to mention improving his business, which will benefit so many other people. I am 67 years old and this man brought tears to my eyes with each gift he gave, you could feel his heart. God bless him, we need more like him, what a better world this would be. He is so successful, and will continue to be, he’s smart, but not self absorbed, it’s not always about money, his heart is huge. May God keep blessing him. Thank you.

  16. John Russo says:

    Mr Cloobeck,I just watched this Undercover Boss show for the first time and was so impressed the way you run the business.A true man of integrity,and what you did for your employees touched my heart, so special. My name is John Russo and I’m about to leave the entertainment business,where I wear many hats,specializing in keeping celebrities content and safe.I am a very personable man.I have just purchased a home in Scottsdale and I may be looking for some work,it would be my honor to be part of your team,I would like to send you a some references and tell you a little about myself or your GM in Scottsdale.I hope email gets to you,if not Bless You for what you did for your staff.
    Thank you,
    John Russo

  17. judalon smyth says:

    I would give him and F because I just had the worst resort experience of my life at his Sedona Summit Resort and all 20 of our party (11 rooms) had major issues and problems. As the host for our group I was the one working with his staff to resolve problems and as a result my civil rights were violate, I was treated rudely, my character was maligned, I was threatened and have bruises on my arm. At 4am there was a peeping tom on my patio who ran off when I turned my light on after hearing him bang the chair against my sliding glass door and I couldn’t call the front desk because they were all hostile and part of me believed it was them trying to frighten me. All this ill treatment began because my group is a travel club and we travel all over the world at many different resorts & I always greet our members in the lobby of where we stay to give them our gifts and itinerary. This was all pre-booked and arranged with Diamond Resorts, but one of their employees who lied and told me she was the owner of the excursion company/services, yet I later was told that Stephen Cloobeck owns the excursion services. This company calls themselves a “vacation Club” which is a misleading term for TIME SHARE PRESSURE SALES. The employee claiming to be a business owner accosted me and I asked her to leave me alone she decided I was competition to her “business” and she went and told some crazy story to the general manager who rather than act in the interest of me the paying guest he became all about her and making me wrong telling me I couldn’t be in the lobby which was the only place my cell had even poor reception. I was told I could not wear my shirt with our club name on it. I was told I could not leave notes for my club members if my note paper had my club name on it. It goes on and gets even worse. I felt physically unsafe. I had members of my party who had to move their room three times because of chemical and mildew smells, broken ac or noise. The show didn’t reveal the worst of the problems at this business which is not about the customer but all about the ego of the employees who thing paying customers are here to serve them. Their cleaning crew doesn’t even have to take out the trash in your room they have a sheet of paper they give you after check in that tells you that you must take you room trash to a trash site but its not easy to find. It’s just not customer friendly… they are nice only until they can determine if you are going to buy one of their time shares which they claim is a vacation club. Mr Cloobeck is not a very good boss based on how ego and full of themselves his employees are. He may be able to buy off his employees but he sure doesn’t care about giving his customer any value for their money spent. When I told his staff how unhappy I was and that I was going to give them a bad review I was asked to check out of the property and was given 90 minutes to check out of a room that had been pre-paid so when I checked out their front desk people took 45min to figure out how to handle the fact that they owed me money & I didn’t get that money in my hand when I left I was told I’d have to apply for it. Why didn’t your show uncover the real Diamond Resorts. I can’t believe the award I saw on the front desk counter “Best Resort 2011” it’s a dump and service is the worst in the world.

  18. McFly says:

    Judalon – that was quite a venting

  19. Michael says:

    Dude was a straight up ass. I’ve rarely thought it was silly when people boycott a company or something but this was an instance that I said to myself that I won’t stay at one of his resorts and put more money in his pocket. He was a douche and I hope all his employees are able to find good work at competing resorts.

  20. Someone should try doing a show on his whore-mongering, infidelity & cocaine use…

  21. robmar says:

    They should do follow-ups at the companies they profile and see how the rest of the employees feel when they find out that 3 or 4 of their fellow employees have been given great gifts when perhaps they themselves and obviously other employees are hurting just as much or even worse than those lucky enough to have been on the show. It may make great TV but I have a feeling that it does more harm than good to morale of the companies actually profiled.

