The toughest thing… no wait. One of the many tough things about moving from a technical role into sales is letting go of the keyboard. Accept that someone else will be doing the demo, and they have their own style and way of doing it.

I remember being on sales calls as the pre-sales person and having a "backseat driver" sales person with me: "show them that thing! show them the other thing! you missed a step!". By the end of one of those meetings I was about ready to bludgeon the sales person to death with my ThinkPad. In fact, I was present when a colleague did actually snap, and - in front of the prospective customer! - turned the laptop around to the sales person, crossed his arms, and said "you drive".

This tendency to want to stay involved with the technology is a symptom of a wider issue. Technical gigs, whether pre-sales, product management, technical marketing, professional services, or whatever, are more similar to each other than any of them are to sales. I have seen people fumble that transition, getting bogged down in technical details that are no longer their job. This doesn’t work for anyone.

Part of it is also the cultural divide between tech and sales¹; it’s a big change in self-image to start to see yourself as sales, and there is a tendency to want to prove that you’ve "still got it".

Why is it that no matter what it says on my business card, I still end up messing with regexps on a semi-regular basis?

— Dominic 🇪🇺🇺🇦🏳️‍🌈 (@dwellington) March 9, 2016

It’s tough to accept, but you have to let the tech team handle the tech issues; that is no longer your job. Meanwhile, they are relying on you, the sales person, to cover the sales stuff: is the deal qualified, have we met the economic buyer, do we understand the business case, what are the deadlines, and where are the pitfalls?

This is not to say that you should ignore technical details. Make sure you are current on what is a unique versus comparative differentiator, and how that landscape changes as both your own product and competitors evolve. It’s just that you are no longer using that information in the same way as you were when you were in a technical role.

This is as much a reminder to myself as anything else: give your technical colleagues feedback and inputs, but you have to let them do their job, which is no longer your job. It’s a sales team, and everyone has to play their own position.

Let’s see, the mother company just launched a hot new product and customers are emailing about it. I think we should ignore them and focus on pushing mediocre products on drive-by prospects.

If you tried this in any other industry, you’d be fired with extreme prejudice. But in car sales, this sort of thing seems to be standard operating procedure.

There was the time I almost had to rugby-tackle a salesperson in the showroom to get them to pay attention to me.

There was the time when, still pre-kids, I was looking at two-seater sports cars, and chased the dealership for six months (!) to get a test drive. Finally instead of just arranging a test drive, they comped me a full day of driving academy on the Monza F1 circuit, which they told me was several thousand Euros’ worth. This day gave me the chance to do several hot laps in the BMW Z4 M Coupe, plus messing around in a Mini Cooper S, a 135i, and a 330d M Sport, on the skid pan, in the cones, and generally left me with a huge grin on my face.

Think they followed up with me afterwards?¹

The current idiocy is over the new Abarth 124 Spider. The announcement made quite the splash, and I am thinking vaguely about a weekend car, so I messed around with the configurator on the Abarth site (not that you can do much with the spec), and then filled in the form to be put in touch with my local Abarth dealer.

Crickets.

Tumbleweed.

Okay, fair enough, they probably get a number of time-wasters wanting to drive their hot cars, and I’ll be the first to admit that my interest is tentative and not immediate. Still, it’s the twenty-first century. You can at least set up an auto-responder - "thank you for your interest", sort of thing.

I have already written off ever owning another BMW because of shenanigans my local dealer pulled - not just on the sales front, but in maintenance. Their shoddy workmanship left me by the side of the road and forced me to cancel a very important meeting, but the worst of it was that they refused to apologise when I called them on it.

Customers are fickle, but not that fickle. Treat them right, they can be yours for life. Treat them poorly, you’ve lost them forever.

The part of the process of engagement that makes the greatest difference is the point of contact with the customer. I love BMW products, regard their advertising as high-quality, and generally appreciate the company in every way - but I will not have anything to do with the local dealer. The process of terminating my Fastweb contract was so unpleasant that despite the fact that I had been a fan until then, I will not only no longer consider them for myself, I will go out of my way to advise others to avoid them.

The local VW/Porsche dealer, on the other hand, treated both my wife and me so well that I can see myself sticking to VAG products for the foreseeable future. Same goes for Vodafone: even when they have had technical difficulties, they have been so communicative and willing to engage that I have made allowances, and still recommend Vodafone over alternatives.

I try to do the same in my own sales engagements. I do my best to communicate in a clear and timely manner, and so far, it seems to work. My end of the IT market is of course a pretty small shop, so I am strongly conditioned to treat people well because I keep running into the same people over and over. Even in mass markets, though, people talk, and through social media, your actions will catch up with you.

