A Sales Guys Perspective on the Modern IT Leader

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!


It’s Not What You Say, It’s How You Say It

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.

You Might Be Ruining Your Career and Not Even Realizing It

Let me start this off by clarifying what I mean by “ruining your career”. If you picked sales as a career, it says a few things about you. You’re a risk taker, money motivated and work is life. With that said, the WORST thing you can do as a sales rep isn’t missing your quota, it’s picking the wrong type of company.

Simply put, you need to pick companies that sell a true enterprise wide application that will allow you to sell deals with a high ACV (average contract value). If you don’t, you’re never going to make a life changing amount of money, you’ll just be a piker (a gambler who only makes small bets). The reasoning behind that is simple, higher ACV demands higher commissions and more skill. It’s also much riskier operating in an enterprise sales environment. Convincing a company with 10,000 employees to change their software strategy is incredibly challenging. It’s easy to sell a $1,000 widget that only impacts a few employee’s, it’s hard to sell a $1,000,000 enterprise wide application that changes the way 1,000’s of employee’s work. You work in sales because you’re a risk taker and money motivated though, right?

If you’re reading this now and you work in sales at a company that offers a point solution with a low ACV, GET OUT!


Keep in mind, nobody starts their career closing 6 figure and 7 figure deals. You’re likely going to start closing really small deals, likely in the thousands of dollars range. That’s completely OK! As long as the company you’re working for has a path for you to become a true enterprise sales reps (6-7 figure deals) then you’re in good shape.

There’s a reason why companies like Salesforce, Adobe and Medallia consistently produce sales reps with $1M+ W2’s, and it’s because of their ACV. Do you think they want to hire a guy / girl whose only sales experience is in selling small deals? Hell no.

Now you might be thinking, “how do I get into an enterprise company if I work at a company with a low ACV”? To be honest, it’s going to be challenging. You are going to have to accept that you may need to pay cut in year 1 and an initial step back in your career so you can take 2 steps forward. It’s going to be hard, really hard, but if you commit to it and you’re successful, you’ll be wondering why you didn’t do this earlier.


Deep Learning Demystified

“Deep Learning” is one of the buzz words we’ve all heard of but have no idea what it actually means. I’ve spent the past couple weeks learning more about deep learning to figure out what it actually is, and below is a quick digest that’s hopefully simple enough for anyone to understand.

At it’s core, deep learning is simply pattern recognition. Think of it as pattern recognition on steroids.

Neural networks are a set of algorithms, modeled loosely after the human brain, that are designed to recognize patterns. They interpret sensory data through a kind of machine perception, labeling or clustering raw input”.

^^ What on earth does that mean? Below is an example that should break everything down for you.

With a neural network, we are trying to solve – in essence – a classification problem. So let’s say you had a million images of dogs in a database of 3 million pictures (the numbers are just random). If you label each picture as “Dog” or “Not Dog” a neural network (as well as other possible algorithms) will try to extract the features from all the dog images as well as all the non dog images so that if you give it a new image, it can try to figure out what whether or not it is a dog. This is what we call a “feature extraction” problem. For example, with dog images, we might quantify features such as color, # of pixels, # of triangles making up the middle of the face, and any other thing we can think of. The algorithm will look for patterns in these features in your new image. Of course, the more exact our features and the better we clean our data, the better our neural network will work.


Input is a pixel, hidden layers are the progressions (ears, noses, triangles), output layer is a dog

Deep learning tends to layer neural networks on top of neural networks in order to better grasp patterns in the data. This can have issues such as model overfitting. Deep learning tends to function in an unsupervised environment. For example, in our dog picture example, we would not have captions for the pictures. The computer would be essentially trained to recognize features and group them. The computer doesn’t know what a dog is, all it is doing is grouping sets of features together. If our data is clean and we have a large enough data set, it will group a new image of a dog differently than a new image of a car and we will have achieved the same result.)