  22. the shiny seaturtle says:

    Cloobeck & his brother are the worst kind of cocaine snorting prostitute banging douchelords out there. I hope his wife Chantal doesn’t find out, LOL….

  23. Southwest Woman says:

    Seriously? This guy is generous? No. He mistakenly is trying to look generous by giving excessive money to people he barely knows in order that people will say, “Wow! What a great guy!”. He is a total narcasist. (pardon my spelling). My husband and I got hooked into this episode because we were fascinated by what level of douchbagery he could reach.

  24. Rae says:

    The level of arrogance this man displays is comical. A security detail? Seriously? Clearly this was an ego adventure for him. It did give me an interesting view of several ‘diamond’ resorts and the quality of the units and resorts is clearly low end. I am glad my timeshare is with another company. I would never stay at a Diamond resort and certainly won’t do it to support a CEO who is so offensive.

  25. Briana says:

    First 15 minutes and I’m not impressed… just annoyed. I’ve seen some good Undercover Boss episodes where you know the CEO’s have serious dough but don’t flaunt it whatsoever. First thing was talking about HIS jet, What his wife is famous for, his personal security guard, and of course that ridiculous hotel upgrade! He really made the impression that he is full of himself. I’m sure he’s a nice guy, but if you want a real learning experience then start from the bottom up.

  26. Tammy Sykes says:

    I loved Mr. Cloobeck on Undercover Boss….He shows that he is a man of integrity, always thinking about his Brand and Customers. If given a chance I would love to work for that man…..God Bless you Mr. Cloobeck and God’s continued success….

  27. Doug Bartake says:

    If you look for the worst in people you will see it. If you look for the best in people you will also see it. It depends on how you CHOSE to look at people and the world. Many on here call Mr. Cloobeck names like douchbag and narcissistic and others call him a man of integrity and an honourable person. This is evidence and proves my point.
    I was touched by the look in people’s eyes and their response to Mr. Cloobeck’s generosity. From what I have seen and from watching the episodes on TV the intention is all that really matters. He wants to improve people’s lives and situation and for that Mr. Cloobeck gets a huge thumbs up in my book. I would love to work for a guy like this. He cares about quality, service, and PEOPLE. That’s a great combination! He can call me for work anytime!

  28. Mary Combs says:

    Thisis the second of Mr. Cloobeck’s undercover boss appearances. As a timeshare owner and a business owner, you DO NOT EVER chastise an employee in front of a guest or another employee

  29. marty says:

    Who is the blonde asian girl in the bungled hair drying spa scene. She looks like an actress I have seen before? Anyone have her name?

  30. Angel says:

    I don’t know if this is real, but I wish something like that happen on my company, specially to myself….

  31. Anthony(Gus)Simmonds says:

    Kia ora (hello)
    I’m from New Zealand.It is the 14.2.2013 1:52am.I am only awake because my step son is in hospital waiting on a hip operation.

    As much as I miss him and his lovely mother,I choose to wait patiently for there return home.Mr Cloobeck also chooses they way he is.I just finished watching under cover boss part two of diamond resorts.I have just made a wish of mine to one day meet this love,caring man.I think he is an amazing man with a huge heart.Some people might say he just flaunts his money,all I can say is “because he can”I bet if he gave the critics out there the amount of money he gave his workers,because he cares.I bet you wouldn’t dis him.I am a very proud Dad who raised my daughter up by myself for ten years of her nineteen years to date and now I’ve taken on a roll to become a awesome stepfather to a thirteen year old fantastic boy who’s father left him and his mother twelve years ago.It is my duty as a father to teach my kids trust,honesty,respect and most of all love.And that is all I saw in Mr Cloobeck.As they say people, good will always beat evil,and he is a good man.I’m not a wealthy man at all.But I’d rather try and fail wishing to meet him rather than fail not to try at all.I am an indigenous maori and all I can finally say is Tihei mauriora..which means(The breath of life)in my native tongue.

    To Mr Cloobeck you da man!!!!!

