Big Company vs. Startup

As many of you may know, I made the jump from Cisco to run Sales Engineering for a small startup in the valley. Even though my gig at Cisco was awesome, I am confident this was the right move for me. I know there are a lot of folks out there wondering whether or not they should take the plunge (because it is a huge risk), so I thought I would talk a little bit about my thought process in making this move. 

I have always been a risk-taker. I love fast cars, snowboarding, skating, cliff diving… you name it. My wife always tells me I’m missing that little voice in the back of my head that says ‘are you sure you can do this?” So I guess you could say my personality is slightly unhinged to being with… but that’s only part of the reason why I love startup life.

 I began my career as a sales engineer at a startup in 2007. I was employee number 25 in a company based in Boston with a satellite office in LA (I was in LA at the time). I was the 4th SE hire, which was impressive for a company of that size, but the way the model was built we had two SEs in Boston and two SEs in LA. 

I had no idea what I was doing, but I loved it. 

I was getting in early to prep and spending time with the engineers to learn the technology and the industry late night. The days were long, the office was a dump, my sales team was a shit-show, and my commute was horrific… but I didn’t care. I was learning new things at lightning speed, living in the awkward every day, learning the iron-clad fundamentals of what it takes to be successful, and attempting (and succeeding) at doing things I had no business doing. It was fun. 

I have often reflected on what I thought made this absurd lifestyle enjoyable for me. Why on earth would someone do that for a few days and then not run for the hills? For me, the reason is the challenge, the opportunity for rapid career growth, and the love of the unknown. My then CEO had this great saying that we were all just “bozos on a bus”, and I like that. 

I can actually sum up why I love startups in one quick back-and-forth in 2008 with one of my early mentors. We were out for a “career lunch” which you need in your 20s at a startup because you’ve been working insane hours and there’s no money yet for a raise and your manager needs to give you a pep talk and discuss the “long run”. Anyways, I was baffled about how she knew so much and always seemed to have a plan. So after a few beers I asked her, “You seem to know exactly what you’re doing… how do you know it’s the right decision? Have you done this before? When do you know what the next move is going to be?” 

Her answer would forever change my outlook on business and life. 

“Matt”, she said. “I just make it up as I go along. I never know what the next move is going to be, I make the most educated decision I can and if that doesn’t work, we say fuck it and try something else”. 

That’s why I love startups. Big companies can take chances as well, but if a decision is made to change something there are many layers of bureaucracy that your idea has to pass through before it can be implemented. What I love about startups is, if your idea is better than the idea currently in place, your idea becomes the company idea. The opportunity is always there to swing for the fences and make a huge impact in a very short amount of time (not to mention the upside potential, but more on later). 

That said, startups are not for everybody… and even with the ability of extreme influence and upside, not all startups are something you actually want to do. My first gig was pure luck. I interviewed on a whim, got the job, and it turned out to be one of the most rewarding decisions I’ve ever made. It started me on the path to where I am today. The thing is, if I hadn’t been willing to put in 12 hours a day for 3 or so years non-stop, it would have been a blown opportunity. 

That’s the other thing, in big companies everything is already established… tried and true. You can just leverage what others have done before you to make yourself successful. I think of it as hiking in the jungle. Big companies have already cut a trail for you that you can get to the top of the mountain. The path is well-formed with benches and supply stops, but it’s a roundabout way that’s going to take you a while to traverse. A startup has a general direction to the top of the mountain… maybe a few people have cut back some branches here and there… but it’s essentially bushwhacking. You have a map and a compass so you know where you need to go, and the way is potentially much shorter, but you have to figure it out (and you could be heading in the complete wrong direction). No supply stops, no rest areas, just a general idea and a goal. 

So why did I drop one of the cushiest jobs I’ve ever had to go bushwhacking again? Because I love the hunt. I love just "figuring it out." I love working with a bunch of intrepid explorers in uncharted territory, blazing a trail where there’s never been one. New technology, new market, new challenges... I love trying something new and failing because failure helps you grow. I love trying something and succeeding, I love helping other people succeed where they thought they couldn’t. I love the camaraderie, the “everybody does everything” mentality. I love the possibility of a MASSIVE payout if we pull it off. I love accountability and transparency. I love the trust that everyone in it is working just as hard as the next guy. 

