Tammy Alvarez is an ex-Wall Street executive turned CEO of Career Winners Circle (CWC). She blends C-suite experience with no-nonsense coaching to help ambitious professionals escape burnout, reignite their teams, and fall in love with Mondays again. As an entrepreneur, keynote speaker, and best-selling author of Escaping the Career Trap, Tammy’s “Break All the Rules” approach has guided hundreds of leaders and companies toward sustainable success. Whether she’s exploring new cities or working from the Caribbean, Tammy leads the CWC team in delivering bold, measurable results—proving it’s possible to lead powerfully from anywhere in the world.
What were your initial years of growing up like? Tell us about your life before starting your Entrepreneur journey/venture/initiative.
I’m a small-town kid whose first “boardroom” was a borrowed sofa. When I was fifteen, life yanked the rug out: my dad left, and we were homeless. My mom, little sister, and I began couch-surfing with generous relatives and friends for months on end. Every borrowed living-room sofa became my situation room—I learned to negotiate space, share resources, and keep spirits high even when the food was short and generosity ran low.
College couldn’t happen right away, and the rent, wherever we landed, couldn’t wait. So while finishing high school, I juggled two jobs: a bank as the world’s peppiest teen teller and supermarket cashier until closing time, collecting leadership hacks from cranky customers and midnight inventory counts.
Fast-forward: Wall Street. I’d hopscotched across five industries and eleven roles, honing my skills as I went. By 35, I was running global transformations as a Managing Director. At the end of my corporate career, I was a COO and led over 2,000 brilliant minds in 35 countries. I loved every PowerPoint-packed minute… until I didn’t.
Cue the plot twist: one suitcase, a laptop, two notebooks, and a one-way ticket to Belize. From a beach porch where iguanas decide when the Wi-Fi works, I launched the Career Winners Circle. Today, I’m its CEO, a keynote speaker, best-selling author, and coach, helping leaders reignite their spark before life swings its brass knuckles.
Those early plot twists didn’t just pad my résumé; they tuned my radar for possibility. If a sofa-surfing teen can steer billion-dollar projects and then swap a corner office for purposeful work under the Caribbean sun, there’s no straight line you must follow either—only the one you start drawing the day you decide circumstances don’t get the final edit on your story.
Every industry that is now a large-scale, top-notch business once started as a small idea in the minds of entrepreneurs. What was that idea or motivation that made you start your business/initiative? What motivated you within to say YES, go for it!”
My “go for it” moment wasn’t a single lightning bolt—it was a slow-burn blaze fed by two ugly patterns I kept seeing from the C-suite down:
Talented people were getting sidelined. Brilliant analysts, engineers, and managers started their careers on fire, only to fade into quiet frustration when bureaucracy or a bad boss clipped their wings.
Business owners were becoming victims of their own success. Growth brought complexity; complexity bred chaos; chaos crushed the very spark that built the company in the first place.
After orchestrating a dozen turnarounds on Wall Street, I realized we’d all been treating the symptoms, not the disease. Engagement surveys, flavor-of-the-month trainings, and perk-of-the-week programs were just corporate bandages. The real issue? We were solving the wrong problem with outdated solutions.
I saw something else, too: whenever we aligned people’s ambitions with the company’s mission—really lined them up, gear-to-gear—profits soared and Monday morning felt like possibility again. Business success and employee fulfillment aren’t two goals to juggle; they’re one engine with two pistons. Ignore either, and the whole thing seizes.
That insight nagged at me on every red-eye flight and every late-night PowerPoint marathon. Eventually, the whisper got loud enough to drown out the comfortable salary: Fixing this is easier than everyone thinks—so go prove it.
My mission is simple: show leaders how to create workplaces where ambition thrives, talent stays engaged, and results follow naturally—no gimmicks, no buzzwords, just the right problem solved the right way.
Tell us something about your initiative or current role. What is it about, and what impact are you trying to make?
Amplify 360 is our answer to the talent-engagement problem everyone keeps treating with the corporate equivalent of duct tape.
At its core, the program tackles the real disease behind disengagement: the silent misalignment between policies & people systems, leadership standards, and individual aspirations. We address each pillar in a three-step roadmap—Amplify → Disrupt → Thrive—so teams move from polite compliance to unstoppable commitment.
What it is
A 90-day, coach-led sprint that rewires three leverage points most companies ignore:
- Policies & people systems – the rules and workflows that quietly drain energy.
- Leadership standards – the habits that signal “thrive” or “survive.”
- Individual aspirations – what each employee actually wants from their career.
Why it works
We synchronize personal ambition with business strategy, turning “talent management” into true talent leverage. When people see a clear path for their own growth inside the company’s mission, and they see why their work truly matters, performance soars.
