CADDIEMASTER Cares
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June 10, 2026 - A Letter from Dan
Hello Everyone,
I wanted to touch on some recent issues which we have heard from employees. One topic that has come up recently is job security. Some have suggested that caddies should be concerned about their future here at Pebble Beach without union representation.
I want to make clear to everyone that no one will be treated differently, disciplined or discharged because of how they feel about the Union, Company or the process. No one will be subject to unlawful retaliation. Don’t let anyone say otherwise. As CEO, we will always follow the law. It’s important for all of you to vote freely and in your own voice on June 18th. Don’t let anyone pressure you or bully you into making a decision that’s not best for you and your family.
I believe our history tells a very different story.
For more than 20 years, CADDIEMASTER has operated at Pebble Beach during a period of consistent growth. Throughout that time, our focus has remained the same: building and maintaining the finest caddie program in golf. The success of that effort depends on experienced, knowledgeable, professional caddies who know the golf courses, understand the expectations of our guests, and deliver the level of service that has become synonymous with the Pebble Beach experience. Simply put, our business is stronger when our caddies gain experience and remain part of the team. Everything we have done since the February 2026 announcement through all the Phase Meetings and updated FAQs has been focused on hiring and retaining our current caddies. You are all critical to our success as a Company. We know that and respect the job you do.
I’ve also heard concerns surrounding our tiered pay structure and the belief that because senior caddies earn more, the company would be motivated to replace experienced caddies with newer, less expensive ones. That notion is also not only inconsistent with our values, it would be counterproductive to our business. The experience, professionalism, and course knowledge that comes with tenure cannot be replaced.
We do not view experienced caddies as a cost to be managed; we view them as one of our greatest assets. The reputation of this program has been built by the dedication and expertise of veteran caddies, and our goal has always been to retain and develop that talent, not replace it. When we recruit new caddies, it is only to keep up with growth of the business and also make sure our current caddies have work/life balance. As we all know, there are some loops that senior caddies do not want to take – those loops need to be covered.
The strength of our program depends on having seasoned caddies who set the standard, mentor newer caddies, and help us deliver an exceptional experience to every guest who tees it up at Pebble Beach.
When evaluating claims about job security, I encourage everyone to look at our track record. Over two decades of growth, opportunity, and investment in this caddie program provide a much clearer picture of our intentions than speculation ever could.
On this note – some facts specific to another program most similar to PB’s – Whistling Straits, employment-based with a Seniority system/tiered pay/Activity Bonus’ where 58% of the jobs carried out are by Tier 3 caddies (Veterans); 50% of those Senior caddies have been with us 10 or more years; 21% have been with us 20+ years. Year-end activity bonus’ distributed in 2025 amounted to $97,000. Pretty important facts – not propaganda.
I appreciate your attention to this note – Dan
How much are caddies making as employees? Take a look at an actual caddie’s experience:
INVEST IN YOURSELF — NOT UNION DUES
If you’re planning to work as a caddie for the next 20 years, you could end up spending more than $12,000 in union dues. What if you put the same amount in your new 401k with a company match? You’d have saved tens of thousands of dollars for your retirement.
The New Standard of Caddie Excellence
- Identical Take-Home Pay with Massive Upside: While base “cash in pocket” per loop remains virtually identical to the contractor model, employees receive over $9,000 in additional annual value through benefits and savings.
- Immediate Tax Savings: As an employee, the company now pays the employer’s 7.65% share of Social Security and Medicare taxes, which saves an active caddie approximately $3,300 per year compared to being self-employed.
- Retirement Security with “Free Money”: Employees are eligible for a 401(k) match where the company contributes 25% on the first 5% of your savings, providing a guaranteed boost to long-term financial security.
- Paid Sick and Safe Time: Unlike independent contractors who only earn when they walk, employees now accrue paid sick leave (up to 80 hours per year, with up to 40 hours carried over annually), providing essential income protection during illness.
- Comprehensive Injury Protection: Caddies are now fully covered by CADDIEMASTER’s Employee Workers’ Compensation, ensuring professional support and financial coverage if an injury occurs on the job.
- Guaranteed Reporting Time Pay: If you report for a scheduled shift and your loop is cancelled or you are not assigned work, you are now guaranteed “show-up pay” for your time.
- Legal Overtime Earnings: Employees are eligible for overtime pay at 1.5x or 2x their regular rate for long workdays or working seven consecutive days, as mandated by California law.
- Elimination of Work Expenses: The company provides a $30 monthly cell phone allowance and supplies all required uniforms and tools free of charge, removing costs that were previously paid out-of-pocket.
- Access to Protected Leaves: Employment provides a safety net for life events through California Paid Family Leave, Bereavement Leave, and Personal Leave, allowing caddies to prioritize family without losing their position.
- No Monthly Union Dues or Fees: Under the new model, caddies maintain a direct and collaborative partnership with management through an “Open Door Policy,” ensuring that 100% of your earnings and bonuses stay in your pocket.
- With You, Not Just For You: Continue our Phase Meetings, started in February, where all who want to attend can share thoughts, suggestions, and feedback directly with CADDIEMASTER. Together, we can Be Better.
TESTIMONIALS
“Good morning, I got paid direct deposit and I am so satisfied. It was more then I added it up to be also. I am so happy about this new employment model.”
May 22, 2026
“Working at our club has been a life-changing experience. From creating strong bonds with the members and golf staff, to observing a championship golf course built from scratch, CADDIEMASTER has gone above and beyond to make a transformational caddie program with other passionate caddies who are devoted to the game of golf. There was skepticism about what the new management would look like, and all of our caddies who stayed thru the transition have no regrets and we now have an outstanding caddie manager who individualizes everyone’s outside life needs while balancing what feels like unrealistic expectations on a day to day basis. This will be my 30th year as a caddie, 10th season at the club, and by far the best caddy experience I have ever been a part of, that is only getting better and more legendary. I am grateful to CADDIEMASTER for protecting the community that was here before they arrived, and how the management has embraced us, and helped us become more successful.”
John M.
“Working as a caddie can be tough due to the uncertainty that comes with each day. Traditional caddie rooms are often handicapped by seniority and reputation, which makes it harder for new caddies to gel. Sometimes, you wait around all day for work that isn’t even guaranteed, while other caddies continue to get their daily loops. Other times, things outside of your control happen, and you get bumped to the back of the list for work that day. In my experience, working for CADDIEMASTER has made these issues nearly nonexistent. Rather than feeling like a lone animal fighting for a spot at the watering hole, you feel like you’re part of the pack. There is a sense of structure that is felt from the new hires all the way up to the managing staff. A standard is created and echoed throughout the caddie yard, and while it has taken time to build, I have seen what a group of good caddies can become — even beyond the golf course. It all stems back to the culture being curated by the ones running the show.”
Brayden N.
“As a caddie who was there before and after CADDIEMASTER, I wanted to say a few quick things. First of all change can be scary, I definitely get that. Especially when you’ve been somewhere for an extended period and are used to doing things a certain way. I wasn’t sure how this new company would treat someone who wasn’t recruited through their process. I’m glad I decided to stay the course. Not only were they supportive but extremely encouraging as well. The work was and has remained steady and being a familiar face to the membership in a time of transition can go a long way. Requests have increased and our management team works hard on every aspect of our behalf daily. If you’re on the fence about sticking around, my advice would be to give it a try. I’m glad I did.”
Tom B.
“Switching from an independent contractor model to an employment based model has been a substantial improvement. Clear and consistent policies along with a structured schedule have improved every aspect of our program. We’ve been able to further integrate our caddie program with the club and it has led to a mutually beneficial partnership.”