two employees co-working together at the same desk.

How To Get Through Your Company’s ‘Awkward Adolescence’ Stage

Deciding its time to hire help can be one of the hardest decisions for a founder — and other thoughts from heads at Clutch, LeagueSide, Proscia and GoCoach.

(As seen on

Most people’s middle and high school years can be some of the most awkward, unsure times in their lives.

But if you’re a company, that time in your development can come a little earlier — maybe a few years in when you’re not quite a startup anymore, but there’s still only a handful of employees running the show. 

That’s the theory of four founders at Philly Startup Leaders’ Founder Factory in November.

Kristy McCann Flynn, founder of reskilling company GoCoach; David West, cofounder and COO of health IT company Proscia; Evan Brandoff, cofounder and CEO of youth sports sponsorship company LeagueSide; and Ned Moore, chairman and CEO of customer marketing platform Clutch, talked about how they handled the first few years of their companies’ growth.

One of the hardest things to decide is when to stop doing everything yourself and to hire people to help with the workload, Brandoff said.

The youth sports company launched in 2015, and this summer moved into its own office at 24th and Walnut streets. At the time, it had 17 employees, but leadership was looking to add a handful of employees.

“In the beginning, you’re still doing everything, but when you realize you have no social life and there’s a lot you don’t know, it’s time to bring someone else in,” he said. “When we weren’t being very effective in the jobs we were doing, that’s when we knew.”

 Moore agreed, adding that it’s usually pretty obvious when there’s a job that needs to be filled. Usually, there’s just too much work to do, but that has to be balanced out with funding to hire someone full time.

 “It’s usually pretty clear where you need the help at different stages,” he said.

 But McCann Flynn went about hiring a different way. Her job training and reskilling startup, only about two years old, already has a handful of employees and about 150 coaches. She said that in order to build her business, she took out a loan and hired a bunch of people on day one.

One of the biggest thing she did that helped in the long run, she said, was seeking out and hiring people “a lot smarter than me,” she said.

 “You have blinders on, and you have this mission, but you’ve got to have people in your corner that you trust,” McCann Flynn said. “Because you’re going to make mistakes, but you’ll be better off with people you trust in your corner.”

So, maybe you know that it’s time to hire, but how do you know who will make a good fit on your small team?

 Brandoff said he looks for the owner vs. renter mentality in current and future employees. Essentially, some people are empowered to be owners of their position, while others might have a more 9-to-5 “renter” mentality.

LeagueSide also spends a lot of time during the interview process figuring out if the candidate has core values and fits with the company’s mission. Often, leadership is trying to figure out if the candidate has their own convictions and ideas or if they’ll just agree with whatever leadership is saying.

 “We love to embrace and work through conflict at LeagueSide,” Brandoff said. “So in interviews, sometimes we’ll say something that’s nonsensical to see if the candidate just agrees or if they push back.”

West said he and his team also spend a lot of time with candidates during the interview process, bringing them into the work setting. Every new hire should bring the company credibility when trying to raise money and should fit into the company’s culture fit and mission, he said.

“The right help is super important to us, we’re not just filling a void,” West said.

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