I get asked fairly frequently whether my short stint as an operator is beneficial as an early stage investor and whether I'd recommend other junior VCs take a similar path.

TL;DR, it's complicated, but let's start with what I learned & how to frame the decision.

Do I think operating experience makes you better able to pick winners? Probably not. But, do I think it makes you a better board member and thus perhaps better suited to win deals? Yes. For the purpose of this thread let's focus on what you'll learn.

I can distill down my learnings from my time as a Chief of Staff @Zuora to 3 key things:

1) Empathy. Building a company is incredibly hard and every company is messy on the inside. This helps you with empathy as a board member, and helps to avoid riding the emotional roller coaster. It also helps you realize how little the BOD really sees.

2) Organizational expertise. If you've spent your entire career in finance, your grasp of organizational structure and how teams work together is likely blurry at best, spending time in a company forces you to learn how teams and orgs work together.

3) People operations. Hiring is immensely important to any startup, but keeping employees happy, motivated, and fairly compensated is even harder. I got to see this in action and gained massive appreciation for how challenging this is.

You will also learn tons of tactical things -- I learned how to run annual planning processes, manage and measure KPIs, manage cross-functional projects, roll out comp plans, assess and augment GTM strategies, and so, so much more.

If you’re debating the jump from VC to operating, there are 3 questions I’d recommend asking yourself:

1) is there >0% chance you’ll love operating?
2) are you already on a partner-track path?
3) what specifically do you hope to gain and can you create a plan to achieve that?

If the answer to those leads you to conclude operating is the right path, narrow your search criteria to roles that maximize learning and access to leadership. For me these roles were: product, product marketing, strategic finance, corp dev, and Chief of Staff.

Lastly, I think operating experience is most impactful before you become a partner at a VC firm, and that doing a 1-3 year stint during your junior years makes the most sense.

This is a Twitter thread afterall, so in my brevity I’m sure I’ve missed many important caveats -- what would you add?