Expert's Guide to Evaluating Software: Chapter 1


Are all software companies the same?

After 20 years working in enterprise software, I thought I had it all figured out. Over the last year though, I’ve realized that software has changed but the evaluation process hasn’t. I was speaking with a division of a Fortune 100 company seeking to improve their manufacturing processes through new software. When they showed me their software comparison matrix, every vendor checked the same boxes. What?

Is all software the same?

Feels like it. So, if we all check the same boxes why do business outcomes vary so widely? What is really driving value and success for a business?

It’s common for companies to devise a list of critical features in a matrix or grid by which to evaluate different solutions. As such, us software vendors busy ourselves chasing the next feature, building frantically to “check” more feature boxes than our competition. And to what end? If everyone’s doing that, how do you distinguish good from great software? Or which solution will meet today’s needs and the unknowns that lay ahead?

Beyond the Matrix: Today’s Savvier Software Buyers

If you think about it, software constantly evolves. So, a software feature comparison today is inaccurate typically by the time a company has it rolled out.

Do phones have the same features today than they did 15 years ago? Or even 15 months ago?

Clearly not.

Given feature matrices limited value, it’s no surprise that a vendor’s feature set is receding as the primary method that companies use to select software. Some buyers are getting smarter; they are looking behind the curtain and shifting their evaluation focus to the actual software delivery method:

  • Do I install the software on-site?
  • Does the vendor host it?
  • Is it multi-tenant cloud or single-tenant/private cloud?

Oh, and there’s one last question: what the hell does any of this really mean?

What Really Matters?

The heart of the answer is flexibility. Is the software agile enough to keep pace with the accelerating demands of the business and the market it serves?

A focus on flexibility can be the beacon to guide companies through the noise of rotating software buzzwords. And contradicting rhetoric around them.

I’ve had the great fortune to have a front row seat during the birth of Software as a Service (SaaS or Cloud) as an early member of I supported hundreds of enterprise deployments and software evaluations during my long tenure there, and for the past decade at Veeva Systems. I’ve watched first hand as companies achieve long term success and moving a lot faster than they ever thought they could using cloud software.

Given the amount of mystery and misunderstanding about cloud software, I feel compelled to share my experience to uncover what really matters when making software investments. Over the next few weeks we’ll be releasing posts that look at this question from several angles to equip software buyers with the context and questions they need to select truly great software. Because truth be told, we’re not the same...not even close! 

Expert's Guide to Evaluating Software Series:

Chapter 1: What Really Matters When Making Software Investments
Chapter 2: Defining Software Models
Chapter 3: Security & Scalability
Chapter 4: Total Cost of Ownership
Chapter 5: Innovation
Chapter 6: Flexibility
Chapter 7: Conclusion
Chapter 8: 20 Questions You Should Ask Vendors


Frank Defesche began his software career at Trilogy Software in Austin, TX, an on-premise software company. In the summer of 2000 he joined as one of their first consultants. In a world dominated by on-premise and home grown software, he was faced with the challenge of translating traditional software processes to an emerging cloud paradigm. He was part of the cloud’s first chapter and has lived it ever since. He currently serves as the SVP and General Manager of Veeva Systems and is responsible for expanding Veeva’s solutions to industries beyond Veeva’s life science beginnings.


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