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10 Questions to Ask Yourself When Evaluating a Company to Work For

Ryan Walsh, CEO and Founder
Ryan Walsh, CEO and FounderNov 30, 2022

Deciding on a company to work for can be tough. We all want what is best for our future and deciding to join a new company can have a big impact on your overall career trajectory. Will you go with the flashy startup, the well established behemoth, or somewhere in the middle? Below are some questions to ask when deciding on which company to go with. Oh, and if you are in this situation, you are lucky, not that many people even get a choice. 

10 questions you should ask yourself when evaluating a company to work for

Do they have founder market fit? (Has the founder been in the space before?)

This one might seem obvious but how many of you have actually researched the founders beforehand to see if they have worked in the industry before. Probably not a large percentage. This is one of the most important factors when looking at if a company will be successful or not. 

How big of a market are they are in?

Do you know the TAM or total addressable market? Especially in sales, knowing the size of the market can make the decision easier. If one has a $500M market vs one with a $20B, it’s probably best to go with the $20B market without looking at other factors. 

How acute is the problem they are solving?

Is there an actual problem they are solving or is more of a nice to have? The best products solve real problems.

Would you use this product personally?

This one is tricky for B2B products, but try and put yourself in the customer’s shoes and see if this is something you would use. Check out their competition, is there a competitor who is clearly winning the space and will be hard to out compete? This could go into your decision making process.

Was there a change in the world recently that makes this business more relevant now?

Are you in a hot industry? Was there certain laws that were passed that give the company a strategic advantage? Sometimes the fate of a company is down to timing. 

Is it a scalable business?

Is it an agency or some other service that does not scale easily? Most of the time in tech sales this will not be an issue because SaaS products are built to scale easily.

Can I see myself working there for years?

You want somewhere where you can grow professionally and somewhere where you won’t get bored easily. Try to look a few years into the future to see iff you can see yourself there. If the answer is yes, then things are looking good.

Do they have product market fit?

This is one is big. Very hard to market or sell a product that doesn’t have product-market fit (PMF). How do you know? Read reviews on the product, check their RepVue score for PMF, and try using the product yourself.

What’s the salary or compensation? 

This is one we all care about, and for good reason. Your time is valuable, so make sure you are being compensated fairly. To see the average salaries for people in the sales industry, go here.

Are the reps hitting quota currently?

Not many people ask this in interviews, but they should. Why work for a company where only 30% of the team is hitting quota? If you don’t want to ask or to double check what they tell you, you can check their RepVue profile to see their quota attainment stats. 

Before you take a leap of faith on your next role, ask yourself these questions and learn as much as you can about the company beforehand. It’s worth investing time upfront so you don’t get stuck at company you don’t like.

Best of luck on deciding which company to work for!

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