So should you drop everything you’re doing and go join a startup? I don’t know… like I said earlier it’s not for everybody. There is also the very real possibility that the startup you join will crash and burn… most do. I must have turned away at least 60 or so companies before I finally made my choice… Cisco is a great company and I wasn’t going to leave for just any ol’ group of kids with a good idea. Going with a startup is losing your safety net… but with great risk comes great reward. At this point in my life my wife and I are in build mode so we’re swinging for the fences. It takes hard work, sacrifice, and “balls like church bells”. I’ve only been in it two weeks and I'm working as hard as I’ve ever worked my life… and I love it. So I guess you have to ask yourself “am I willing to work my ass off and take that risk?” For me, that wasn't even a question because that's what I do. 

SE Fundamentals: Pregame Playbook

I get alot of questions around proper preparation for a call. This depends on the type of call of course, if I'm doing an eval wrapup it's going to be different prep than a demo, so for today let's focus on the demo. In how to make a compelling demo every time, I talk about how to keep the content fresh, but before you do any of that you need to know how to get some content in the first place.

A quick disclaimer to start this one off: A great call can be had under any circumstances. Some of the best calls I've ever done as a sales engineer have been completely off the cuff with zero preparation. At the same time, I've also been caught with my pants down not knowing something I should have to help close the deal. I'm not saying you always need to do this thorough prep, but it's far more likely that you're about to bomb your call if you haven't prepped than if you had. At the very least it won't be as effective.

Step 1: If your current sales engineering gig is anything like mine have been, most days you're most likely going to be doing more than one call per day (if not, you probably need a new sales rep). As all those prospective customers are going to be talking to you about the same thing, they're probably all in relatively similar professions. My area of expertise is network security, so the majority of people I'm going to be speaking with are somewhere on the "security engineer" totem pole; be it individual contributor role, manager, director, or CISO.

So, in the morning before any of my calls I take a look at my newsfeed for relevant content for the day. I use feedly, but there are hundreds of other aggregators out there that all do basically the same thing: go through your list of sites/blogs and bring them to you in a nice, curated list. Mine looks something like this:

Where to find said blogs you ask? Google my friend. I googled "top security blogs to follow 2016" and I got a veritable bevy of content. Don't just follow any douche with a megaphone and good SEO, make sure they're proper thought leaders in your industry.

Every morning before your calls for the day, spend 10 minutes and look at the top stories of the day for your blogs and find something to talk about. They don't have to be super in-depth, scholarly explanations of the issue at hand, more something interesting and topical to come to the call with to grab their attention. On calls you're always trying to establish yourself as an industry insider, so the more information you can come with, the more engaged your prospect will be. Plus you may learn something. Be interested, be interesting.

Step 2: Now that we have our topical factoid, it's time to move onto our prospect. Every deal is all about the who, so we need to first know WHO we're talking to. There are three places I always look for this (and in this order):

1. LinkedIn
2. Twitter
3. Personal Blog

The reason I do it in this order is I am purposely going from business relevance to personal relevance. Why? Typically, things we have in common business-wise are going to be more effective in the beginning. As the personal relationship progresses, we may find out we both enjoy hiking or cheer for the same football team, but in the beginning I'm looking for shared VALUES rather than shared hobbies. There's also a big difference between doing your due diligence and just being creepy, but we'll get into that later.

The first thing I look at on LI is shared connections. If we know some of the same people, it's a quick way to establish rapport. If there's nothing there, maybe something about their company is interesting. Do you know anyone who works/worked there? Do you know anyone who has given them a recommendation? How about previous companies? What about where they're based? Do you know someone who lives there? Have you traveled there in the past? What about companies they follow (if there are any other than the company they're currently working for)? I focus on these points first, as they're less cheesy in my mind. If none of these things pop, I move on to their college. To me, this is a stretch... because the chances that the person you know that went to the same school as your customer is slim to none... and your customer knows it. I never look at the skills they've been endorsed for or their groups, unless I want to pop it in as a tongue-in-cheek aside about the craziness of LI.

