Strategic Sales and Spycraft

A friend recently asked how a sales person might move into a domain where compensation might be expected to exceed USD$200k a year, with 5% commission.

That’s the domain of enterprise sales, and related large-scale sales endeavors.

Any large organization, indeed: any large dollar purchase, will be authorized by someone that is referred to as the “decision maker,” and it’s extremely unlikely that you’ll ever meet them, or even know who they are.

The methodology in the business world for navigating this labyrinth is generally referred to as “strategic sales,” and there are many formal educational frameworks that teach how to do this, but all are similar in that they encourage interrogative discovery to map the decision-maker and its exclusive ecosystem of influencers.

The annoying thing about enterprise and strategic sales is that nearly every sales person is convinced that they are speaking with the decisionmaker, but if you’ve not received a check, you’re not speaking to the decisionmaker; a very simple performance indicator.

Indeed, the influencers who describe themselves as critical to the decision will often milk people for their time and information so they themselves might curry more favor and influence from the decision maker.

So in the context of enterprise or strategic sales, you’ll get a salesperson who will claim that they’ve been speaking with the decision-maker for a large-dollar sale…for two years.

But again: if a check has not been written, you’re not talking to the decisionmaker, you’re talking to an elaborately-constructed gatekeeper who themselves is granted a certain elevated position within the ecosystem in exchange for their ability to milk people (and their ego for) information, without any compensation.

In fact, I just described to you the dynamics behind tradecraft, defined as:

Tradecraft, within the intelligence community, refers to the techniques, methods and technologies used in modern espionage and generally, as part of the activity of intelligence assessment. This includes general topics or techniques, or the specific techniques of a nation or organization.

More commonly referred to as spycraft.

People think there’s a scarcity of money, but that’s false; there’s lots of money, it’s just being allocated elsewhere, and your trick as a strategic sales person is to persuade the “black box” ecosystem (and therefore the decisionmaker) that an investment in your product or services is more valuable and important than what is currently allocated.

And again: unless you’re doing retail sales, and if you’re truly in the domain of strategic sales, it’s not likely you’ll ever know who the actual decision-maker is.

Indeed, the people you’ll speak with need to be persuaded to advocate on your behalf, and from a place of convincing authenticity, which means that they will need to take your ideas and present them as if they were their own.

Which begins to resemble the domain of consultative sales.

Consultative sales is a specific sales approach where reps act more like advisers than salespeople and recommend solutions to potential customers based on their needs and problems. Put more concisely, it’s the process of selling a solution, not a product.

In other words: it’s an application from the domain of education, albeit one where great educators are highly-compensated.

To that end, your “students” within a large organization typically make safe choices, not correct ones, which again is a function of people‘s lack of faith and risk aversion.

The larger the opportunity, the more risk-adverse the ecosystem surrounding the money which might be provided to secure the requisite goods and services.

In business theory, disruptive innovation is innovation that creates a new market and value network or enters at the bottom of an existing market and eventually displaces established market-leading firms, products, and alliances.

When you study the literature on the use of disruptive innovation, you’ll see that ironically, large organizations are actually financially compensated to find and suppress disruptive and correct innovations, because they are actually just risk-adverse gatekeepers who believe themselves to be responsible for large decisions.

The higher within a hierarchy you travel, the more authentically these gatekeepers can persuade others that they are interested in disruptive innovation, but again, if they’ve not signed a big check, they are not likely the decision-makers.

Within cities, one important decision-maker is the city manager, which translates to the chief financial officer within private enterprise, whose primary consideration is the preservation of corporate assets.

The character “Ron Swanson,” from the television show Parks and Recreation is an expertly-created example of a city manager, as well as a chief financial officer from within private enterprise

In my career I’ve worked with some truly-great strategic sales people, and they have a sense of humility in the sense that they never truly believe that they are actually speaking with the decision-maker.

These people never rest on their laurels, and they are not inclined to believe that their message is “landing” within the target organization, not until that large-dollar check has cleared the bank.

This sense of humility keeps them on their toes, and their mind cycles endlessly as they explore the black box until they find the person who has the wherewithal to just write a check.

Of course, it’s likewise possible that the message itself is insufficiently tuned to penetrate the elevated tiers of a large organization; great strategic sales people have negotiated a seat at the table of those responsible for positioning, product/service capability (normally: marketing and product management).

The point is: the emphasis of their daily creativity is upon the continued illumination of the black box and its ecosystem more than their proposed solution.

