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Learn the Secrets of
Successfully Selling to CIOs


If you sell technology to CIOs (Chief Technology Officers), you know getting their attention is harder than ever.

How can you break through the barriers to win their business?

Learn how to sell to the CIO.

David Silverstein and Randy Gaboriault go straight to the source—CIOs themselves—for insider insights on what works, what doesn’t, and what they wish salespeople would do differently. 


In this book, you’ll learn everything you need to: 

  • Make the initial connection. Email blasts, LinkedIn invites, and cold calls don’t work; here’s what does.

  • Be a partner, not a pest. CIOs are busy. Sleuth out info on their company and concerns without taking a second of their time.

  • Clinch the sale. You worked hard to earn that meeting—so don’t blow it. Here’s what seals the deal (and what notto do).

  • Build long-term relationships. Turn one sale into many by inspiring lasting loyalty from your customers. 

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Our Story

When salespeople and CIOs work together, great things can happen.

The co-authors of this book are a case in point. When veteran salesperson David Silverstein and CIO Randy Gaboriault got to know each other, they began talking about their experiences from both sides of the trenches. The pair quickly realized they had the makings of a book—this book—on their hands.


But unlike every other sales book you’ve ever read, this one isn’t full of tips from successful salespeople.
Instead, we went straight to the source—CIOs themselves—to gather insider insights on what works and what doesn’t when selling to them. After all, who better to advise you on selling to CIOs than the very people you’re targeting?

This book is ideal for Sales Reps & Managers, Client Executives, Account Executives, and anyone selling to technology leadership.  You'll learn how to sell to the CIO.  Find out what top Chief Technology Officers, Chief Information Officers, and IT Executives want to hear from IT Sales Professionals.

Join our Linked Groups for more discussion:

Selling to the CIO

Mid-Atlantic Technology Networking Group

Technology Sales Networking Group

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David Silverstein has spent the last 25 years in technology sales and leadership. David is a results-driven relationship builder who is fiercely competitive and passionate about his career. He prides himself on building highly cooperative, energetic competitive cultures. Over his tenure he has held positions in direct and channel sales, target and strategic selling, and most recently VP of sales for a large publicly traded systems integrator. 


Randy Gaboriault has spent the last 15 years as an award-winning, global CIO across multiple industries, from aircraft engines and automotive to medical devices and health-care services. 
CIO Magazine editor-in-chief, Maryfran Johnson, named Randy an “exceedingly rare, triple threat CIO: a CIO that is equally talented at managing, problem-solving, and driving revenue.” Randy has spent his career creating strategies for exceptional and differentiated technology-enabled value chains. With this experience has come thousands of interactions—good, bad, and ugly—with sales professionals and the sales apparatus of organizations large and small.

In the press


"The firsthand experiences shared in this book reveal the nuances you must navigate to fine-tune your capabilities and become a successful technology salesperson."


President, Reuters

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