There are also those folks who have a skeleton LI profile... being in security I run into it all the time. So my search then takes me to Twitter and/or their personal blog. Twitter is a great place to get to know your customer... I look at it as a kind of halfway platform between professional and personal. Most folks will tweet about business-related issues, but with a personal touch on it. I'm not that guy who's gonna dig back through 5 years of someone's tweets, but I'll typically look back a few mos to see if anything relevant comes up (interesting retweets, opinions, etc).

Personal blogs, same thing. I don't have the time to read everything they've ever written in the <10 mins I have to prep before a call, but I'll usually have enough time to skim through a post or two.

I have heard of folks leveraging Facebook for prep as well, but I don't and I would caution you on this one. It's considered good form for a SE to do their due diligence on the normal business channels (LI, twitter, blog), but if you're not careful on FB you can look like a stalker... and nobody likes a stalker. In my experience, your prospect is going to be much more receptive to the fact that you were both interested in a recent news story or share a skill than a comment about his kids or something.

Also, as I mentioned earlier, make sure you talk to your Account Executive before the call. Prep work is only good if the subject is going to be receptive to it. Between the two of you, you should be able to get a proper plan in place. Also, in the many years I've been practicing these techniques, I have never once been called out for being too intrusive. On the contrary, most folks appreciate it. If my customer says something like "wow, you spent a lot of time researching me" I simply respond "Absolutely I do my homework. I want to make my demos as curated as possible, plus I like to know who I'm talking to so I can keep my comments relevant." The last thing your customer wants is just another generic commercial.

The last thing I do before any call is take a deep breath and clear my head. Sounds kind of silly and zen-ish for a tech guy I know, but there's a lot going on in my mind at any given moment, and the key to a good call is giving my customer my undivided attention. People on the other end of the line can sense if you're focused or not (ever get the sense someone is doing email instead of watching your presentation?), so stay focused.

Prep and focus... do it.



Anything else anyone likes to do before their calls? Drop me a line.

How to make a compelling demo every time

Demos are one of the core competencies of being a Sales Engineer. Every customer-facing SE has done at least one demo in their career... most of us learned how the business works by doing them. But, like everything we have to do that's repetitive, it can get old over time. I can't even tell you how many phone screens I've done over the years with senior SEs who tell me "oh, no... I don't do demos anymore... you don't have junior SEs or sales people who take care of that part?" Erm... no.

I believe it takes great skill to learn something new and to master it, but it takes FAR more skill to keep the edge sharp on something you've already mastered. To me, calling yourself a great SE and not doing demos is like saying you are an excellent pastry chef but you don't make the batter. Sure, sometimes you'll have a sous chef, just like occasionally you'll have a junior SE do a demo, but if you don't enjoy doing it, you aren't practicing the craft in it's entirety. 

Far more often than this, I run into SEs who still do demos, but begrudgingly so. And I get it... you're at an early or mid-stage company that's trying to train junior salespeople on how to book activity... and you're on your 5th unqualified, woody demo of the day. Trust me, I've been there... it's rough. By the time 3 o'clock rolls around you're getting a bit snippy with your AEs and you're slugging back that last cup of coffee you always regret. You probably have Facebook and a few other time-wasters opened in a browser window on your other monitor, thinking about your commute, wondering what your friends are doing... you're BORED. 