As the saying goes, you only get one chance to make a first impression. Make it count, whether you’re selling cars, phone lines, or enterprise software.

Young people these days, am I right?

We have fallen upon evil times,

And the world has waxed very old and wicked.

Politics are very corrupt.

Children are no longer respectful to their parents.

Author: Naram Sin, King of Chaldea. Date: 3800 B.C.¹

I don’t know how long is too long to be in sales, but I have now been doing it for long enough that I can look down at young whippersnappers and their naivety.

Today’s example is actually a perfect storm of sorts, involving Silicon Valley VCs, a Bitcoin startup, and large enterprise processes. I was listening to the a16z podcast, which as usual is about equally irritating and enlightening. The guest on this particular episode was one Adam Ludwin, whose claim to fame is as the founder of a Bitcoin - sorry, blockchain startup, called Chain.

I find the techno-utopianism of everything associated with Bitcoin to be jarring at the best of times, but Ludwin and Chain have an interesting angle on it. Instead of enabling drug dealers and software extortionists, they are trying to enable large financial institutions to carry out their business using the blockchain, instead of the weird semi-analogue hodgepodge of processes that banks run on today.

I’m not going to get too deeply into what Chain are up to - if you want to find out about that, you can go listen to the episode. What I found jarring was his surprise at what he found when selling into those large financial institutions. Anyone who has spent time selling into large enterprises could have told him this, but apparently he had to learn it the hard way.

For the benefit of everyone else, here are a couple of key points.

Executive Sponsorship

Nothing gets done without buy-in from the CEO. (direct link to relevant quote in podcast)

NO REALLY STOP THE PRESSES HOLD THE FRONT PAGE

Let’s get real: moving anything that is currently working to unproven technology such as the blockchain is going to require strong executive sponsorship. This is not unique to the financial industry, either. Whenever there is an existing process in place that works, however creakily, there is resistance to any proposed solution.

There is nothing inherently wrong with this resistance: the existing process has been refined over time and is well understood, including its failure modes. The proposed new solution, however, is by definition unproven, and will almost certainly require a period of acclimatisation before it becomes as reliable as what went before, let along delivering additional value.

Graphic stolen from Ben Evans

The people who are least likely to see the problem with the way things have always been done are the people who are in charge of that existing process. They are trapped on a local maximum, and while they may accept the theoretical existence of higher maxima elsewhere, to reach them they would have to cross a valley of lower service, lower user satisfaction, possibly lower bonuses, and even perhaps place their jobs at risk.

This is why the most fearsome competitor that you face when pitching anything transformative is not That Other Company, but the Do-Nothing Corporation. You need a very good answer to the question "why do anything?" before you can even get to "why do this?", "why now?", and eventually, "why do it with this company?".

People in upper management, on the other hand, are there specifically to take a strategic view, accepting tactical defeats in the name of the ultimate strategic victory. If you want to change anything that is required for a company to operate, you will need strong executive sponsorship: someone who not only knows the current state, but understands why it cannot continue, and is willing to engage with you to investigate alternatives.

What is tricky for many people just getting into enterprise sales is that the initial pattern often looks the same with and without sponsorship: an evaluation, a proof of concept, a pilot project, or an engagement with the innovation lab. There will be meetings with architects, CTOs, requests for this and that, strategy sessions, deep dives, and workshops.

The key point, though, is that precisely none of this frenzied activity will actually lead to a deal and a production implementation without that executive sponsorship. Green sales people can waste a lot of time and resources going through these motions and not achieve any results because they missed that all-important first step.

On the other hand, once you have a sponsor who can make things happen for you, the evaluation will go that much more smoothly. Partly this is because you can call on your executive sponsor to sort out the inevitable brown M&Ms sorts of problems, but mostly it is because they will clarify what is an actual business requirement versus technical curiosity or "nice to have" feature.

So far so good, right? Well, if it were that simple, everyone would be doing it. The other issue is that it can be difficult to find anyone that has visibility into the whole process - which is the other point I want to discuss.

Distributed Knowledge

"At any given institution, it’s very very rare to find someone who actually knows how the whole thing works." (direct link to relevant quote in podcast)

This is something else that people don’t always get when they begin dealing with large organisations. Very few people have visibility into the whole problem². Here is an example from my own past:

Years ago, I was the tech guy on a team selling to a mobile telco. As part of our business case, we were trying to quantify the impact of downtime on a system that activated SIM cards. We had some numbers from IT, but they were incomplete. We rounded them out with some numbers from the helpdesk, but we kept feeling we were missing something. Finally, the sales guy stopped off at a couple of corner shops that sold the SIM cards, and found that the impact was far greater than anyone imagined. It turned out that the shops rarely activated the SIM cards with the customer in the shop, but did them all in a batch at closing time. This created the overload spikes which were taking the central system down, but it also meant that the downtime was costing far more than anyone imagined.

