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How to ace your software vendor CEO interview

Brian Sommer Profile picture for user brianssommer June 17, 2018
Years of observation have focused our writer on the factors and actions that spell success for software vendor CEO candidates. Do you have what it takes?

the corner office
The corner office can be a tough place

With all the new CEO gigs being filled lately, I was wondering what it took to get one of those sweet jobs.  After a lot of consideration, I’ve distilled it to the following factors that separate CEO wannabes from the CEOs that get the gig.

So, if you’ve already refreshed the ol’ resume, here’s what you need to work on to nail that critical board meeting and win the top spot.

Pre-interview planning

Amazingly, a lot of CEO candidates are not as prepared as you might expect. Now is the time to finally open a Twitter account and use it to promote a specific social cause.  Better still, tweet and link to every social cause possible. You need to appear to be socially responsible and aware. Appearance matters!

Great candidates spend time cleaning up their Facebook page and make sure that objectionable content like sales kickoff party pictures are deleted and great social responsibility content is added.  Remember, your goal in this is to create the image of being a great leader – it’s the image (not actual deeds) that matter most!

You may also want to update your LinkedIn profile to make sure the phrases “value add” and “led by example” appear a few times.  Also, make sure you “Follow” only notable CEOs and a couple of noteworthy goody-goody types. Whatever you do, don’t follow any family (especially your worthless cousin that’s a roadie for a rock band that never made it), college frat brothers, or anyone else that knows the ‘real’ you!

Damage control

Like many candidates, you’ve probably amassed a few skeletons in the closet.  Did you:

  • Have a notorious affair?
  • Get spectacularly fired from a prior post?
  • Make an obscene bonus while laying off thousands of workers?
  • Promise product capabilities and delivery dates that no one could meet?
  • Get arrested for driving under the influence?
  • Grossly overpay for an acquisition that people are still talking about?

With each of these, figure out a way to spin them. Turn these negatives into positives. For example, the affair was part of a design thinking research session. The firing was due to a strategy disagreement with an activist shareholder. The obscene bonus was simply a side effect of your unending effort to unlock shareholder value. The layoffs were the unavoidable byproduct of your bold leadership in “re-energizing the corporate culture as the company prepared for the next step in its journey to digital pre-eminence.”

Sports analogies always win. That’s right - you made the tough game-time decision to right-size your enterprise. The acquisition was a bold swing at the plate, injecting the organization with badly-needed intellectual capital. Yep - you got this…

The story

Every CEO has to have a story/pitch. It’s their way of explaining what they intend to do (to/for the company) once installed in the big chair.  Now, if you’re not technical, don’t worry. Lots of enterprise software CEOs have bluffed their way into this gig.  How did they do it?

Remember the following rules for creating your pitch:

  • If you know the enterprise software space, you absolutely have to have a viable plan.
  • If you don’t know anything about enterprise software, talk about the capital structure of the firm.
  • If you don’t know anything about enterprise software or capital finance, then talk about the people and culture of the company.
  • If you don’t know anything about enterprise software, capital finance or the company culture, then get busy spinning a story about re-branding the company.
  • If you don’t know anything about any of this, talk in a fever pitch about “disruption”, “mobile-first” and the “consumerization of the enterprise.”

One of those should work.

The story in pictures

Now that you’ve got a story, you need to put it into a PowerPoint deck.  This exercise will pay dividends for the interview and for the first 18 months on the job.  Do it right and this becomes your go-to stump speech. You’ll use it with the board, key investors, Wall Street, industry analysts, customers, and prospects.

The key to a great stump speech is to avoid any specifics.  Whatever you do, don’t provide any guesses as to future earnings, revenue or other metrics. Those could come back to haunt you. However, do talk excitedly about a future liquidity event. Liquidity event discussions (e.g., IPO) are super strength caffeine for enterprise software boardrooms.

If you want to really differentiate yourself from other candidates, be prepared to discuss how you’ll wallet-frack the existing customers and extract more revenue from the install base without delivering any new product. Boards love that. You can also tell them one stretch goal you’ll insist the company have is to blow past the Rule of 40 and go for the Rule of 55. Then, show some humor and tell them you ‘can’t drive 55’.

