Tammy Alvarez is a visionary who catalyzes leaders to level up their performance for themselves and their businesses. Her spirited “Break all the Rules” approach blends decades of C-Suite experience on Wall Street with a pragmatic, results-based coaching style that helps business professionals create a big impact and love every Monday morning again. Her unwavering commitment to advancing ambitious business leaders compelled her to create the Career Winners Circle - a comprehensive collection of coaching and training programs designed to strengthen leaders so they can grow their careers as far as their ambitions will take them, and continue to thrive once they get there. 

Can you tell our readers about your background?

I spent nearly 30 years in the financial services and technology industry and the last 15 as a C-Suite executive on Wall Street.  After finally “making it” to the most senior levels, I looked around and thought “Is this really it?”.  Feeling bored and uninspired, I made the decision to cash out, move to a tropical island in Central America, and start a coaching business. It’s been the best and scariest decision I’ve ever made.

What inspired you to start your business?

During my corporate career, I saw too many talented people getting stuck on the sidelines, and seeing all that talent wasted drove me nuts. Having spent time in the board room and behind closed doors, I know how things “really work”. I wanted to share my knowledge and experiences so talented leaders can make better decisions and take more control over their careers. I want everyone to love Monday mornings and become the CEO of their career.

Where is your business based?

We are headquartered in Stamford CT and run the majority of our operations from San Pedro, Belize on a small island called Ambergris Caye. When we made the move 4 years ago it was way before covid and most people hadn’t heard of Zoom. People thought I was crazy. Now they’re asking me how I did it!  I traded one island for another in moving from Manhattan NYC to San Pedro, Belize. It’s been fun transitioning from SoHo to Bo Ho and trading in my Manolo’s for flip-flops.

How did you start your business? What were the first steps you took?

All the first steps I took were completely wrong. Welcome to the world of entrepreneurship! Coming from corporate I thought I had all the answers. Boy was I wrong.  I came up with a company name, formed an LLC, hired someone to do my logo, built a website, created offers I thought people would want, recorded videos, created an advisory board, and then when I was “ready” I started talking to people. WOW! That was the absolutely wrong way to get started. In hindsight what I should have done was start talking to people right away and to test my offers as soon as possible, despite the imperfections.  What people need and what they will buy are two totally different things. People who need you and people who like you are also different.  Figuring out your audience, their pain points, and their dreams are the first place to start. When you can layer your expertise into that equation you have a winning business.

What has been the most effective way of raising awareness for your business?

Word of mouth and social media.  A serial entrepreneur and dear friend gave me an important tip when I first started.  She said “Your friends and colleagues will not buy from you. Most of your customers will be strangers and you need to get out there and sell.”  She was right. 2% of my clients are people from my personal or professional past. Social media can be so frustrating because it seems like no one is watching (despite all the ads that say “1 sales funnel is all you need to earn a million dollars”).  What I’ve found is that it’s a necessary evil. When people find you, they want to get to know you before they reach out.  The more info you have for them to get to know, like and trust you during their cyberstalking – the more likely you’ll get that outreach when they have a need.

What have been your biggest challenges and how did you overcome them?

Making the transition from corporate exec to entrepreneur is probably the hardest thing I’ve ever done so far. Managing a 200M P&L and 2,000 people is so much easier than starting a company.  Making mistakes with your own money, learning an entirely new landscape, the loneliness of being a solopreneur, and finding a rhythm that was fulfilling and productive were really hard.  I overcame them by hiring a coach. Here’s what I learned (and am still learning).  Use the things that have worked for you in the past. Just because you’re in a new arena doesn’t mean they’re not valuable and useful. Give yourself significantly more time than you think you’ll need for absolutely everything. The time drain on a learning curve is significant. Find your tribe. I found a group of coaches that are amazing and we collaborate every week. Treat everything like an experiment.  There’s never a right answer and even if there is, the playing field is changing so rapidly you constantly have to adjust. Test all the time, adjust and pivot quickly. If something works, stop doing the other things and throw all your time and energy into that. Don’t let your mistakes define who you are to become. Use them to define how far you’ve come.

How do you stay focused?

Living on a tropical island where everyone is on vacation or semi-retired is difficult.  There’s always a scuba dive, catamaran, or pool bar crawl going on with our friends. I block one or two days a month to play “hooky” so I can stay focused the rest of the time without having too much FOMO. I also get distracted by shiny objects – the latest app, new tool, etc. I block my day and do the most important things first so I have time to play with new ideas later in the day.

How do you differentiate your business from the competition?

Results and approach.  My coaching style is more of a “coach-sultant”.  I spend a lot of time helping my clients chart their own paths. Because of my experience, I also tell them exactly how things are working “behind the scenes” in their company and advise them on what to do. This helps them move faster.  I keep quantifiable metrics on my clients’ progress.  On average my clients are getting a new role or promoted within 4-5 months and are earning 20% more. That’s an ROI that resonates with my target client base.

What has been your most effective marketing strategy to grow your business?

Sharing the successes of my clients, testimonials, and a strong referral and affiliate program. I celebrate my clients’ wins on social media and my clients join the Winners Circle. Most prospective clients I speak with mention the fact that they want to be on the winner board too.  Acknowledgment is key and when you celebrate your client’s win you are also demonstrating your ability to deliver results without being too braggadocious about it. Testimonials are also key. Social proof that you’re the real deal produces a massive uptick in new clients.  While most of my clients refer their friends and colleagues without expecting anything in return. I always have a financial or service-based thank you for their loyalty. I am starting to rely on other coaches who serve my target clients in a different way.  They become affiliates and we get to the point where we cross-refer business. This approach is working out extremely well at the moment. 

What's your best piece of advice for aspiring and new entrepreneurs?

Make sure you have enough capital for you and your company to survive for at last 3 years if you can. If you don’t have it – raise it. Starting a business is hard. Starting a business with immense financial pressure is even harder and will lead to a “ready-shoot-aim” mentality. I think it’s the reason why most small businesses fail.

What's your favorite app, blog, and book? Why?

I love Atomic Habits, Think Again, Marie Forleo, Radical Candor and the 5 AM club. These books and podcasts challenge my thinking and give me a new way to up my game. I am the only engine driving this business forward and I need to be in top shape so my company can succeed.

What's your favorite business tool or resource? Why?

I’m a huge fan of LinkedIn.  It’s a one-stop-shop platform for me to learn, contribute, and win new clients.

Who is your business role model? Why?

I find inspiration from other entrepreneurs who have “made it”.  Not necessarily the big guys but the everyday Joe or Jane who defied all odds to bring their dreams to life and make an impact on the world. Anyone who is ahead of me and has walked in my shoes has something I can learn from; which is why I love collaborating with entrepreneurs and small business owners.

How do you balance work and life?

I put life first. I have goals to grow the Career Winners Circle into a million-dollar company.  I can’t do that if I’m not at my best which is why life comes before work.  When life is enriched and fulfilling, I show up so much bigger for my community and am able to leverage the best version of myself.

What’s your favorite way to decompress?

Scuba diving. I am getting salty at least 1 morning before work and on the weekends each week. Any day in the Caribbean fish tank is a good day!

What do you have planned for the next six months?

Scale…scale…scale!  We have cracked the code on solutions that work and deliver epic results for our clients. Now we need to find more of them so more business leaders can love every Monday morning again.

How can our readers connect with you?

The best way for us to connect is through our contact page on our website https://careerwinnerscircle.com/contact/ or through LinkedIn at www.linkedin.com/in/tammyalvarez