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Vlad Pick

Vlad Pick

Engineering Manager at Attentive; former CTO and co-founder of Tone Messaging (acquired 2021); angel investor and startup advisor.

Jun 3, 2026

13:43
So what is, what are some lessons learned that you could, you, um, you can share with founders who might be contemplating an M&A or, you know, how could th- how can they plan it and execute it better given what you have done?
13:57
Let me break this down.
13:58
In the context of seeking an exit for your company, I'd wanna admit that I was wrong about one thing.
14:03
So a year or eighteen months prior to us getting to this exit point, my co-founder and I were at a bit of a strategic impasse, which is like, what do we really double down on? What do we invest in? And my take was actually that we need to go very broad and build as many features as possible to satisfy as many users as possible, replicating a lot of what our competitors were doing so that we can be present in competitive deal situations.
14:28
And that made sense to my engineer brain because I'm saying, "Well, hey, I need to win more deals.
14:33
I need to grow faster.
14:34
What do I need to do? Why am I losing these deals? It's because maybe I don't have this, like, more robust feature here, or I'm missing this integration here." But my co-founder's perspective was, "No, Vlad, like, we're doing something really special.

19 MINS LATER

34:17
And, and if so, what is that? If the CTO's job has become so much simpler, does that argue almost for not even requiring a CTO anymore?

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