In that situation, when we asked the IT team, they described the part of the problem that they saw. Actually, it was more complex than that; we had to speak to a number of dedicated teams within IT, from servers, to databases, to middleware, to networks - but at least we were able to find people within IT who did have visibility across the IT parts of the problem. The main point, though, is that as far as IT was concerned, everything was fine. The parts that they saw were doing fine, all of their indicators were in the green except for a couple, and they believed themselves to be on track to address those.

Support had an idea that something was wrong, but it was only at certain times, and at other times everything was fine, so the problem seemed to be contained.

Meanwhile, in the corner shops, customers were getting frustrated and picking up the competitors’ SIM cards instead, because they could actually activate those and use them to make phone calls.

It turned out that literally nobody within the company understood the entire end-to-end process. This was a core business process: we were dealing with a mobile telco, and the process we were analysing was the activation of new subscriber SIM cards. One of the key metrics that the company measured itself against was churn, the difference between customers acquired versus those lost to their competition - so customer acquisition was a critical step, and yet nobody truly understood the entire process of how new customers were acquired.

What I learned is that this is normal. The sorts of processes that modern business runs on are too complex to be understood in their entirety - not when there are a hundred and one other tasks demanding people’s attention. When selling to these organisations, we need to ensure that we understand what we are proposing that they replace - and this means talking to many different people, because nobody sees the whole picture.

People working inside complex processes are busy with individual trees, and not necessarily focusing on the entire forest. Vice versa, if we are to propose that foresters change how they manage their trees, we had better have a pretty comprehensive picture of why.

Anyway, if you are a brash startup planning to sell into large corporations, just be aware that there is a lot going on inside those buildings - and much of it even makes sense, if you take the time to understand it. Selling to enterprise is different from selling to consumers or SMB, and needs to be approached with different tools.

Image by Jakub Sejkora via Unsplash

I've spent most of my career around enterprise IT sales. I have learned a lot from my colleagues on the sales side, which makes me much more effective in supporting them. After all, let's not forget - whatever your business card or your email sig say your particular role is, ultimately we're all in sales, or we're all out of a job.

One of the things I have learned, however, is that there is a very common misunderstanding of the role of marketing and advertising in enterprise IT sales.

The first thing to bear in mind is the difference between direct marketing and brand marketing. To quote Wikipedia,

Direct marketing is attractive to many marketers because its positive results can be measured directly. For example, if a marketer sends out 1,000 solicitations by mail and 100 respond to the promotion, the marketer can say with confidence that campaign led directly to 10% direct responses. This metric is known as the 'response rate,' and it is one of many clearly quantifiable success metrics employed by direct marketers. In contrast, general advertising uses indirect measurements, such as awareness or engagement, since there is no direct response from a consumer.

Measurement of results is a fundamental element in successful direct marketing. The Internet has made it easier for marketing managers to measure the results of a campaign. This is often achieved by using a specific website landing page directly relating to the promotional material. A call to action will ask the customer to visit the landing page, and the effectiveness of the campaign can be measured by taking the number of promotional messages distributed and dividing it into the number of responses. Another way to measure the results is to compare the projected sales or generated leads for a given term with the actual sales or leads after a direct advertising campaign.

Sales people tend to assume that all marketing should be direct marketing - that is, marketing that should trigger a measurable action. Each campaign must generate a certain number of leads, a certain percentage of which will turn into actual qualified opportunities, and with any luck some of those opportunities will eventually close.

Coffee is for closers only

Of course this situation generates all sorts of fun conversations where sales people question the quality of those leads, while marketing answers back with barbed retorts about the number of opportunities that the sales team actually convert. Lost in the Sturm und Drang of the resulting blamestorm is the question of whether this model can even work at all.

On the other hand, straightforward brand advertising is ridiculed as a waste of money. Since it is hard to measure almost by definition, it doesn't fit into the usual opportunity conversion spreadsheets, and is therefore the first expense to be cut when Sales is driving the bus. In fact, the only way of measuring the impact of brand advertising is by looking at what happens when you stop doing it.

I would argue that for the sort of long-duration, big-ticket sales cycles that we have in enterprise IT, the expectations of direct marketing in the traditional sense are overinflated. On the other hand, the potential of brand advertising is vastly underestimated - including by marketing departments.

