Part 3: Should You Become An Early Business Hire?

Our previous post proposed that properly defining and renaming the “hustler” role will benefit both individuals and early-stage startups. We’re calling this role an “early business hire” (EBH).

To understand the current market, we talked with 30+ startup CEOs and found more than half had hired for this role. Most of this hiring, however, was done without scoping or publicly posting a job rec. We also found that many successful Silicon Valley VPs and Founders started out in one of these roles.

Picking the right next role can have profound implications for your career trajectory. How do you know if this role is right for you?

Here are some questions to help you understand the role more deeply so that you can understand how it matches up with your abilities and career aspirations.

What makes for a successful EBH?

An EBH is successful when s/he helps a startup achieve product-market fit. You do this by deeply understanding the “market” side of the equation, and by taking those market insights back to your product team, you can jointly work on “fitting” the product to the market.

To be successful in your work, you’ll need a certain combination of knowledge, skills, and attitude.

Knowledge
You need to understand people and how they make buying decisions, both individually and within an organizational structure. This will allow you to glean insights from customer interactions and also manually generate revenue via sales and partnerships. In addition, you need to understand startup best practices and know which tools can help you leverage your efforts to shrink entire departments at a big company into a one-person job.

Skills
You’ll carry out all kinds of day-to-day activities to help find product / market fit including actions at every stage of the conversion funnel: demand generation, qualifying, closing, onboarding, and success. Example activities include: content creation, list-building, qualifying phone calls, in-person sales meetings, writing and deploying an onboarding drip email campaign, creating tutorial videos, etc.

Attitude
If you are a successful EBH, it’s because you think like an owner: no one is going to solve this problem for me). When we asked Founders what they were looking for in an early business hire, they said: scrappiness, drive, determination, comfort with ambiguity // Flexibility and adaptability // Athlete. Ability to wear multiple hats. // Hustle & Work Ethic // leadership, proactivity, hustle // Ability to get things done // a mini CEO :)

Do those traits resonate with you?

What does the career trajectory of an EBH look like?

If you are able to succeed in your early business hire role, the company will scale and eventually you’ll be forced to make some decisions. You have quite a bit of optionality. Below are three scenarios you could find yourself in:

1. Specialize functionally — In taking an early business hire role, you will touch many aspects of the business, from sales and marketing to customer success and product. In your work, you may find that you naturally gravitate towards one of these functions. If so, you can choose to specialize in one of these areas, either growing into a mid-level role at your startup or (assuming the company fails) joining a mid-stage company in a mid-level role now that you’ve gained some entry-level experience. Andrew Dumont and Cristina Cordova are good examples of this model.
2. Continue problem-solving — If you are able to succeed in your early business hire role, the company will move beyond the search for product-market fit and into building the machine mode. For the functional areas of marketing, sales, and customer success, the founders will look to bring in VPs with experience building out the machine. But this will leave new scaling problems to solve, things like HR, ops, new markets, etc. A founder will often start tackling these new challenge areas, and you as an early business hire can help solve these problems. This can eventually lead you to want to specialize in one of these later-stage functions, or to pursue a COO-style or GM role in a future company. Andy Sparks and Evan Moore are good examples of this model.
3. Rinse-and-repeat — You may find that you really enjoy the zero-to-one process of searching for product-market fit and want to do it again as another early business hire. Eventually you may want to do this for yourself by starting your own company. Ryan Delk and Scott Britton are good examples of this model.

How does the EBH role compare to alternatives?

When making a decision of what role to pursue next, you should definitely consider your alternatives. Here are three possibilities. I’ve listed their pros and cons as well as some questions to ask yourself:

Big Company — Google, Facebook, and other big companies hire lots of people every year.

Pros: Stability, role clarity, good comp, and work/life balance.

Cons: You won’t have context for why you’re doing what you’re doing, the pace of learning can be slow, and roles are often narrowly defined.

Questions: Do you get demotivated in situations where you lack influence in a decision-making process? Do you need context to do your best work?

Fast-growth mid-stage company — Join a company like Pinterest or Stripe that is post-pmf but scaling its value-delivery machine quickly.

Pros: Brand halo, quick escalation of responsibilities.

Cons: Difficult to get, narrow expertise often required

Questions: Am I competitive for one of these roles given my current skill set? Do I know that I want to specialize narrowly in a given function?

Start your own company — Companies cost almost nothing to start. You could start your own company instead of going to work for someone else.

Pros: Autonomy (until you get investors and employees), broad responsibility.

Cons: Incredibly high likelihood of failure, no one to learn from, and you only have so many swings at bat.

Questions: Do you have an idea that you’re ready to commit 5+ years of your life to? Do you think you’ll be more likely to succeed as an entrepreneur if you continue to build your skills and experiences first?

EBH sounds great. How do I prepare to become one?

In addition to attitude, there is a broad range of knowledge and skills you need to build to be a capable EBH. We’re currently working on a reading list that should get you started on this learning journey. Sign up below to be notified when we publish the reading list.

Tradecraft has helped 300+ smart, motivated people join the startup world. We’ve helped people from JP Morgan Chase, McKinsey, the U.S. Air Force, The World Bank, Google, Yahoo, etc. transition into roles at Clever, Doordash, Dropbox, Facebook, Medium, Optimizely, Segment, Uber, Udemy, and many up-and-coming startups. If you are interested in working with us, drop us a line.