In my conversations I've observed three segments of enterprise retail organizations today, as it pertains to their digitial and technology initiatives.

1 - Companies with bad CTOs

* Try to deflect new investment projects

* Defensive

* Are trying to expand their empire and own the list of projects.

* Difficult to collaborate with

* Always trying to consolidate vendors, almost as if they are acting as an extension of the Procurement Team

* Often these organizations have a non-technical or disengaged CEO.

Even if the business tries to transform, they have no technology partner to make it happen.

Basically you have an old-school IT organization.

In no way are these organizations a fit for headless. Even if you can implement it, it will stop serving the business needs the second it launches.

2 - Companies with great CTOs but no Chief Digital Officer

* Open but limited bandwidth and buy-in can limit their effectiveness.

* Trying modern approaches

* Innovating in pockets, but not across the board: don't try to overcommit

* Difficulty getting the business on-board and even in the room to

transform the organization.

* Difficulty communicating the business value of their deliverables

* May not fully recognize their business partners in other organizations (marketing, sales, supply chain, etc) can be just as innovative, but there is no one to bridge the gap between the two.

* Sometimes I have seen a product management organization under here. Even if they are in the wrong place, it can be a good sign if the right team is there.

This group is trying to transform, but have no business partner to make it happen. Headless might be a bridge too far until the business can be brought along.

3 - Companies with great Chief Digital Officers

* Aligned to the goals of the CEO and Board of Directors

* Innovating to move metrics important to the brand/customer experience, revenue and profit.

* Much easier to get buy-in to new initiatives and communicate the value of transformational initiatives

* Bridges the gap between the rest of the business and technology

* I have seen some organizations that put technology in this organization, and some separate it out.

* Usually a great Data organization can reside here. In a huge enough organization, that can be split out too.

* Will have the easiest time moving to a headless solution