Brand advertising - what is it good for?

Very few people in this space will make or even consider a purchase based on a single campaign or targeted VITO letter, no matter how good. This idea plays into the heroic self-image of sales, but it is rarely true. In actual fact, before receiving that first formal sales approach, our prospect already has an opinion of what our company and products are like. This opinion is formed from various different sources, but the most important ones are personal experience and received opinion. If you can get personal experience right the first time you have generally bought yourself a customer for life, but that's a whole other topic. The way you can influence the frame of mind of your VITO is to work on that other axis: the received opinion that they already have of your product and/or company.

In turn, that received opinion is also determined by two main sources: word of mouth, and - yes - brand advertising. Brand advertising helps position your company as the sort of company that your VITO would want to do business with: innovative, customer-focused, stable & reliable, or whatever your particular values might be.

A prospect reading a VITO letter

So far, so much like direct marketing, except without the all-important metrics. Where brand advertising pays off is in what happens next. What you want to happen after VITO reads their customised¹ letter is that they run down the hallway, burst into their colleague's office or their team's open space, and announce excitedly that they have just read about a very cool-sounding product from your company.

Their willingness to do this - to expose themselves in this way - is going to be predicated on your company's credibility in the space where you operate. In 2015, anyone getting excited about a new offering from Blackberry would have to do a fair amount of explaining (sorry, Blackberry). Vice versa, nobody has to explain why they are planning to buy cloud services from Amazon, storage from EMC, networking gear from Cisco, or insert your own favoured example.

While no amount of brand advertising could save Blackberry at this point, Amazon, EMC, Cisco, et al got to where they are in no small part by working on their perception in the market. In other words, their brand advertising ensures that VITO will be excited, rather than embarrassed, to involve their colleagues in an evaluation and advocate for a new offering.

What advertising can and cannot do

None of this is to say that brand advertising alone is sufficient if the products themselves don't meet expectations around price, performance, support, or any other axis that is important to customers. However, brand advertising can help get to the point where those variables can come into play.

Ironically, this distrust of advertising is one of the very few things that sales people and engineers both agree on. Both are making a category error which is nicely explained in this episode of the excellent Exponent podcast, with Ben Thompson and James Allworth.

Bottom line, I think overlooking brand advertising is a false economy. If you’re a startup, of course, you can’t blanket airports and fill out business magazines like the big guys², so figure out what you can do in that space. And if you are big company that doesn’t do brand advertising, know that prospects are asking themselves why that is - and this definitely feeds into the perception they have of your company.

I have a liking for terrible puns, so I have always had a soft spot for the analyst firm Horses for Sources. Their latest newsletter included a link to a blog post which I'd meant to write up the first time around, but got distracted… ooh! A squirrel!

Ahem. Anyway.

Here's the piece: Time to stop the buzzword balderdash and become meaningful again.

Am I smoking something illegal, or has our industry really started to lose the plot with the amount of buzz terms that – quite frankly – only mean something to the sellers and advisors trying to make their wares sound that little bit savvier than their competitors. And even then, I am not too sure whether many of them even fully understand what they are buzzing about either, more simply regurgitating what their competitors are saying.

They also provide a table of examples, which really doesn't look good for anyone talking about SMAC¹:

I don't think the problem is with people parroting their competitors. Rather, in each company the "thought leaders" come up with terms like DevOps, cloud, or, yes, SMAC, and they mean something specific by them. Over a period of time when they are hashing out their concept, they develop these sorts of verbal shorthand to refer to quite complex structures.

When these deep thinkers are communicating the concept to outsiders, sometimes – often – they forget to provide the extended definition and associated context. Their audience of sales people and other front-liners half-understand the concept, learn the shorthand by heart, and end up in front of customers regurgitating poorly understood messages. The result is basically cargo-cult marketing.

The problem is not that the various visionaries have their own jargon, or even that they talk in acronyms. The problems begin when they come down from the mountain and forget to translate that jargon into common language. The point is not to sound smart to people who don't understand the concept, but to communicate that concept.

A theory that you can't explain to a bartender is probably no damn good.
--Ernest Rutherford

Surprising! Least valuable interaction during buying cycle is with Sales #GartnerResearch on CustomerInsights. Tiffani_Bova #IMCloud 2014

— HPE Developer Community (@HPE_Developer) April 9, 2014

Why is that surprising? There are other people on the team with the actual knowledge that customers are after. It is unfortunately only exceptional sales people who add much value to the sales process - as opposed to just moving it along.