craig headshot Small Business Coach, NY

free small business ebook career coachStop Playing Small in Your Business!

Why Do Small Businesses Stay Small?

Download this free guide and see if you're making any of these growth-stopping mistakes that keep small business owners from truly growing their business.

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Partner With an Expert Coach

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You may be thinking "Is he qualified? "Will he be a good fit for me?" Find out about my approach to business coaching, my experience and what clients say about me.

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Choose a Coaching Program

craig jennings executive business coaching

Ready to stop thinking like an employee and start working ON your business? Choose a business coaching program that matches your needs and prepares you for growth.


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Get a Speaker For Your Event

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Have Craig speak at your event. You'll get a small business expert who loves to share and speak on topics such as small-business problems, solutions, difficulties and rewards.

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Welcome to Craig Jennings, Business Coaching

There is a reason why small businesses stay small, and it has everything to do with the owner. If you are ready to stop playing small, and achieve the growth you envisioned, you have come to the right place. Growth is not always comfortable – it has its challenges, which many small business owners avoid. If you want to confront the challenges, I’m ready to help you discover where and when your growth efforts may be. Craig Jennings has been named one of the top small business and career coaches in the country. He’s been coaching for 15 years now, and you’ll find his wisdom, advice and help to be second to none.


Craig graduated from Harvard College and attended Columbia University for graduate studies., He is a self-proclaimed entrepreneurial junkie, successfully starting eight businesses on his own, including a high-tech computer training center and an award-winning advertising agency. He also worked as a commercial diver in South Africa for 7 years and created “Undersea Associates.” He and his crews worked on drill rigs, performed underwater hull cleaning, and deep mixed-gas diving, to 600’, as well. Craig is an internationally recognized business and leadership development coach, Ask him for some of the 10 reasons why small businesses stay small! This is a very interesting inquiry for the businessperson looking for growth. (You’ll find some of the 10 reasons on his website.)

Merging energy and enthusiasm into his coaching practice, Craig provides his small business and entrepreneurial coaching services as a partnership, working with you on every aspect of your business. You’ll never be left wondering what the next steps are for growing your business. With Craig Jennings, you will receive all of the coaching and training you need, as well as advice, support, encouragement and accountability.

You Want Growth?

If you are looking to grow your business quickly and achieve significant results, contact Craig today for a free consultation. Craig Jennings, Business Coaching offers businesses and start-ups a set of packages to choose from, dependent on the needs of your brand. With hundreds of success stories, there’s a reason that companies choose Craig Jennings as their expert coach to fulfill their definition of success.

Your Business, Your Growth

Get started with Craig Jennings and see the difference that business coaching can make for powerfully growing your small business. For more information, please call (516) 944-6454 or use the email contact form to get in touch.

Articles To Help You and Your Business Grow!

  • Conversation with an Entrepreneur
    Jerry from Texas was a member of my mastermind group. He was an internet wizard, self-employed and described himself as “busier than a cat in a sandbox.”  (colorful Texas aphorism) It seemed he wasn’t getting as much accomplished as he wanted to, despite a heroic work ethic. I asked him…
  • Punctures on the Road to Success
    PUNCTURES ON THE ROAD TO SUCCESS – a coaching story about growth. Why the quick-fix approach to problem solving will leave your life in tatters.
  • Improving Marketing With Productivity
    The question, “What is Productivity?” has been present for me for over forty years. It's been a search. I somehow knew that productivity was the key to overall success. I define productivity as “Doing something worthwhile, striving to do it well and achieving a measurable goal that is intrinsically fulfilling.”…
  • What is CEO Time When It Comes To Time Management?
    Did you hear about the CEO who had a $300/hr bookkeeper? Ask a CEO or Small Business owner how he divides his time between CEO work, managing, and "Chief Employee" work (where he actually does work an employee could do.)  Most will say "10%, 40%, 50%" It's likely that many…
Read more articles...

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Today, I have several brand new clients, my team is expanding and my boyfriend has become my fiance! My business no longer runs my life, my client base is growing and my earnings are increasing. I have fulfilled my definition of success."
- Jennifer Brightbill, Seamstress

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