Shopify on the Slow and Steady Train to Enterprise

I often get asked if Shopify is making progress in Enterprises. The answer is of course yes, but often you can't see the progress beneath the surface. You only see it when the train comes out the other end of the tunnel.

Primarily the installations heading in the Shopify direction in Enterprise are vintage 2010-2014. Many are some level of hybrid-custom system, but many are some flavor of Demandware (depending on the vintage year - often SFRA pipelines or controllers), frustrated by the huge Salesforce bills that seem to be getting ever higher for a stack which is increasingly harder to maintain for something not improving at the same rate.

Still, Enterprise Sales takes time. You need credibility, convincing, comfort, and patience. Shopify has the "earned media" power that most platforms would envy. That might start a conversation that ends up going nowhere.

These deals need to pass a lot of hurdles for Shopify to even have a chance at bat:

* Investor event, platform EOL support, or contract coming up.

* Digital Organization comfortable with SaaS/Shopify (usually it starts here in traditional IT organizations - often the business teams come from other places)

* An IT organization stretched thin and beaten down, or a retiring IT leader.

Even then, you still need pass what I call the "arc of skepticism" with the IT organization through a progressive series of meetings over a 6 month to a year period:

1 * "Shopify is a toy."

2 * "Maybe we should take another look, but do we really want a new vendor in the mix?"

3 * "It does seem to be more flexible than we thought before."

4 * "OK maybe we admit there could be some advantages here."

5 * "We might even look like heroes."

Somewhere in between steps 4 and 5 the CEO and CFO get together and step in. The traditional Shopify story of TCO and Innovation is great for the mid-market but in Enterprise IT settings, it is often not enough only for the Business teams to keep trying to push the rock (Shopify) up the hill (IT) like Sisyphus.

Whether this arc of skepticism takes 3 months or 3 years depends on how rigid the IT organization is, the requirements of the business and IT, how large the company is, privacy/data/security audits needed, and sometimes whether or not the old IT leader is on the way out or not.

Even then, a successful sale might lead to an implementation disussion that can be an interminable nightmare of delays, sequencing, budgeting. Shopify can solve the platform, but the integration problem is another story altogether. Integrating Shopify with a complex Enterprise is its own beast of an operation, and the primary reason that these implementations might delay or some may not ever even see the light of day.

This is what Shopify has signed up for and I see many in some stage of this "arc of skepticism" and others in the "interminable implementation" stage. Of course some are live too 😀