Focus on jargon and catchphrases that you’ll repeat ad nauseam.  For example, you’ll want to make one of your anchor messages to be something like:

  • We’ll re-invent the future of work
  • We’re re-imagining the business of business
  • We’re the first true digital ERP firm
  • Others play in incremental change – we’ll transform businesses at scale!
  • We’ll compete at the speed of innovation
  • We’ll be the kings of cloud lift and shift
  • There’s nothing artificial about our intelligence!

Or better still, put three buzzwords into one super-combo message like People, Transformation and Digital. Ah, can’t you feel the auto-magical nature of this message coming together?

The best decks will have three parts. The first part must pay homage to the founders and all they’ve accomplished. This isn’t the time to throw the founders under the bus, though. You’ll want to save that for when you don’t make your numbers for the first time.  Thank them for their leadership one more time.

The second part is where you drop in your ‘story/vision’. Use plenty of pictures and few words for this. You want to be vague but still, you must sound supremely confident. If challenged, you should never concede anything. Instead, just reiterate your vision and double-down on the bet. The board loves executives who believe strongly in something even if they don’t fully understand it themselves.

The third part is what your short-term plans are going to be. Since you’ll be learning about enterprise software for quite some time, here’s where you tell everyone that you’re going to travel the world to:

  • Visit 100 customers in 100 days
  • Interview the top 50 executives within the firm (another 50 days)
  • Meet and greet prospective customers (another 50 days)
  • Assess the culture of the firm (another 20 days)
  • Meet with executives from channel partner and implementation partner firms (another 50 days)
  • Meet with venture capitalists, private equity firms, Wall Street underwriters, institutional investors, etc. (another 50 days)
  • Kick off the annual user conference, sales conference and, of course, the President’s Club sales event (another 15 days)

Before you know it, you’ve blown through a year or more and you’ve done nothing but go to meetings, check out a bunch of great restaurants, shake a lot of hands, etc.  It’s a tough life but you’re the man/woman for it!

Another part of your short-term plans will be the acquisition of your ‘team’. You’re going to claim that a different CFO, COO, and other executives are needed to “take the company to the next level in its evolution”.  And, it just so happens you know who these people are since you’ve drug them along to every other company you’ve been with. If these people are anything, they’re loyal. They may or may not be better than the incumbents but you know them quite well.

The attire

If clothes make the man or woman, it’s true for potential CEOs, too. Picking out the right attire is key if you want to project the correct amount of Silicon Valley coolness, MBA business smarts and a clothes style where you look 40 but are trying to appear like you’re 22.

For guys, you need to wear really skinny blue jeans, penny loafers with no socks, a shirt that can’t be tucked in, and a bit of hair product.  In fact, just so you avoid any potential for mistakes, throw away every tie you own except one red one (for weddings) and one black one (for funerals). A hint of a tattoo or a piercing doesn’t hurt either. At your next user conference, you want customers (and salespeople)  to know you can drink them under the table.

The extracurriculars

Now, any finalist CEO candidate needs to have those certain special extras on their resume. You’ll need at least two of these to become a serious contender:

  • You rowed crew at an Ivy League university
  • You’re already on the board of this enterprise software firm or on some other tech company
  • Your golf game is almost pro status
  • You’ve got a tight relationship with a major charity or social cause
  • You write open source software for a hobby
  • You collect lots of really pricey wines and fashion yourself as a bit of an expert on wine
  • You had a book ghost-written about some nuance of the tech world or in business management.

The interview

When you walk into that board meeting, you need to do it in style.  If you can’t enter via a skateboard, then at least wear a cape.  Alternatively, you can fly to the interview in a private jet/helicopter, or, better still, parachute onto the golf course where the board meeting is taking place. The entrance alone is 50% of your score.

Next, have your talking points down pat. If a director asks “What did you think of the weather last night?” you respond with “The best applications are designed for a cloud-first, in-memory based, consumer-oriented user interface.” Never ever veer off your talking points. Stay on message!

Never let any answer have less than three buzzwords. Every answer must communicate concepts like:

  • Actionable, real-time, augmented insights powered by machine learning paradigms
  • Continuous, permeable platforms designed for the integrated business existence
  • Self-driving machine tools with neural chipsets and 6G telephony abilities
  • Reimagined constructs propelling future business capabilities that only your customers will achieve

Post interview

Hopefully, you followed the above advice and got the job. Now, you need to focus on the employment contract. Well, that’s an all-together different article…

Note: No shareholders were harmed in the creation of this piece.

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