Tweet by gokulr

July 3, 2026

Three non obvious things: 1. Find someone who can easily switch between strategy and execution, between the clouds and the dirt, between the board room and the daily standup, between the 60,000 foot view of the business and the lowest level of execution detail. I feel this is a non negotiable that people overlook. You want a doer, not just a talker, someone who hasn’t been lulled into the complacency of becoming a capital e “Executive” but can’t actually drive projects themselves. Whatever you do, don’t compromise on this. Execs are great talkers, so don’t get seduced by this. Drill into multiple levels of detail on their work and see if they understand it and can explain their work at that level. 2. Find someone who can deeply engage with both the product development team and the business / sales team. Yes, it’s likely they will lead one or the other, but they can’t be a single dimensional person who doesn’t understand product or doesn’t have a strong opinion on product. In other words, don’t hire a person who can’t truly engage with product and Eng as an equal. Have them meet 1:1 with key product leaders. Bring them to a couple of product sessions and see how they engage. Have a product centric dialogue with them. If you don’t get inspired or energized with their product vision or thinking, likely pass. 3. Remember that this is a bespoke role. The right near peer for each company / founder is unique and one of a kind. Eric, Sheryl, Keith, Christopher and Emilie are all very different from each other, both in styles of operation and personalities, but all wildly effective in their own way. Make sure your near peer is a fit for YOU and YOUR company. Understand their style of working by speaking with as many coworkers as possible. Make sure they pass the airport test with you. Meet with 5 founders who’ve successfully hired near-peers (and the near-peers themselves) to undestand the hiring process and how they figured out this person was “the one”.

Author
gokulr
Date
July 3, 2026
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