Who’s behind it
A bench of fractional executives, advisors, and coaches who’ve all carried the profit-and-loss backpack themselves. Our team blends decades of senior-level experience with “been-there” empathy and pragmatic playbooks, so clients get battle-tested insight instead of theory.
The impact we’re chasing
We’ve watched brilliant people get sidelined and owners become victims of their own success because companies keep solving the wrong problem with outdated fixes. Amplify 360 proves that:
- People are the engine, not the obstacle.
- Business success and employee fulfillment are inextricably linked.
- Closing that gap is far easier—and faster—than most leaders think.
Our mission is to help organizations of every size swap disengagement for high-octane momentum, making Monday the best day of the week for the business and the people who power it.
Your journey and your vision are very inspiring, but are there any achievements or accomplishments you would like to mention?
Winning industry awards, hitting bestseller lists, and spotting my book blazing across a Times Square billboard were pinch-me moments—equal parts thrilling and humbling. But the trophies I brag about are the ones you won’t find in a display case:
- 500+ leaders who now wake up excited for work, 95 percent of whom landed roles that energize them within five months and earn about 20 percent more.
- 100 organizations that traded talent churn for double-digit jumps in revenue, quality, and retention—often inside a single quarter.
- Those split-second “wait, I can do that?” faces when a client dismantles their own ceiling and sketches a fresh roadmap.
Watching executives embrace discomfort, test wild hypotheses, and emerge with careers and cultures they never thought possible is more rewarding than any marquee spotlight I’ve ever stepped into. Those transformations are the real headliners of my professional life.
Would you like to share with our young budding women entrepreneurs the change you would like to see in the world if given an opportunity?
If I could wave a magic wand, I’d scrap the “grind-to-prove-your-worth” culture once and for all and replace it with a world where courage is the default setting, especially for women building something from nothing.
Here’s the change I want to see (and why I get out of bed every day):
- Ambition without apology. I want every woman entrepreneur to treat her boldest ideas like non-negotiables, not nice-to-haves.
- Success that feels like oxygen, not survival. Imagine companies where profit and personal fulfillment grow in the same line on the graph.
- A sisterhood that funds, mentors, and multiplies. When experienced execs, fractional leaders, and first-time founders swap playbooks freely, we all rise.
- Mondays people actually love. That’s not a tagline; it’s the litmus test. Fixing it ripples through families, communities, and economies.
So to every budding woman entrepreneur: Break the rulebook, build the company you’d be proud for your kids to work at, and refuse to settle for a version of success that drains your spark. When we lead that way, we don’t just change our businesses—we change the entire game.
Women are a growing force in the workplaces worldwide, standing shoulder to shoulder with their male counterparts. What are your thoughts about women leadership today?
Women’s leadership today feels like an undervalued growth market—the fundamentals are rock-solid, the returns keep outperforming, yet most investors (a.k.a. legacy leadership systems) still underrate the upside.
Momentum: Women now run just over 11% of Fortune 500 companies, up from 10.4% a year ago—a record high, but still proof that nine out of ten corner offices remain male-occupied.
Headwinds: The leadership playbook was written for a different era, so even high-potential women regularly hit an invisible “second ceiling” of outdated norms, biased succession pipelines, and growth-by-exhaustion cultures.
At Career Winners Circle, we see the same pattern inside our client companies: disengaged talent, frustrated leaders, and owners who’ve become victims of their own success. I believe when women master five power moves that strengthen their voice, quantify their value, and expand their influence, they become the organization’s secret growth engine.
My take? Women leaders aren’t a ‘diversity metric’; they’re an under-leveraged market advantage. When companies modernize policies, raise leadership standards, and align individual aspirations with business goals, women don’t just “keep up”—they out-innovate, out-engage, and out-perform.
What would you want to say to our young leaders/audience reading this?
To every emerging leader reading this:
- Treat your career like a business. Iterate fast, test hypotheses, and pivot when the data—or your gut—says the model isn’t scalable.
- Choose courage over comfort, daily. Momentum is made—or lost—in moments of hesitation.
- Measure what matters to you. Define your own scoreboard—purpose, profit, promotions, or impact.
- Build a power base. Surround yourself with people who challenge, sponsor, and elevate you.
- Reject the grind narrative. Design a career that fuels you—because drained leaders can’t inspire others.
- Remember: the system is improvable. Be part of the renovation crew.
Lead boldly. Learn relentlessly. And never let Monday feel like a compromise.
Get in touch:
Website:
https://careerwinnerscircle.com/
LinkedIn:
https://www.linkedin.com/in/tammyalvarez/
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