The biggest challenge with deep learning is teaching the set of algorithms to find and expose the data you want it to. In the example we used above with dog recognition, the model would not be able to efficiently find dogs in the images unless it has “learned” all of the features of a cat. What that means is you need to expose your model to a ton of data in order for the model to work properly.

Now here’s why I think deep learning is so cool (and freaky at the same time). We’re eventually going to live in a world where everything you do is completely personalized to your likes / interests. We’re already seeing some of that today (Spotify recommending music, Facebook recommending friends), but as we continue to feed these algo’s with more data, and as the engineers behind the scenes continue to get smarter, the possibilities are endless.

There’s A LOT more I could get into, but this post will essentially allow you to answer the question “what is deep learning” at a high level.


Sales in the Year 2020

Everyone has got some hot takes on what the future of sales looks like, so I figured I may as well throw my hat in the ring. Below are the trends that I’ve been observing.

  1. The Death of the BDR (as we know it).
    1. From what I’ve seen, BDR’s are starting to become very overpaid. I’ve heard some companies paying their BDR’s as much as $90K OTE (on target earnings). That’s insane for a role that is requires 0 years experience and is not closing actual business. I think software will eat up BDR’s with the rise of tech like PersistIQ and Salesloft. I also think Marketing will rise up and being to own demand gen much more so than they traditionally have.
  2. Streamlined Evaluations
    1. There are over 200 marketing automation tools out there. How can a VP of Marketing make sense of all of that? A platform will rise to help companies make B2B decisions just like we’ve seen for hotels (Tripadvisor), vacations (Airbnb), restaurants (Yelp) and household chores (Thumbtack).
  3. Steak Dinner Sales on the Rise
    1. I keep hearing that steak dinner sales reps are dying and the inside model is the way to go. To define what a steak dinner sales rep means, it’s a sales cycle based on building a relationship with the prospect and earning trust. Due to the rise of “noise” software (marketing automation, auto dialers), B2B decision makers are more weary than ever to engage with a sales rep due to how many incessant emails / cold calls they receive every day. That’s why the sales rep who’s focused on relationship first and sale second will dominate.

So those are my three hot takes. I’m sure people are going to disagree with me, but then again, it wouldn’t be a hot take if it wasn’t a little controversial.

What Exactly is a Mentor?

If you’ve ever read an article on “how to be an entrepreneur”, 1 piece of advice that’s always in there is to find a mentor. Well, what does that actually mean? How do you find a mentor and what purpose do they actually serve?

Those questions eluded me for years so I figured I’d share my thoughts on the role of a mentor, how to find them, and how to keep them engaged as well.

First things first, you need MULTIPLE mentors. Not just one. I doubt you’re going to find 1 person who will deeply understand every single facet of what you need help with. You’ll need what I like to call your personal board of advisors. I personally have separate mentors that I turn to with life issues, sales issues, career issues and a few other things.

Now let’s define what a mentor is. A mentor is not this Godly figure that swoops down from the heavens and know exactly all the answers to your challenges are. A mentor is an experienced and trusted advisor with specific subject matter expertise. With that said, I consider some of my close friends mentors because they have great experience in certain things.

How often should you engage with mentors? Unless it’s a close friend of yours, I’ve found that once every 30 – 90 days is appropriate. You need to keep in mind that these folks are incredibly busy and also have a life of their own to manage. When you do lock in a time, make sure that you come prepared with a very specific agenda and ALWAYS express your gratitude for their time, it goes a long way.

Last, how do you find these elusive mentors? The first step is find someone you admire and want to emulate. Go to LinkedIn, search the title of a person you’d like to model yourself against or that you believe has expertise in an area that you’re weak (let’s say CRO as an example for a title), and pick the people you believe to be most impressive. From there, go ahead and find their work emails and shoot them a note. Make sure you get across that you’re not looking to sell them on anything and are genuinely just seeking advice. You should literally make your subject line “All I Want is Advice”. Not everyone is going to respond to you, in fact, most won’t. I never said finding a quality mentor is easy 😉

So there it is, the mentor “mystique” demystified. Feel free to email me at kareem@ventureapp.com if you have any questions.