The theory of constraints is a management paradigm that views any manageable system as being limited in achieving more of its goals by a very small number of constraints.

From the domain of manufacturing came the theory of constraints, which suggests a methodology whereas one:

  1. submit all resources to its alleviation
  2. lather, rinse, and repeat

The bummer about strategic sales organizations is that they are almost entirely made up of people who are easily bamboozled by important titles of people in their list of contacts without the more humbling acknowledgment that none of those people have paid them very much money, and have mostly drained the sales person of valuable time.

Because again: these well-positioned gatekeepers are trying to milk information, so they can both protect the organization from risk and create more favor from the actual decision-makers.

Of course this is a pretty cynical point of view, suggesting that there’s winners and losers.

It’s more realistic to acknowledge that these “gate-keepers” are actually trying to elevate their influence within this same ecosystem, and so herein lies a great educational opportunity, which brings us back to the consultative sale, mentioned earlier.

A great strategic salesperson is one that positions themselves both humbly and assertively in such a way that they are fancied indispensable to a targeted ecosystem of influencers, so that they might orchestrate a compensated series of organizational changes in exchange for a series of large-dollar investments.

You can perhaps see why great strategic sales people are hard to find; ego is a massive trap. And so it is in the domain of tradecraft (spycraft).

The industry is filled with enterprise sales people who create massive volumes of correspondence, and from their perspective it’s basically a numbers game, a sales funnel worthy opening is vast in size, but diminishing to a very small straw.

I’ve created educational programs for strategic sales organizations, because I’m pretty decent at this methodology, (because I’m a decently skilled hacker), and because I have a knack for spycraft.

And salespeople in general are tricky because they have a lot of ego about how important they are, how they have all of these decision makers in their Rolodex.

So in the context of enterprise sales, I have to actually demonstrate to the salesperson (as an unwilling student, in this context) that I’m better at it than they are, and of course they resist it … until I help them land big sales.

Proof’s in the pudding, y’all.

If you look at the recommendations on my LinkedIn profile, you can see that there are lots of extremely successful enterprise sales people (and former customers) who think I’m the cats meow; it’s because I help them make their numbers.

If I’m behind a certain endeavor, I know how to navigate that labyrinth without much effort.

For what it’s worth, I hate the hustle of trying to land a big sale, and I find the effort a waste of time, actually it’s insulting to me on a personal level, because I simply refuse to kiss up to the kind of inauthentic aspiring influencers who have not the humility to present themselves properly vis a vis an actual decision maker, and corporate and municipal environments are filthy with these folks.

I’m not notoriously patient, is what I’m saying, and some issues (such as the domain of security) are egregiously in need of help, unfortunately hindered due to conflicts of interest within the culture itself.

This is actually what led me to study the relationship between political science, economics, and law, because I consider them three complementary sides of a prism which deobfuscate the blackbox in an efficient manner.

When aspiring to deliver a large impact upon a targeted ecoystem, I find it more effective to steer the large organization towards a particular outcome, by orchestrating various episodes both outside and inside the risk-adverse organism.

That’s literally what I’m doing right now with 214 Alpha, by the way, which follows a lot of experimentation I did a generation ago regarding skateboard park activism, itself in elaboration upon certain experimentation I had done 10–15 years prior with the Burnside Skatepark success, itself building upon years of failure and experimentation.

In general, large cities were not able to cross a certain risk-averse threshold (I would suggest a ratio serve as a KPI) until a number of smaller municipalities in the same region had likewise crossed their own risk-averse threshold (lower for smaller organizations).

In Oregon, the ratio was about 50 to 1, small cities to Portland.

When the city of Portland approved our plan for a skate park system of 19 parks, it had only occurred because we had delivered about 50 smaller skate parks in the region, and look: the mayor at the time, former chief of police Bud Clark, his brother was my grandfathers administrative assistant, when my grandpa was the personal director for Burlington Northern.

Point being: even though we were well-connected from a place of privilege, it still took that much effort and that many years to make a difference, from the outside in, and from the inside out.

Here in central Texas the ratio proved closer to 40 to 1, meaning about 40 adjacent communities had to cross a certain risk-averse threshold before the city of Austin proper did anything of substance, and again that was because we used the hell out of our connections and privilege, from the bottom up, from the outside in, and from the inside out.

And you’ll note that the methodology used was one that positioned our activists as servant leaders, and subject matter experts, on-hand to assist organizational “influencers” to succeed within their own endeavors.