If you're at this point, chances are your demos have been fairly shitty for awhile now. Usually the first indication that you're heading in this direction happens shortly after you memorize your demo script and find your own spin on it that works (around 3 mos in, usually). Once you've found your groove, you start to get lazy and go on autopilot... then it's an avalanche of mediocrity from there. When you're lazy, you're not paying attention or asking the right questions. If you're not asking the questions, the prospect isn't engaged. If the prospect isn't engaged, chances are they're probably doing the exact same fucking thing you're doing right now... looking at a slideshow of the 10 worst child-star celebrity train-wrecks on buzzfeed or something. It goes without saying this is a MASSIVE waste of time for everyone involved, but how do you beat the boredom? How do you get excited about something you've already done hundreds of times and will probably do thousands more of before you're done?

The hard truth is, if you're bored doing demos it's your own damn fault... period. 

Some of the biggest mistakes I see SEs make are reading slides, not asking questions, and regurgitating the same content over and over again the exact same way. Don't get me wrong, the demo script is there for a reason, let it be known one of the keys to becoming a great SE is to read and memorize what others have built before you BEFORE you add your own spin to it. The reason for this is not so you can just chug thru the script verbatim for every demo you do, it's so you can nail down the CONTENT, then build variations on it to make it more compelling for the prospect. It's like riding a bike... you shouldn't do wheelies until you can ride in a straight line for a bit. 

So reading slides... I'm not going to belabor the point of how sleep-inducing this is, but if you have to read your own slides or say things like "as you can see on this slide", you may as well just put down your headset and go take a nap because that's what your prospect is doing. Instead of reading, ask questions about the slides. Pick a talking point on the slide and ask "do you ever deal with <insert point here> in your day to day?" It's a win-win for getting more information. If they say yes, then dig into it; if they say no, then you can respond "interesting, most folks I talk to in your shoes deal with that all the time. What does your day-to-day look like?" Worst case scenario, you get them talking and you learn something. 

This feeds right into my next point... not asking questions. I actually call this out on my demos before I even start presenting. I'll say something like: 

"my intention is to figure out whether or not my product is a fit for your environment. If it is, that's excellent; we'll figure out a package and I'll help you deploy it. If it's not, that's ok too; I wouldn't sell you anything you don't need. In order to keep my comments relevant to what's going on in your world, I like to have an open dialogue so feel free to ask me any questions you have and I'll do the same. Does that sound good?" 

If I don't get a verbal "yes" in one form or another, I will say "No problem. We have a huge library of videos on the website you can sift through and our marketing team runs a great webinar every Wednesday. My AE will reach out in a few weeks to check and see how that goes... if you like what you see we can try this again at a later date." and kick it back to sales.

This probably seems like a dick-move, but in actuality it's really not. If the prospect doesn't want to talk to me, having me pepper in questions and them feeling uncomfortable answering is an unproductive use of time. They will be much more engaged watching a non-interactive video than sitting there biting their fingernails hoping I won't talk at them. There's also a right and a wrong way to ask questions, which I will get to in a future post. 

The last piece is keeping your material fresh. This piece is different, because it's as much for you than it is for your prospect. Sure, they'll benefit from topical anecdotes and new feature release information about your product, but you will benefit arguably even more because you will draw energy from new content. This can be anything, to be honest. Maybe you inject a story about a previous call you had with a different prospect that will lay up a value-add for your product:

"I was just on a call with another guy earlier this week who was scanning all 8000 devices in his network BY HAND. "

 then try a question

"How big is your network? Does it take you that long to scan your devices?" 

Blogs are also a great place to get fresh material. If your company has a blog, grab a quote or an idea from one of the thought-leaders in your company and find an appropriate place to inject in your demo cadence. I have a plethora of blogs and news sites I check every morning to start my day with new hotness.

Lastly, on the other end of that phone is a person. Just TALK to them. Some of the best demos I've ever given were ones where I never shared a single slide. They're expecting to see your product, but the dirty little secret is there's probably lots of products that do what yours does. Customers don't buy products just because of the product, they buy the product because they like the people who are selling it to them. Don't be a demo donkey.

SE Fundamentals: The Need Behind the Need

This is one of those responsibilities that should be shared between sales and sales engineering... But is often not the case.

