About Us

Island of Sales specializes in conducting consulting on the development and training of individual people as well as the training of entire sales organizations.

Together with our customers, we design long-term strategies to achieve the most advantageous sales performance. We develop, execute, incorporate and uphold our proprietary sales processes. Our database consists of techniques for sales process, impulse factors, sales reluctance, closing, goal setting, attitude trainings, relationship building, profiling and qualifying, prospecting, lead management, work ethic , professional development and much more…

Our client base spans market industries including Medicine, Finance, Marketing, Graphic Design, Education, Technology, and Software.

Please visit our Speaking and Consulting page for more specifics and to tell us your needs.


Jason DeAmato – CEO & Founder

When I graduated college the most important thing to me was my band. My job was in the way of me seeing my friends and playing guitar. I didn’t have the first clue about business, nor did I want to. It was ignorance at it’s best. Then I got this part time job selling orthopedic supplies. I had no idea I was working in sales when I first started selling those orthopedic goods back in 1998. All I was told was “go around to these doctor’s offices, be yourself and build relationships, show them the stuff, if they seem interested get their information and I’ll take it from there.” Looking back this job changed my life in ways I would not compute until years later.

If you had asked me what I did back then I would have said “I work with orthopedic and post-surgical equipment but I also play guitar in a band” or something like that. I would have tried to sound important and cool and mentioning sales didn’t seem to accomplish either.

Now if someone asks me what I do, I proudly say “I’m in sales.” I consider myself extremely lucky to say that. I found my calling in sales and I love everything about it. And even more than selling, I adore breaking down the process, teaching and inspiring salespeople to be the absolute best they can be. But first and foremost, educating people on what being in “sales” really is and breaking down the stigmas that have existed for close to a century.

When I see heads nodding in a crowd, I am at my happiest. As long as I get to continue this journey I will be eternally grateful.

After years of experience and failing a million times at a million different things, I am happy to share those experiences to help people succeed. I am grateful for every failure and success, and when it comes down to it, I just love “talking sales.” Almost as much as I love talking music.

Unfortunately nobody pays me to talk about music, so until that day comes. Sales it is.

Randy Bernard – Vice President

I was born and raised just north of Boston and followed in my parent’s footsteps into sales. After building my career mainly on the west coast, I settled back in Massachusetts with my wife Jamie-Lynn and our hilarious children, Gage and Logan. I currently run sales for a great software company in Boston.

While much has changed in the world around me during my career, there is one thing that has never changed; the existence of a quota. I am as familiar with having a quota as I am with breathing. I have had a monthly quota for every-single-month of my life for 20 straight years.

Everyone knows the stresses associated with a career, marriage or parenting but how about also having a “must-hit” quota that resets every 30 days for 240 months in a row?!?!

It adds up to a lot of pressure, especially when you take quotas very seriously, like I do.

Underneath the challenge of straight monthly quotas for two decades, I’ve accumulated some remarkable stories, uncovered many mistakes and learned valuable lessons which I look forward to sharing with you.

Having held every role in sales from the entry level to the VP, I believe that my hands on experience is my greatest asset with which to help other salespeople hit their goals.

A positive attitude and a killer work ethic can get you very far, but to be top of your class in sales it takes additional skills. I enjoy teaching those skills through sales training, motivational speaking and consulting and have fallen in love with helping people learn the art of selling.

Teaching someone how to increase their closing percentage, rebound from a slump or crush their number is what I love to do more than anything!


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