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Q&A with Jeff Kaplan: Cloud and Next-Gen Software Influencer

By March 17, 2014Article

Editor’s note: This article in SandHill’s series profiling leaders in the software industry features Jeffrey Kaplan. As founder and managing director of THINKstrategies, founder of the Cloud Computing Showplace and host of the Cloud Innovators Summit series, Jeff has been ahead of the curve in predicting the rise of SaaS, cloud and the overall shift of the software and technology industry from a product-centric to a services-driven business model over the past dozen years. He helps startups and established ISVs, as well as investors and enterprise decision makers, capitalize on this market opportunity. 

Were you always interested in technology while growing up? 

Jeff Kaplan: When I was growing up the only kind of “technology” anyone cared about was dial-up phones, color TVs and transistor radios, unless you were in the A/V Club and dabbled in more nerdy stuff. My interest in the technology industry was sparked by the chaos created by the AT&T divestiture, which fueled a wave of new innovations around telecommunications. 

That event also made me more comfortable with my lack of technical training because it showed me how markets are shaped by other business forces that I could understand and help influence. As a result, I’ve been fortunate to recognize a series of transformative changes to the telecom market and IT services industry as a result of outsourcing, enterprise networking and cloud computing. 

What led you to establish THINKstrategies? What needs did you originally address and have those needs changed over time? 

Jeff Kaplan: In 2001, when most companies were retrenching from the failures of the first generation of application service providers (ASPs) and utility computing ideas, I founded THINKstrategies to focus on the business implications of the shift of the software and technology industry from a product-centric to a services-driven solution delivery business model. I firmly believed that a combination of macro-market forces, changing customer attitudes and technological advancements would push the industry toward software and computing services. 

The success of managed services and Software-as-a-Service (SaaS) served as the stepping-stones for the advent of cloud computing. Although the cloud now permeates nearly every industry, many software and technology companies still don’t know how to properly package, price, position and promote cloud services. And many CXOs within SMBs and large-scale enterprises don’t have experience procuring and managing these services. Helping vendors, customers and investors capitalize on the business benefits of cloud services is the focus of THINKstrategies’ consulting services. 

What led you to establish the Cloud Computing Showplace? 

Jeff Kaplan: I founded a Managed Services Showplace and SaaS Showplace in 2006 when there wasn’t another vendor-independent, online resource where customers could learn about these offerings and share best practices. I decided to merge the two sites together in 2010 as the cloud computing industry expanded and the number of PaaS and IaaS offerings multiplied. The Showplace is now the largest, vendor-independent, online directory and industry best practice resource center in the cloud market, with over 2,300 solutions divided into over 90 application, service, technology and industry categories. 

Your SandHill Contributor Profile page says you’re practically addicted to sports. Did you play a sport while growing up? What did you like about it? 

Jeff Kaplan: I played nearly every sport as a kid with the exception of hockey and soccer, which weren’t popular in my neighborhood. I swam competitively in high school, played basketball regularly in college, and today stay in shape playing tennis and cycling. I love the camaraderie of team sports and the single-minded determination and ability to react quickly that’s required in individual sports. 

Do you see any correlations between sports and the software industry?  

Jeff Kaplan: Team work, focus and agility are essential to be successful in today’s increasingly competitive software industry. 

What leadership attributes are required for someone to influence an industry? 

Jeff Kaplan: The ability to synthesize lots of information from various sources and translate it into meaningful insight that can help companies establish solid strategies, create timely solutions and take effective actions to capitalize on immediate and long-term market opportunities. 

What was involved in establishing the Cloud Computing Showplace and THINKstrategies? Did you have an established reputation in the software industry at the outset? 

Jeff Kaplan: Yes. I had a track record of success as an industry analyst at IDC, Dataquest and Meta Group, along with successful experiences with leading solution providers in the IT and managed services industry, which gave me credibility and visibility in the industry. 

What about funding? 

Jeff Kaplan: Given the unpredictability of the consulting business and the lag-time associated with getting paid in this business, being sufficiently capitalized is essential for long-term success. Because I’ve been doing it for over 12 years, I’ve also benefitted from ongoing relationships that have resulted in a lot of repeat business. 