  32. You made me cry Stephen. That is how to help pple and you have become my role model. i watched the program from the start to finish am really really proud of what you did. Super, thumb up for you. i do mine too in my little way. Check elderlyandthepoor.org and tell me your likes and dislikes. God bless

  33. I’m a little frustrated that Ultimate Demon is definitely so capable. It makes all our hands-on working hard useless

  34. Dawn riggs says:

    People if you Google the man will see he gives to other charities and also help other people.Before show undercover boss.So stop saying being such haters because your jealous of the man
    Nobody perfect but the man is as close as you can get.You might not like his ways but the person he is on the inside that counts
    Money dont make the man look down on other or less fotune.
    And I am happy to know the man in a happy marriage with a pretty woman.We shouldnt judge her

  35. Dawn Zahrte says:


  36. Rick Felty says:

    We made a mistake in our fee for maintenance and tax’s. On Dec 31 2013. However it has taken until March 19. When I called Diamond Resorts ( AKA Mystic Dunes)to actually find out about it While inquiring about a pending request with IntervalI International. Finance and invoice recording in mystic Dunes Never sent me a deficient notification like they claim they’d on March 1, 2014 .Our check was Received on 31 December 2013 and processed. It has taken 3 months for me to find out about this deficient on my own inquiry. This is totally unsatisfactory account and invoice recording with Mystic Dunes in Celebration Florida. Someone Needs to be paper trailed and retrained On proper accountability from the supervisor on down. I understand a final notice would have been sent out and also to a collection agency on April 1. This is totally unprofessional performance.
    A collection agency would have made my credit standing appear to be inadequate. It is not appreciated. Stephen Cloobeck needs to address this directly to correct this performance and behavior within his Organization.

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  40. Linda says:

    I just got done watching undercover boss with Diamond resorts, that CEO is truly an ass! It’s not about you or your money it’s about the people whom make money for you, you are rude, stupid and not a body builder, your stomach over rung your pants! It’s about the people NOT YOU MR CLOOBECK, NOT HAPPY WITH HIS SHOW!

  41. hm, genuinely? i didnt become aware that

  42. arash.hayati says:


  43. arash.hayati says:

    سلام من برنامه شما رییس نامحسوس روازشبکه من وتو تماشا کردم افتخارمیکنم که هنوزانسانیت دروجودبعضی مردم مثل شما ازبین نرفته هرچندکه این موضوع ممکنه دربین افرادیک خانواده هم احساس نشه من متاهل هستم شغلم ارایشگری قلیم میگم بخاطربیماری کم خونی دخترم چون شرایط درمان مناسب اینجا نیست دوست داشتم دریکی از هتلهای شما شغلم رو انجام بدم چون دیگه هرروز شاهدضعیف شدن دخترم نیستم باورکنیدحاضرم تمام مخارج اومدنم رواونجا باکارپس بدم .دوستدارشما درکنارخانواده شادوتندرست باشید

  44. arash.hayati92@yahoo.com says:

    معذرت میخام که نتونستم انگلیسی بنویسم به امیداینکه هیچ پدری درد وناراحتی فرزندش رو هرگز نبینه بدتراینه که ببینه وتوان دفع ناراحتی وغم روازفرزندش نداشته باشه وارزوی شادی ولبخند فرزندش براش غیرممکن باشه شنیدن غم ودردمردم واقعا سخت اماشما دل دریایی دارید. شرمنده ام که باحرفام شمارو ناراحت کردم افرادخانواده به اینکار وحرکت من میگن سادگی اما من حس دیگه ای دارم نسبت به شما.دوستدارشما

  45. nanoo says:

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  46. Wilson McKee says:

    All that money he gives to those employees is from association fees that keep rising for all the owners. And then showing him flying all over the place in his private jet. This money he is wasting should be going into improving and upkeep of the properties, not into inflating his ego. This guy just pisses me off with his arrogance.

  47. Tommy Dean says:

    Gigantic arrogant self absorbed asshat grade A1. End of discussion.

  48. jaime Sanchez says:

    I see a good boss and who has a good heart so God blesses his family

  49. jaime Sanchez says:

    I see a good boss and who has a good heart so God blesses his family
    I see a good boss and who has a good heart so god blesses his family


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