Alessandro Chesser was Carta's first sales hire and built the team from scratch to hundreds of reps over eight years, scaling the company to $300 million in annual recurring revenue. He started by selling subscriptions at $1,000 a year, gradually raising prices as he found product-market fit, then pushed for aggressive hiring when competitor Zenefits threatened. After leaving, he started Get Dynasty to help founders with Qualified Small Business Stock benefits.
Welcome to another Founder Wisdom podcast. We have Alessandro Chesser with us today. He's helping founders get more QSBS at Get Dynasty. He's an ex-Carta in Orinda, California. Alessandro, welcome to the pod. Tell us a bit more about yourself and what you've been up to.
Yeah, thanks for having me. You know, career salesperson, started out at Carta as the first sales hire in 2014, ended up becoming VP of sales. Sales and stayed there for 8 years helping bring the company from $0 to $300 million ARR and then left to start Dynasty.
Yeah, Carta is a giant. How did you scale or help scale it to $0 to $300 million? What's the sales playbook to achieve that?
You know, it was just day by day, you know, helped the You know, sell the first, you know, 30, 40, 50 subscriptions, you know, found the price point, you know, kept pushing price up, start, you know, first subscription was $1,000 a year, then $2,000 a year, and then kept pushing the prices up. And then got to the point where I personally generated like a couple hundred thousand dollars in one month in new ARR. And then I was talking to, at the same time, there was a really hot company Zenefits, you know, was blowing up. And I read an article about Zenefits hiring 100 or 200 sales reps. And I went to our CEO, Henry, I said, Henry, we can replicate this. We should do the same thing. We should hire 100 sales reps. And he's like, okay, well, let's start with 8. He's like, go hire them. And that's what started. And from there, you know, got to the point where I had close to a couple hundred people reporting to me, a team that I built, you know, pretty much brick by brick. I ended up managing not only sales, but I also had onboarding and customer support and relationship management evaluations. And so I built a pretty big team and I started floating around and doing different things. And by the end, I was mainly just building the new businesses and helping find product-market fit for all the new businesses that Carta was building. But I got to a point where I just, uh, you know, I already have too much skin in the game at Carta, and so I decided it was good to go diversify and, uh, you know, take my experiences and start my own company.
Man, that is crazy. Um, yeah, crazy playbook, right? Like, so the new reps, how would you onboard them? How did you make sure they would be successful? What percentage were successful, right? And, uh, yeah, what were their quotas? What are your secrets there?
Yeah, so I think, you know, Henry RCO, he wrote this blog post on how to hire, and he had this really strong opinion that nobody was good at hiring. Hiring was always a coin toss, regardless if you do all these tests and, you know, Google and Facebook-style interviews. Nobody was successful at it.