Were there any setbacks or any unexpected bumps along the way? 

Jeff Kaplan: No, I’ve been fortunate to be aligned with a series of industry trends that have fueled the growth and success of THINKstrategies and the Cloud Computing Showplace. However, staying tuned into the realities of these trends rather than being caught up in the hype surrounding them saved me from many of the traps that others have fallen victim to and allowed me to serve my clients well. 

Growing up, who was your role model?    

Jeff Kaplan: My dad was and continues to be my primary role model because he had a worldly curiosity combined with a practical perspective about how to get things done in a way that could help others. 

Please name three software leaders and describe what you admire about their leadership. 

Jeff Kaplan: Louis Gerstner took over IBM without a technical background and was unfamiliar with the IT industry, yet was able to turn around a rapidly deteriorating situation by recognizing the potential synergies across IBM’s various business units and redefining the company’s mission from products to services. 

Marc Benioff’s practical business skills combined with his tireless evangelistic capabilities have proved that the SaaS model makes sense and can change the way organizations work. 

Jeff Bezos pioneered the eCommerce model and customer experience that inspired Benioff and repurposed Jeff’s internal operations to deliver a new generation of shared services that made the promise of utility computing a reality and spawned a new set of IaaS offerings in a broader world of cloud computing. Along the way, he ignored the pressures of Wall Street investors and made long-term bets that are just beginning to pay off. 

At the time you completed your SandHill Contributor Profile page several years ago, you said if there is anything you would change about technology it’s that “it is still too complicated and too often fails.” Is that still your opinion? 

Jeff Kaplan: Yes, and I’m too often the victim of these failures. 

What do software companies need to do to change this? 

Jeff Kaplan: Continue to evolve and fine-tune the technical aspects of their solutions and recognize that they are in a service business that requires a solid support capability to respond to customers’ ongoing needs. 

Please describe some successes you’ve had with THINKstrategies and with Cloud Computing Showplace that show how you have influenced the industry so far. 

Jeff Kaplan: On the user side, we’ve helped CIOs and their business unit counterparts better understand how they can leverage today’s cloud solutions to achieve their corporate objectives and create new business opportunities to gain a competitive advantage. 

We’ve also worked with a wide array of cloud vendors ranging from young startups to the largest players in the industry. We’ve helped the startups and established players develop their strategies, target their offerings, promote their capabilities, build their partner ecosystems and satisfy the needs of their customers. 

We also work with VCs and PE firms to help them identify investment opportunities, evaluate specific investment candidates and achieve their investment objectives. 

Will THINKstrategies also begin to focus on the Internet of Things? 

Jeff Kaplan: I believe the Internet of Things would not be possible without cloud-based infrastructure services that enable economical network connectivity and storage capabilities, as well as the powerful new cloud-based analytic solutions, which make it possible to interpret the meaning of the Big Data generated by the explosion of remote sensors and connected devices. 

We are very excited about hosting our third cloud innovator executive forum focused on the unprecedented business opportunities and challenges created by the Internet of Things, called the Connected Cloud Summit, on Thursday, September 18, in Boston. 

What motivates you? 

Jeff Kaplan: I am fascinated by the way technology changes our behavior and can reshape industries. And I’m energized by helping companies figure out how to respond to their customers’ evolving needs and expectations and achieve their business objectives. 

Is there anything about the software industry today that you would change if you could? 

Jeff Kaplan: Vendors need to embrace the long-term business benefits of SaaS, which can give them greater insight into how their customers actually use their solutions. This not only enables vendors to continuously fine-tune their current solutions, but it also helps them identify new solution opportunities. This data can also be aggregated to create powerful benchmarks and key performance indicators (KPIs) that can be of tremendous value to customers and build stronger customer loyalty. 

Jeffrey Kaplan is managing director of THINKstrategies, an independent consulting firm focused on the business implications of the on-demand services movement. He is also the founder of the Cloud Computing Showplace (, and the host of the Cloud Innovators Summit series ( He can be reached at 

Kathleen Goolsby is managing editor of









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