Strategy Career Questions (Part 2 of 3)

January 4, 2019

Dear Strategy:

“How do I evaluate a job opportunity that moves me from SaaS products to on-premises products but is one of the CEO’s initiatives?”

The first thing we need to do before answering the core of this question is to level-set on a few definitions…

“SaaS” stands for “Software as a Service” and is a term that refers to any cloud-based software product that is sold on a subscription basis. Of course, like most things, there are actually a few different variations of SaaS products, with the most typical being a piece of software that is both hosted and accessed completely in the cloud. So, there should be nothing to install on your computer and no need to download any updates, but there is also no way to access the software if you are somehow offline. Another variation of this model is software that physically resides on your computer or device, but that requires some sort of a subscription service to give it full functionality. Some mobile apps use this type of model, as well as some traditional software packages that could not effectively function solely as web-based applications.

On the other end of the spectrum is what might be referred to as “on-premises” software. This is the more traditional type of software product that is installed on and run from a user’s computer. Admittedly, the term “on-premises” might more commonly be used in a business-to-business context, but it technically refers to any type of software that is installed and run from an onsite device rather than in the cloud.

Needless to say, SaaS is the newer model and, as such, could be considered to be the trendier way to deliver software – particularly by those who are on the supply side of the equation. So, I completely understand how moving from SaaS to on-premises products might be perceived as taking a step backward from a career standpoint. But I also have to say that I’ve never been a fan of following trends, mostly because they’ve already been done. And, believe it or not, sometimes moving back to something that’s tried and true can actually be more of a breakthrough move than following what’s currently popular.

As an example, I mentioned in the previous blog post that I am a huge fan of music technology – especially synthesizers and electronic keyboards. Way back in the 1960s when the first analog synthesizers came to market, they were truly breakthrough products. Of course, as time went on, synthesizers moved to all digital and, by the mid-to-late 1980s, that had become the latest trend. Fast forward to just a few years ago and suddenly the analog trend was making a comeback – mostly because the sound and accessibility of that technology had once again become in demand by consumers. And those handful of synthesizer manufacturers that were the first to re-embrace this once-ignored technology (who, by the way, were also the same manufacturers who never really left it in the first place) were considered to be pioneers once again.

The point is that, even though everyone is jumping on a particular bandwagon, it doesn’t mean that bandwagon is always the best option for consumers. Personally, I hate the SaaS trend. Call me old fashioned, but the number of technology companies that are holding me hostage on a monthly basis for software that I only need once or twice a year is becoming increasingly frustrating – not to mention prohibitively expensive. And, on the rare occasion when I do need to access these products, if my Internet connection is down or I’m not connected to Wi-Fi, then I am plumb out of luck.


…even though everyone is jumping on a particular bandwagon, it doesn’t mean that bandwagon is always the best option for consumers.


Of course, that’s not to say that you should steer clear of SaaS products as a career just because I’m not a fan of them! But I would definitely advise against making any career choice based solely on what you think is popular. Instead, I would go in whatever direction your heart and your passion take you. If you love the SaaS world, then, by all means, stay with it (and, for goodness sake, please find a way to make it better for your customers)! But if you are truly passionate about the on-premises product, then I say go for it – and find a way to make that product better for your customers as well.

OK – seems maybe too obvious an answer, so let me make one other point before I go…

In this question, the CEO’s preferences were somehow introduced into the equation, leading me to believe that this factor might play some significant role in the decision-making criteria. Now, I’m sure that this next statement may be considered by some to be bordering on corporate blasphemy, but, at least in my opinion, the CEO’s preference is not something that I would personally base my career decisions on.

Yes, the CEO runs the company, and, yes, he or she will certainly have strong opinions about which roles employees should or should not be playing. However, at the end of the day, leaders want their team members to succeed. If you are offered a role that you don’t think you’ll be successful in, I can almost guarantee that your CEO would not want you to take it. And, in the end, the only person who will ever really know that is you.

You have to go where your heart tells you to go. You have to follow your passion. If you don’t, your chances of success are going to be exponentially reduced. And no CEO that I know of would ever want that to be the end result.

I feel that I have had a pretty successful career – and without going through my entire resume (which, if you’re so inclined, you can find here), I can tell you that I have refused no less than 3 positions that my CEO at the time wanted me to take. And the reason for each of those refusals was that my heart simply wasn’t in it. I knew that taking a job I really didn’t want would inevitably translate into causing more harm than good for my career – not to mention for the company. And as it turns out, each refusal (which I approached both humbly and respectfully) ended up opening doors to other, even better opportunities that I was truly passionate about, and that I ultimately turned into successes.

Of course, that’s just my story – but it’s a story I have seen played out many times throughout my career – both for myself and for people who have worked for me. So, all I can do is offer you the benefit of that experience, which, by the way, has always guided me to follow my passion. And that passion has yet to lead me astray.


Listen to the podcast episode
Dear Strategy: Episode 072




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Bob Caporale - Host and Author of Dear Strategy Podcast and BlogBob Caporale is the founder of Strategy Generation Company, the author of Creative Strategy Generation and the host of the Dear Strategy podcast. You can learn more about his work by visiting

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