John Keats would appreciate this lovely quote, which is ironically placed in concrete on the streets of Portland, Oregon

My point: for our large-scale endeavors, a majority of our efforts were invested outside the targeted large organization, which because the actual influencers and the actual decision-makers weren’t in the city organization, proper.

That’s frustrating for many, and it’s easy to talk trash about large organizations, but their risk aversion is a function of their investment in continuity.

There are plenty of reasons why a large organization will resist risk-taking exercises which could render its current models obsolete.

They are slow moving on purpose, because they are the organizational equivalent to a battleship that can leave craters the size of tennis courts, lobbing projectiles from behind the horizon….but are slow-moving and boast their own inherent vulnerabilities up close and from within.

So when I map influence networks, influencers, decision makers, and use other methodologies, I frequently find that large organizations are often limited in the manner by which they are ultimately subject to the whims of decision makers that are technically outside the ecosystem.

For instance. A few years ago the city of Tacoma was pressured into doubling down on its restrictive policies regarding skateboarding, and I could tell that they were prepared to receive the anger of outraged skateboarders.

Indeed, our activists quietly went to the business community, and not everyone, just the ones that mattered, and this was the pitch:

Slide 1: Cities have criminalized skateboarding since the administration of Jimmy Carter, and this policy has failed.

Slide 2: The cities failure to provide a recreational outlet has pushed recreation into the lapse of business owners, whose role within society is to provide jobs and opportunities

Slide 3: it’s our recommendation that the city excepts recreational responsibility in the following precise, low cost manner, with these associated low cost maintenance outcomes.

Of course, this outline was concurrently leaked to just the right parties inside the organization, and guess what?

The city caved, literally capitulated from the office of the deputy mayor, because the actual constituents of city policy, the actual decision makers were in the business community, and they understood the calculus when it was presented in a form that they could easily understand, using language that was accessible to them.

This is exactly true within enterprises; yet another large organization.

Bank of America has a few dozen vice presidents of corporate and information security, and organizationally, linguistically, even legally as well as economically they are described as “decision makers.”

Indeed that’s not true. Not for large purchases that are truly important.

They are subordinate to decisionmakers that are not technically part of the Bank of America ecosystem at all.

A great enterprise or strategic sales person is one that’s able to discern and map these influence networks as they transcend the target organization, and they demonstrate wisdom when they make a decision about whether or not it’s worth their time to go down that rabbit hole, or to influence outcomes from elsewhere.

In terms of personal temperament, I would rather focus on the opportunity domain that they explicitly overlook, which is down in the trenches, what are dismissed as low dollar deals and none of their interest, but in the aggregate is what actually makes a battleship move.


When my grandma died my grandpa bought a pretty big boat with twin Volvo engines, and if you looked at its specifications it was a fairly impressive vehicle.

But the Columbia river? It’s one of the largest rivers in the world, and as it intersected with the Pacific Ocean, the water didn’t afford the will of the boat’s pilot much weighty consideration.

Listen: when Mount St. Helens exploded, in 1980, an entire forest was blasted into splinters, and the floating wreckage of that event clogged a river that is almost five miles wide from shore to shore.

And yet even the river, which has flowed with great irresistible will, shrugged the whole thing off, and merely passed the forest into the arms of the Pacific Ocean, even as the flotsam battered and bruised a small fleet of trapped ocean vessels.

And so as a pilot of my grandfather’s boat, one could really lean into those twin Volvo engines, and one could turn the rudder, but at best the pilot was issuing requests from a watery “DJ” that had its own playlist in mind, so to speak.

The truly great strategic sales people are the ones who understand their own limitations from a place of intuition and humility, and when they are able to successfully effect change through the education influencers from within, and from without, they receive compensation at least as high as what my friend described as an aspirational level (USD $200k w 5% commission), but frequently much higher.

Allow me to suggest that money (both hard and soft capital) serves as an allegory for a “social pheromone” that betrays the values of a particular culture or organization.

A truly great strategic sales person is more like a sociologist, an anthropologist, and ethnographer, as well as a subtle zen-like teacher that knows how to read the audience, knowing that if they are truly successful in their endeavors, they will likely be forgotten, because they will have persuaded the target audience to make a decision as if it were their own.

Hailing back to the domain of consultative sales.

Again, at this level it’s nearly indistinguishable from spy craft, and as with the domain of spycraft, ego is a major inhibition to greatness.



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Kent Dahlgren

Product management fix-it guy. World-famous people skills. Extremely small hands. (edit) marketing lady says I’m also supposed to say “CEO of software company”