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  1. Intro: too many projects, not enough time At some point in Column Tax's lifecycle, we grew such that as co-founder & CTO (and responsible for Engineering, Product, and Design) I wasn't personally leading every project.

  2. When I went to hire my first person at Column Tax, Erik Goldman (co-founder of Vanta) shared this 4 step algorithm that I used and had all hiring managers who worked with me use as well.

  3. The unreasonable effectiveness of Problem/Solution Reviews The best AI Product & Engineering leaders are using Problem/Solution Reviews to ensure their team is actually building the right product instead of just building software for the sake of it.

  4. I started Column Tax in early 2021 and sold it to Aiwyn1 in late 2025.

  5. Huge thank you to Laura Hilton who helped me hire our VPE.

  6. In 2020 when we were at the beginning of our startup journey I had a conversation with Erik Goldman where he shared this process, which we used to start Column Tax.