Hi Anushree
Thanks for the questions. These are questions that I’ve spent a lot of time reflecting and thinking about over the years 
I’ll answer a couple and come back to the rest.
- Not only did we jump into retail as complete retail noobs, we also jumped into enterprise with no background there either. Feels like a double whammy in retrospect. To be honest though, we were blind to both and it might sound weird - but it was a good thing in a way because we definitely lacked the fear we now feel, as people who know so much more about this industry than when we started.
We did 3 things really well:
One, we knocked on a lot of doors and spoke to a lot of retailers who were willing to talk to us. We had a hunch about a set of use cases in personalization that our Computer Vision stack lent itself really well to. So we built a bunch of demos and took it around and did a lot of show & tell but more importantly, used it as a simple starting point for conversations around problems retailers had. We were way ahead of the market (I don’t say that in a good way) and that meant people often got excited and gave a lot of feedback and ideas but never really followed through. We were able to get people to open up their systems, stack and show us what they had going. Lesser the pressure to buy, the more the intent to share, sometimes, especially in cases where your category is non-existent but exciting.
Two, we invested heavily in product marketing & customer marketing and had some really good demos to help explain what AI can do for their business. We led our story with here’s what Computer Vision is, here’s what it can do for your business and here’s why you should care. Half our problem was to help the retailer see why they needed to move status quo. And you really need those first 2-3 customers in enterprise to help launch you.
Which brings me to three, without even knowing Customer Success is what we were doing, we helped our first few customers so much - white glove like I said - that they really stuck with us, are still with us, speak at our events and have become our evangelists. We invested a lot in building those evangelists.
- On the ICP question - it was actually simple. There was no way the big box retailers or the brands were investing in AI in 2016 It was the e-commerce, online, tech first folks who were going to invest in any of these features. This also meant competing with internal teams but we eventually won. So we replicated our success in that segment and went after the biggest online retailers as our starting point. Exec teams mostly.