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It’s really easy to chase the shiny, metal object when picking the company that you want to work for. Hearing the buzz words like AI, Deep Learning, Natural Language Processing, etc gets us all pretty excited (and maybe a bit scared, skynet), but what does any of it actually mean in the context of that companies product? If you can’t break down, in a very simple way, what issue your company’s product is actually solving and clearly paint an ROI picture, then good luck convincing a CFO to buy your product.

That’s why I like boring industries. Industries whose products have traditionally been hosted on-premise or managed in some legacy manner and are moving to the cloud. There are a ton of examples of industries like this, such as telephony, data center, and cyber-security. Below are 3 reasons why you should bet on boring companies (especially as a salesperson).

1. Product Market Fit
   • When you work for companies that are carving out a new space, you have to convince your buyer that there is a need for your product. When you work for companies that exist in a large, legacy industry, all you have to do is convince them that your modern product is better than their old product. I’ve worked in both, the latter is MUCH easier.
2. Budget
   • It’s hard to explain the ROI of a product to a CFO if they don’t use something similar to that product today. No line item in the budget exists for that product, and you have to convince the CFO that this additional line item cost will save them money / make them more efficient (very hard). When you sell modern products in a legacy industry, the company you are selling to is most likely already using a product in your industry so they have a line item for it. Your product is a line item swap which makes the cost easy to stomach, and pretty much every CFO understands the ROI of migrating from an on-premise/legacy solution to a modern solution in the cloud.
3. Building a Career (More Sales Related)
   • Being an expert in a legacy industry that is going through cloud transformation is great for your career. While industry knowledge isn’t the end all be all in building a successful sales career, it certainly doesn’t hurt and competitors will always try and recruit you away simply because of where you work.

I mentioned industries migrating to the cloud a few times as what to look for when choosing a company to work for, but cloud migration isn’t the only thing when looking for big, legacy industries. A great example is the corporate travel space, which has been dominated by travel agents for decades but is now being disrupted by companies like TripActions who are cutting out the travel agents by providing corporations with a consumer-grade travel booking experience. In general, what you want to look for are legacy industries that are modernizing. If you have any questions about which industries to bet on, send me a note!

Having spoken to and worked with dozens of IT Leaders, I’ve learned that not all IT leaders are created equal and that IT has a much bigger impact on the business than most people realize. An IT leader isn’t just a person you call when your laptop breaks, IT leaders enable the business to more efficiently hit their enterprise goals by investing in solutions and ensuring their adoption. At least, that’s what they should be doing. “Legacy” IT leaders just pick “industry standards”, go to Gartner and fear change. “Modern” IT leaders understand change is coming and choose to be earlier on the adoption curve / take more risks to help their company grow. Below are 3 observations I’ve had on IT leaders.

Move to the cloud, or move out of the way.

• It’s mind-boggling to me that some IT leaders still invest the majority of their budget into hardware-based solutions. Not only is it expensive, you’re also consuming all of your teams time on maintaining hardware. I haven’t met a single IT person that enjoys working in the server room or upgrading a PBX, it’s also not efficient. Rather than having 90% of your time spent on installing, maintaining and upgrading hardware, move to the cloud and have your team focused on how they can better support the business’s high-level goals. From a financial, time efficiency and business efficiency perspective, it just makes sense to move to the cloud. If you choose to ignore the cloud, I guarantee you will be left behind.
• Sidenote: If you believe the servers in your basement are more secure than Google or Amazon’s cloud, then please message me as I would love to hear your opinion. 

No one got fired for choosing IBM, no one made a name for themselves either.

• Yes, choosing IBM, Cisco, etc is a “safe” choice, but good luck moving up or getting a CIO role if you’re the “Cisco” guy. You shouldn’t make decisions based on what the “safe” bet is, you should align your criteria to the enterprises goals and decide on what solution allows the enterprise to hit those goals in the most efficient way possible. Making “safe” decisions didn’t get your company to where it is now, and always going with the “safe choice” likely doesn’t align with the culture that your company was built on. I’m not saying go out there and invest in every startup you see, but give them a seat at the table when evaluating and you may be pleasantly surprised.

Your job is to make the business more efficient.

• In every deal I’ve won at Dialpad, part of the reason we were chosen is because we could save the business hundreds, if not thousands, of hours previously spent on maintaining hardware, a function that adds little to no value to the enterprise goals. Eliminating these hours, in turn, enables the IT team to invest in different projects to help the business grow faster (enabling sales, support, marketing, etc). On the flip side, in every deal I’ve lost, the company went with the “safe” choice because they didn’t want to partner with a “start up”. By the way, all the “safe” choice means is that the vendor has a lot of customers, not always the best gauge of if they’re a fit for your business. In my opinion, those IT leaders are doing their business an injustice, because rather than picking a solution that will help the business accomplish their goals faster, they picked the solution that’s “safe” because (in my opinion) they’re concerned about job security.

All in all, I think this is a great time to be an IT leader. I don’t think there has ever been a time in the IT function where IT has had as big an impact on the business as they do now. I think you’ll start to see some “Modern” CIO’s take on CEO roles because of how deeply they understand how the engine of a business works. Agree with me? Disagree with me? I’d love your opinion!

 

I was teaching a class at Northeastern last week on Sales and Building Champions, and a student came up to me afterward with an interesting question. She looked at me and asked “How did you learn to speak with such confidence? Do you have any tips?” My response to her was simple. It was that confidence comes from believing in what you have to say. If you believe in what you say, and deliver your message with passion, your audience will believe it as well. On the contrary, if you don’t truly believe in yourself or your message, how do you expect the audience to?

I’ve luckily had some great mentors over the years who have helped me get better at public speaking and presenting. Not very long ago, I had to present to a C-level exec at a Fortune500 company and I admittedly was pretty nervous about the presentation. I thought to myself, “What value can a 26-year-old sales guy add to a C-level exec who has more years of experience in his field than I’ve been alive?” When I told my mentor about this, he gave me some great advice that really stuck with me.

“At the end of the day, they’re no better than you. They’re human beings with opinions, just like you and everyone else. The fact that they’re sitting across the table from you means that they respect you enough to give you their time and they feel like you can add value. Now, you have to respect yourself enough to deliver your message with confidence”.

That piece of advice really resonated with me, and it’s something I think back to whenever I feel a bit nervous about a presentation. Whether it’s speaking to an audience of 500+ people, teaching a class or pitching someone really “important”, as long as you deliver your message with confidence and conviction, the audience will appreciate your point of view. They may not necessarily agree with it, but they will at least leave thinking about your point of view.

This skill is particularly relevant if you work at a startup in an undefined market. No one has heard of your point of view before, so you’ll need to truly believe in your point of view so your audience can believe it.

All in all, next time you feel intimidated talking to someone because of their title or age, just remember that they’re no better than you and that your opinion is just as valid as theirs.