Apart from the who and the how (which should WITHOUT EXCEPTION be obtained by sales), the Why is the most important element of any deal. The why not only helps dictate the direction of the demo and POC/POV, but also gives us something tangible to fall back on later on in the deal cycle if it starts to go sideways. It reminds us why we think we can bill here, but also prospects of why they engaged with us in the first place.

The challenge with the why, is we all have a tendency to get generic with both the ask, and the description. In the security space, the need "we have to be more secure" is a great example of this. I can't tell you how many times I've asked an AE "so why did the prospect decide to join the call today?" And I hear some variant of "well, the prospect told me they need to be more secure and are always looking at security products". That's like a car dealership lot attendant coming to a sales guy and saying "there's a guy out there who wants to go faster and is always looking at new cars, I think we should talk to him!"

The reason finding the need is so important, is because time is so important. If a prospect isn't sure why they're looking for the product you're selling, they're probably not ready for a customized 1:1 demo. If this is the case they should be directed to your company website and/or YouTube page . Except for extenuating circumstances, an AE should NEVER schedule you on a call with a prospect unless they know WHY we're talking to them.

Unfortunately, this is not always the case. Oftentimes I get requests from AEs to hop on demos because "they have money, but I'm not sure why he agreed to see our product". In my book this is ok SOMETIMES... and ONLY if we have the who and the how. We can be nice, but I can't stress enough how this can NOT be the norm. If an AE preps me that they're unsure of the need, I will always agree to do the call and help them figure it out... unless I know they're making a habit of it and taking advantage of my good nature. Most often, I get a generic need that needs to be dug into one layer deeper.

So what is that next layer? For argument's sake, let's take the "we need to be more secure" proto-need. The first thing I'm going to ask is "why?" "Mr. Prospect I respect that, we all need to be more secure... So what's driving this sudden need to look at security products?" This should hopefully start to highlight something tangible that the prospect is trying to accomplish, but more often than not, the next response is "we're always looking at the latest technologies." To this I will most likely reply "well we definitely have the latest technology here, what current technologies are you leveraging? Do you think that's adequate? What other new and emerging technologies have you looked at? What element (or lack thereof) in your current security posture keeps you up at night? Did you see on Krebs the other day? This worried some of my other customers that they may have gaps in their infrastructure that could allow the same thing to happen, did you feel that way?" 

This line of questioning is aggressive, but because I don't have an actual need from the AE's disco call, it's going to tell me a few things. First, should I be on this call? Or... should they be watching a demo video on the website and the AE follow up in a week? If I deem the video is the best option, this is not a "fuck you junior AE I am above doing your worthless call", but more "let's see if the customer still wants a customized demo once they learn what the product actually does". This will also tell me whether or not I'm on the phone with the right person. The right person is most likely NOT someone who watches commercials for a living and has a free hour in his day, but someone who is invested in the outcome of the problem my product is looking to solve. Lastly, and probably most importantly, I am looking to educate the AE on the questions they should be asking before they engage myself or someone on my team for a call. During this line of questioning, the AE is most likely still on the call and listening in... And I'm always watching to make sure they're taking notes so the next time they're better prepared. 

I've always worked at startups and recently I've been doing some consulting for some companies that are at ground zero. Just hired a sales team, no formal training process, no predefined qualification requirements. In these cases, the LAST thing I want to do is insist. My AE's are ultimately the ones who are going to be building the customer base, therefore building the value of the business and making me money. If they're not adequately trained.. it is MY job to help. I can't stand asshole, entitled SEs that think every call should be handed to them on a sliver platter. The type of SE I'm looking for on my team is the real deal nose-to-the-grindstone SE that will suck it up and help the team figure it out. As SEs, sales training falls into our periphery so If you're too jaded with junior reps, go pound sand. 

Of course, if we're talking about a senior AE that should know better, I will throw them to the wolves every time. A proper sales bullpen has a pack mentality and if the SE respect factor is set up properly you can bet your ass the pack will eat the weak ones for breakfast... which is as it should be. As SEs we are an important element of the divining rod that tells which AEs will make it and which ones should try a different profession.