Office Politics

Having been in a fairly corporate environment for the past 3 years, I’ve learned a few things about how office politics works. I’ve had great mentors along the way who have taught me a lot, but there are some things I’ve had to learn on my own through trial and error. Below are a few things I’ve learned from my experiences.

You don’t need to be this guy to get ahead!


  1. Don’t share any personal details about yourself with colleagues that you don’t feel comfortable with the whole company knowing.
    • This includes what you share on social as well. Think twice about sending the 2:00 AM Snapchat to one of your colleagues (or anyone to be honest).
  2. They say don’t compare yourself to others, but your colleagues are your best measuring stick.
    • It’s no secret that the top performers within companies are promoted. With that said, identify who the top performers are and strive to be better than them.
  3. Office politics happens, but results trumps politics 100% of the time (at least in tech).
    • Age / tenure as a means for promotions is dead. You’re promoted based on ability and success.

I could probably add another 20 things to this list, but the 3 examples above are things I found to be most important. The biggest thing to keep in mind is that office politics exist so people can play certain cards to gain some type of advantage (promotions, pay raise or recognition). With that said, don’t get caught up in the gossip, try and have fun and make sure you do your job to the best of your ability.

How to Nail Your Interview

Having interviewed dozens of people and having been interviewed by a handful of companies at this point, I’ve learned a few things about how to nail an interview. Not to brag, but I’ve never walked out of an interview without having received a job offer, and I’ve even turned down a few jobs. The most important thing I’ve learned is that while being personable in an interview is important, your interview fate is really decided before you even show up.

It’s all about prep.

The more you prep, the higher the odds are that you’re going to nail your interview. Preparation indicates that you have a strong work ethic, which is the toughest thing to screen for in an interview and also one of the most sought after traits that companies seek. Below are the things that I do before every interview I have.

  • Website Research: Read every single page on your prospective company’s website. Focus in on any case studies, customer testimonials, or whitepapers that the company has published. This is a great way for you to learn the ins and outs of a business, and it’s also a great way to brainstorm some thought-provoking questions to ask.
  • Competitor Research: Google “[company X] competitors” and look into the top 3 that you see. Try to determine the strengths/weaknesses of each competitor and how your prospective company compares.
  • Customer Reviews: Google “[company X] reviews” and take a look at what consumers are saying. This is a great way to get insight into where a company is headed and how its functionality stacks up in relation to its competition.
  • Employee Interviews: Do a LinkedIn search for people in your current job role at the company that will be interviewing you, connect with these people, and send them a message. If I could only choose one way to prep for an interview, it would be this way. You’re guaranteed to find information through this line of inquiry that you wouldn’t have discovered in the interview process, whether it’s good or bad. I know it can be difficult to reach out to someone you’ve never met, so I’ve included a sample message below.
    • Hi [Name]. I hope all is well! I’m interviewing for [role Y] at [company X], and I’d love to talk to you to get some insight into your interview experience and what you think of your role. My schedule is flexible, so any time that’s convenient for you for a 30-minute chat would be great. Thanks!

All in all, the above process should take you about eight hours. This may seem like a lot of time, but if it lands you your dream job or a job above your pay grade, then you’ll be getting significant and clear ROI. There’s no substitute for hard work, but as the saying goes, hard work pays off.


How to Biz Travel Like a Pro

Having traveled for work 30+ times this year, I’ve learned a thing or two about the do’s and do not’s about biz travel. This isn’t going to be the cliche “travel light” BS, these are things I’ve learned from other folks and through experience.

