Gaggle Speaks

Ideas, news, and advice for K-12 educators and administrators to help create safe learning environments.

Written by Lisa Railton
on July 21, 2021

Conor Flanagan has been with Gaggle for the entirety of his career, initially starting out as an accounting intern during his senior year in college. As our Finance Manager, Conor handles payroll, expenses, invoicing, and a variety of other financial tasks that keep things moving here at Gaggle. 


Start date: June 2, 2015

We asked Conor five questions to get to know a little more about him and his time with Gaggle. Here’s what he had to say:

What are three words to describe Gaggle?

  • Lifesaving: This is the number one word that comes to mind when I think of Gaggle. It’s the mission. Everybody in every department—whether it’s Finance, HR, Marketing, IT—does their part to try to reach that goal of saving student lives.
  • Rewarding: Every company needs business admin and accounting functions, and somebody’s got to do that for Gaggle. That’s what I’m good at, and if I’m going to do it, I would rather do it for a company that has a mission and makes a difference. I could do accounting anywhere, but it wouldn’t be as rewarding as doing it for Gaggle. 
  • Fun: One of our core values is “Work hard, play hard.” On a daily basis, employees at Gaggle come across very negative aspects of the world. Our Safety team members, in particular, are in the thick of it. Our leaders do a great job of keeping that in mind because they know the toll it can take. They make sure we have a fun, light environment to help escape the negativity, as well as gatherings and activities to get a mental reset. It’s necessary, and I’m glad we do it—and it makes Gaggle a really fun place to work. 

What drew you to Gaggle?
I was a senior in college looking for an accounting internship, and I knew the former CFO. At that time, the Finance and HR department consisted of just two people. They needed coverage for some invoicing and bookkeeping while one of those two was on maternity leave. I came in every day, did my work, and was never told to stop coming. The day after I graduated from college, my internship turned into a full-time role. The rest is history!

What have you gained from working at Gaggle?
Professionally, I’ve been able to work under two very different but very good CFOs. They’re both so good at this, and it’s been beneficial to learn and grow working under two people with different strategies. I’ve been able to draw and learn from both of them, and I can’t say enough good things about them. Personally, I really finished growing up at Gaggle. I was only 20 years old when I first started—I had my 21st birthday here. I had some of my first life lessons of being an adult at Gaggle. Being in the office and being able to talk to folks about things that were going on in my life and learn from their experiences really helped usher me in from a college student to adulthood. 

What is your proudest moment at Gaggle?
When customers come to Gaggle outings is when I’m most proud. Internally at Gaggle, we’re constantly reinforcing the fact that we’re saving students and how needed the work we’re doing is. We also often get follow-ups on students who were in crisis from our district partners, who will let us know the students are now doing well. But when a superintendent comes and stands in front of all of us to share their personal experiences, you can tell how much they care about and personally know that student who was saved. When they then thank us for everything we’ve done, that really hits home. You can tell that superintendent is genuine—they’re the one getting the call at 2:00 in the morning to alert them about a student in crisis. Hearing about Gaggle’s impact right from the source makes me proud. 

What is your favorite memory at Gaggle?
My favorite memory at Gaggle is the old Bloomington office. It was such an unconventional corporate office space—it kind of has to be when you do what we do. Most of what’s on people’s screens is already considered inappropriate given the nature of what we do. The content we flag and alert schools about wouldn’t be present at another company, so it had to be an unconventional office environment. When you see all of the bad stuff, we had to keep things light and fun. Being in that office with the people at Gaggle, we really had a group that was the most unique, creative, caring bunch of people who made it fun to come into work. The atmosphere made it fun to come to the office and fun to collaborate. There was never a dull moment, and that’s how people become more than just co-workers.

Gaggle has been Conor’s first—and only—corporate workplace since college, and he’s watched the company grow considerably over the years. “Gaggle is all I’ve ever known—I can’t even compare it to another company,” he said. “We really do have some of the most genuine and caring people here. I’ve developed friendships that will last forever.”

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