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This week I want to talk about a framework I recommend when thinking through how to choose where to work. A lot of you have mentioned that transitioning careers and figuring out where to work next is a big motivator for reading this newsletter. Let’s dig into it.

Before jumping in, a reality check - it’s important to recognize that we’ve just undergone a massive shift in the macroeconomy. The trend of worshiping hugely unprofitable startups is over. The next decade of opportunities will come from *real* businesses (with real profits and real customers).

I’m a firm believe that you should evaluate career decisions with the same degree of rigor and thoughtfulness that funds apply to their investment decisions. In early stage companies, we talk a lot about product-market fit. When choosing where to work, I like to think about 3 other kinds of “fit.”

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I. Company-market fit: Is this company going to win?

When you work at a company, you are an investor. Just like all of the other investors. The difference is while they invest their capital, you invest your time. A much more precious asset.

You should gain both a quantitative and qualitative understanding of the company’s business.

Ask:

• Metrics: How is the company doing (traction, burn, valuation, etc.)?
• Vision: What is the strategy for how this company scales?
• Business Model: How does the business make money and is it sustainable?
• Competition: Who are the private and public competitors; why are they better or worse?
• Customers: Why do customers buy? Do they love the product/service? Where’s the proof?

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II. Person-company fit: Am I in a position to succeed?

Most people early in their career overvalue position and undervalue contributing to a winning team. Getting an additional 20%+ compensation at a flailing company is always worse over the long term compared to joining a rocketship. High growth companies unlock opportunities - they are the opposite of zero sum environments. That said, what you do in the short term matters. You want to be in a position to succeed.

Ask:

• What is the day-to-day responsibility of the current role?
• Who is the team I will be working with?
• What are the other teams I will be interacting with?
• What is the attrition rate of employees? Is the company a leaky bucket?
• Why do people love working here? Are those actually good reasons? (More substance, less perks)

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III. Person-problem fit: Am I in it for the long term?

Career gains are inversely correlated with career hopping. You should imagine spending the next 5 years working at the company. Knowledge and skill accumulation comes from staying past the honeymoon period (0-12 months). After that is when you get pushed, have to make tough calls and live with the repercussions of your decisions.

Ask:

• What skills are particularly valuable to this domain?
• Is this a problem / industry I care about?
• When it gets tough (it always does), am I motivated / excited enough to stick it out?
• Do I believe I can uniquely excel in this domain?

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The best way to bring rigor to your decision is to write a “Career Memo.” The exercise includes analyzing each opportunity you have across the 3 vectors and then comparing the full opportunity set.

Choosing the right place to work is an important first step in setting yourself up for success. You may not have perfect information to make your decision; but you should have perfect intent. That is fully in your control.

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Until next week,

Romeen

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