  1. Wrinkle Spray.
    • This stuff is God’s gift. When I unpack my collared shirts, they usually look like they were soaked in water and wrung out. I used to spend a ton of time ironing my clothes when I got to my hotel. However, with wrinkle spray, all you need to do is hang your clothes and spray the solution on your clothes. 5 minutes later, no wrinkles. Incredible. 
    • http://www.amazon.com/Wrinkle-Releaser-Natural-Atlas-Travel/dp/B00P8GNO5E
  2. Hotels give you toothpaste/toothbrushes (usually).
    • Every hotel offers toothpaste for free, but you have to ask for it at the front desk. Most hotels will have toothbrushes as well, but they’re usually pretty crappy, so I suggest packing your own.
  3. Comfortable clothes for travel.
    • This may be more of a personal thing, but I hate wearing suits/collared shirts while on a plane or train. I always wear jeans and a t shirt. Especially on the way back. When you’re exhausted after meetings, putting on jeans and a tee VS a suit makes all the difference in the world.
  4. Invest in nice luggage
    • It’s just worth it. Trust me on this one. I suggest Rimowa luggage. It looks slick and lasts a lifetime.
  5. Have Fun.
    • After work is done, go out and explore! Don’t just got back to the hotel and watch TV. Get on Yelp, find some high rated bars/restaurants and go out. It can seem a little daunting going out alone in a new city, but that’s the start of a great story..
  6. Pedialyte (If you have too much fun).
    • If the night gets away from you a bit, and you’ve had 1 too many, drink a Pedialyte before you get to bed and you’ll wake up with little to no hangover. Pedialyte is essentially Gatorade on steroids.

Go Get It

Being a few years removed from school now, I’ve noticed a lot of people really hate what they’re doing, but stick with it because of the money. I get it, you’ve gotten accustomed to a certain lifestyle. You can buy nice clothes, you can go to the bars and take vacations whenever you’d like to. None of that replaces the sinking feeling in your stomach that you’re sort of wasting your life doing something you just don’t want to do for 60 hours a week.

Good news though, it doesn’t need to be that way. I love my job, and I often get asked what I’ve done to find a job I love. I live my life with a simple mantra, which is “Go Get It” and I apply that to everything I do, whether it’s my career or the gym. The only thing that is stopping you from getting what you want is yourself. I know that may seem like I’m oversimplifying things, but if you follow the 3 steps below, you’ll always get what you want.


  • The greatest innovators constantly live in a world of discomfort. Reason being, pushing new boundaries and exploring new things isn’t easy. There’s naysayers at every corner who are going to tell you to just stick with your doing and that change is a bad idea. This can come from family, your boss or most often, yourself. Don’t fall in the trap of being your own worst enemy, take action and get outside of your comfort zone.

“I’m continually trying to make choices that put me against my own comfort zone. As long as you’re uncomfortable, it means you’re growing”. –  Ashton Kutcher



  • Once you get out of your box, now you need to start working harder than you ever have. You’re going to fail. That’s a fact. But every failure gets one step closer to where you want to be. Anybody who is successful will tell you that it took a lot of failure, rejection and hard work to get to where they are today. 

“Failure is also a necessary experience for growth in our own lives, for if we’re never tested to our limits, how will we know how strong we really are? How will we ever grow?” – Arnold Schwarzenegger



  • Once you’ve gotten out of your comfort zone and worked your ass off to get to where you want to be, you’ve successfully gotten into a mind-set that will keep propelling you. What you’ll learn once you get to where you want to be is that you don’t want to stay there, you want to keep moving forward. Life is no fun when you’re in a rut. What is fun is seeing how far you can push the envelope.

“The tragedy of life is often not in our failure, but rather in our complacency; not in our doing too much, but rather in our doing too little; not in our living above our ability, but rather in our living below our capacities” – Benjamin Mays

To be honest, the 3 things I’ve described above are not that hard to do. It takes a lot of time and effort, but everybody has the capacity to do it. It’s not about intelligence or status, it’s about work ethic. At the end of the day, if there’s a will, there’s a way. Or as Shia Labeouf would say, JUST DO IT.