Learning at different stages

This blog has been quiet because I’ve much of my writing to my #hiringfriday substack. I did want to share my most recent newsletter, as I think it’s helpful for anyone thinking about joining an earlier stage company.

It’s a New York City heat wave, which means I’m alternating between hiding in my basement office and hanging out at the pool with my kids. Given the time of year, many of the calls I’ve been taking have been with graduating MBAs figuring out what’s next. I know that feeling well - I graduated from B-school with an internship that paid less than my pre-school consulting job (luckily it converted to full time).

One of the questions that often comes up is how to think about choosing a company stage to target.  There are the obvious factors - stability, compensation, role definition. But the way I often frame the biggest difference between early stage and later stage or public companies is one of “learning by doing” versus “learning by example.”

“Learning by doing” accurately describes all of my earlier stage experiences. You’re working with a great team, but they’re generally doing things for the first time. The upside is that you’ll probably have more responsibility and more room for growth. The trade-off is that you’ll have to become a bit of a Macgyver, figuring out how to get stuff done, and recognizing not all of your processes may scale.

“Learning by example” is what happens once you get to a company with product-market fit, and specialization. You’re probably taking a more defined functional role, and hopefully working for a manager who has more experience in that area and in leading people. You’re building for scale, and learning from folks who have done this before. The trade-off here is less flexibility and a more rigid (for a startup) career and promotion path.

Neither of these is better than the other - I’ve chosen both scenarios at different points in my career. If you’re job seeking, I encourage you to ask yourself what sounds most compelling to you right now, and use that to guide your search.