Eleanor Dorfman: How We Scaled Retool to $50M ARR; Red Flags for Sales Hires | 20VC #925

Three, two, one, zero. You have now arrived at your destination. Eleanor, it is such a joy to do this. I've heard so many great things, especially from Jordan, who said you're an absolute star. And he desperately misses working with you. But thank you so much for joining me today.

Thank you so much. Working with Jordan was a has been, and I hope will be again, a highlight of my professional career thus far. So, the feeling is very mutual.

What incredible energy he has, I have to admit.

(laughs)

But I want to start a little bit on you. So tell me, how did you make your way into the world of tech and how did you come to be a sales leader, obviously, today at Retool?

Uh, I frequently use my own narrative as an example for folks on why careers are such a jungle gym versus a ladder. But I actually lived in New York before, which is where I live now, um, and I worked for the New York City Department of Education on a middle school literacy program. I was in schools once a week working on rolling out software to ensure sixth graders, or grade six, uh, are graduating reading on grade level. Um, and as part of that, we purchased, as a school district, a lot of literacy software, and I was very focused on rolling that out. I ran into a ton of infrastructure challenges. I wasn't able to connect the software to the underlying data systems. And students move in and out of classrooms in New York City more than one million times a day, and so the data became obsolete almost immediately. And I had bought really expensive software and the kids couldn't use it because they couldn't log in because we didn't know what school they were in, who their teacher was, what classes they were in, and then we weren't able to securely send that to the software providers. So I taught myself how to write scripts to try and improve this process. I think I violated quite a few student privacy laws, uh, with the very casual way (laughs) in which I was shipping off student data to third parties, which in hindsight makes me feel incredibly uncomfortable. Um, but I was looking, uh, one day for a solution to that and I found a tech startup that was solving that exact infrastructure problem called Clever. And I thought, "You know what? It might be a little more fun at this stage of my career to go work at a startup and to solve a problem I'm really passionate about." Uh, they didn't feel the same way. They rejected me three times, uh, because I did not have any relevant tech experience and I pronounced A-P-I "appy" on one of our first calls. Um, but ultimately agreed to give me a shot and take me on as an unpaid intern for three months. Uh, and, or maybe slightly paid intern, something that was a little dicey. Um, and I moved across the country, moved in with my mom's college roommate, Joan, uh, until I had a full-time job, uh, and worked there at Clever for three months. And then ultimately joined full-time and left as the, the head of customer success, um, solutions engineering and partner engineering.