Sean's Musings as a Service

Sean's Musings as a Service

Selling horses and pork

  • Published:
  • categories: sales
  • tags: selling, politics, corporate, leadership

Less technical post today, I have changed jobs over the past few months and it has given me some time to work in a new role where I am much more the master and commander of my time, my engagements, and the outcomes of effort. Not that IBM was not able to do this, but the bureaucracy was a heavy burden to work through.

Eye opener

Came back to the US with a new appreciation for global work and the challenges of working in software sales. It was eye opening to experience how the sausage is actually made, and not necessarily in a good way. I went into the experience, like any good little developer would, expecting that software selling really about showing technical capabilities, demos, and winning business based on merit and function. However the honeymoon was quickly over when I found out that this is so rarely the case, the most important thing in closing a large “HP/Oracle/IBM/Microsoft” style software deals is the relationship between the seller or sales team and the champion in the company. So it was truly dis-heartening for the first 6+ months to go into accounts using or mis-using terrible software and unable to get traction strictly based on politics, weak relationships, and generally just seeing clients suffer for poor decisions not based on sound logic.

Not that what I was selling was always the best, and yes I saw the opposite side of this where I benefited from absence of common sense from the software purchase and deployment.

It is getting better, slowly

To a certain extent this is getting better in at least two ways, one positive and one that is at best neutral. The first one that is good, there are more highly skilled people in senior leadership ( VP, P, C*) level positions that truly understand technology and how this does or can be used to drive a more efficient set of core business systems. The second the current set of IT managers and VP, P, C*’s that do not understand this new world are aging out of the workforce, this is more so true of some of the more old school companies today but I am constantly surprised out how companies are actually run. I’m not being age-ist, this is a skill gap not a generational problem, the IT industry in general suffers from weak leadership in the middle management space, far too many people have been promoted from the job they did to lead a team of people doing the job without have the corresponding people management and/or leadership skills to actually run teams or teams of teams.

Is there a better way?

Of course, we can always do better, regardless of what some people want to limit themselves to. Change is hard, but change is necessary, failure to implement adaptive IT is probably the number one killer of most of todays large corporations. Technical debt like financial debt can only be allowed to get so high before it stops the company from being viable.

The way forward is to accept that things are not where they should be today. In the ideal scenario, your company identifies a business opportunity a new insurance product, debit card, rewards program, et cetera… you design, implement, and release it. The most successful companies are doing these types of cycles in hours and days. Clearly there are risk factors to constant change so this is not applicable or desirable everywhere. So based on the fact that other large corporations are able to make changes like this, it is safe to assume that this is possible regardless of what you may want to believe or have been told.


While this is overall a pretty negative spin on the IT Software Sales industry the good news is that the disruption of startups and genera SaaS availability to many offerings has caused wide-spread disruption to traditional large Software Vendors ability to continue to operate a monopoly. While these dinosaurs evolve or die out the landscape of the industry will continue to change to where I see companies much less interested in buying from a single vendor but much more likely to pick best of breed per requirement and leaving the IT teams to figure it out, but that is a problem for another day.