All startups look the same on the outside. You see a nice website and a lot of passion, especially when you’re in the Seed and Series A stage. The founders are still selling at this time and are looking to make the first sales hire to really get things going and build out their Go To Market (GTM) team.

From a sales perspective, there is an enormous risk in being the first sales hire because all revenue generation is on you and the company hasn’t figured out the selling process, that is why they hired you. At that point, there were a few critical things Prodigal did during the interview process that really impressed me.

Humility is one of the main things I look for in leadership. Especially when the CEO and Founders don’t have a sales background. Shantanu, my CEO, was incredibly humble on the first call and admitted sales wasn’t his strength which is why he was hiring for this position. Many CEOs believe they can do it all and don’t want to openly admit areas they don’t excel in which causes unnecessary tension within the company.

That was the first major check in my box. I knew the leadership team was humble and open to learning from others. This is critical because I was hired for my expertise which means I’ll respectfully challenge the way things are done in order to find the most optimized solutions. That can’t happen when major egos are present.

Secondly, and arguably just as important, was the product. Did it solve a true challenge or was it more of a nice to have? Given our industry and how easy it is to get sued over a minor violation, I was confident we were solving a major challenge. After that initial pass, it came down to how good is the product. Are we one of the top performers in the category or not? This is critical because we don’t have a massive brand presence yet so the product does need to sell itself once you get into the sales cycle.

I continue to be impressed with how advanced the product is and how fast the engineering team works. They’re truly customer-centric in their design and approach to tackling new features. Also, the maturity of how they build out their product and how quickly they move is usually seen in much more mature companies.

That was another major check in my criteria list. At this point, I realized that we had great leadership in place who was open to doing things differently and I knew we had an amazing product. All that was needed was a great Go To Market (GTM) strategy.

My background in startups to Fortune 50 companies paired nicely with what Prodigal was looking for. They were seeking someone to truly own the sales process and build out the GTM strategy which is exactly what I love doing.

At that point, I was fully convinced that Prodigal was the right choice for me and haven’t looked back since.

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