“Sorry for the delay here. I’ve been cramming to package up the last of our holiday push at both TRX and Apply.”
That was how I opened an email to the founders of a restaurant concept who had asked me to help think through their first real technology leader.
They had a title in mind. I thought the more useful question was what they actually needed this person to do.
The company was early. The leader needed to be able to take the concept through the next two or three stages, not just fit the company as it existed that week. That meant understanding the actual technology, being able to review code and integrations, and knowing how to build a team without hiding behind one.
It also meant having a point of view about the product roadmap. What should be built? What should be bought? What had to work now, and what could wait?
I broke the leadership question down too. Did they need a leader in the field, a player-coach, an organizational builder, or someone whose best skill was getting a team to believe in the direction? Those are different people. Calling all of them a CTO does not make them interchangeable.
The industry background mattered less to me than the system they were building. If the important experience was consumer transactions, mobile ordering, and receipts, that pointed one way. If the difficult part was physical automation inside the operation, that pointed somewhere else. “Restaurant experience” by itself did not answer much.
Then I put a heading in the email: It is not IT.
The job was not keeping laptops connected and software licenses current. Technology was part of the consumer experience, the unit economics, the operating model, the brand, and the product. The person leading it needed to understand that whole shape.
This was happening while TRX was working through digital product and ecommerce systems and Apply was finishing a holiday run of products and small retail experiments. I was dealing with the same mix of product, software, and operations every day.
I offered to vet candidates, join interviews, or help the founders build an interview process that would let them do it themselves. We put a follow-up on the calendar for January.
Wednesday was better for me.
Track practice was Tuesday night.