This article originally appeared in the Winter 2026 issue of the Gaynor Gazette.
Jaclyn Dobish has been at Gaynor since 2014, after deeming Gaynor the “just right” place for her to work in special education. After so many years at the school, Jackie has not only seen students grow and change, but teachers as well. Jackie and her co-teacher, Jacqueline Kolbert, were part of the pilot group for the Co-Lead model, and are known for their strong partnership in Room 404; so much so that they are colloquially referred to as “the Jackies.”
For our latest installment of “Five Questions With,” we sat down with Jackie to learn more about her experience at Gaynor, her love of Orange Cluster, and the way the Co-Lead model helps set students up for success.
What was your journey into teaching like, and how did you find yourself at Gaynor?
I graduated from Binghamton and I didn't really know what I wanted to do. I was a human development major, but I decided to go straight to grad school [at Hunter] for general and special ed. I worked in a different New York City private school for two years, but it was not special ed, and I felt like that was what I was missing. So I came to Gaynor, I met with Scott [Gaynor] and Yvette [Siegel-Herzog], and it just clicked right away. And that's how I've been here ever since!
What keeps you coming back to work every day?
I feel like the best part of Gaynor for me has been that I was here when I was single, I was here when I was engaged, then I got married, had two kids, and I'm still here. Gaynor’s been a part of my life for 12 years, so it's been a long time. Every day is fun. Every day is different. I know at some schools or some jobs, you're waiting for the day to end, but here there's never enough time in the day to get done what you want to get done. And I think [Orange Cluster] is a very organic spot for me. I don't know if it necessarily is something specific, but I think the students are at the just right age for me in terms of maturity level. They're independent. They can go to the bathroom and wash their hands by themselves, but at the same time, they still need help with certain things. So they still need you in some ways for support that older kids would not. It's just a nice, good, sweet age. I think Orange is where I'm meant to be.
Do you have a favorite student story?
I couldn't think of one favorite student story, but I think that every single year, I say to myself, “Why didn't I start a book of writing down the funniest things that kids say?” Because there are so many of those moments throughout the day where you want to jot down a quote because kids just say the best things. And if I did do it, I probably would have a very long book by now!
But if I had to pick a highlight, I would say the winter concert's always the best. The kids hear about the winter concert early on in the school year and they feel scared, they're nervous, they have all the feels. But they always pull through, and they always shine, and it's always the best thing to see. I think that because of who we are and what we do, we're always thinking of the “what if.” And then it's one of those moments where you're like, oh, we didn't even have to think of any of those what ifs because they just did it and they rocked it. So it's probably one of the best moments of the year for sure.
You’ve been working as a Co-Lead teacher with Jackie Kolbert for five years now—what do you enjoy about the Co-Lead model and working so close together in the classroom?
I think the coolest part for the two of us was that for so many years we taught across the hall from each other, and we were always bouncing back and forth into each other's rooms asking each other questions; “Do you have this game I could borrow? Do you have an idea for this activity? What do you think I should do about this?” And now it's just automatic that we're together, which is so special. It helps that we get along really well. The kids know that we're equals and we really support each other through anything.
I think that the most important piece is that we have very different strengths and we have very different approaches to things, which is amazing because the kids can really get the best of the both of us. Our co-lead model match is going strong, so it's nice to see. At this point, I feel like there are so many of those moments where we finish each other's sentences, and we think to ourselves, “Oof, that's so embarrassing.” We bounce off of each other really well, and I think the kids view us as a very cohesive unit, which is really helpful.
For our latest installment of “Five Questions With,” we sat down with Jackie to learn more about her experience at Gaynor, her love of Orange Cluster, and the way the Co-Lead model helps set students up for success.
What was your journey into teaching like, and how did you find yourself at Gaynor?
I graduated from Binghamton and I didn't really know what I wanted to do. I was a human development major, but I decided to go straight to grad school [at Hunter] for general and special ed. I worked in a different New York City private school for two years, but it was not special ed, and I felt like that was what I was missing. So I came to Gaynor, I met with Scott [Gaynor] and Yvette [Siegel-Herzog], and it just clicked right away. And that's how I've been here ever since!
What keeps you coming back to work every day?
I feel like the best part of Gaynor for me has been that I was here when I was single, I was here when I was engaged, then I got married, had two kids, and I'm still here. Gaynor’s been a part of my life for 12 years, so it's been a long time. Every day is fun. Every day is different. I know at some schools or some jobs, you're waiting for the day to end, but here there's never enough time in the day to get done what you want to get done. And I think [Orange Cluster] is a very organic spot for me. I don't know if it necessarily is something specific, but I think the students are at the just right age for me in terms of maturity level. They're independent. They can go to the bathroom and wash their hands by themselves, but at the same time, they still need help with certain things. So they still need you in some ways for support that older kids would not. It's just a nice, good, sweet age. I think Orange is where I'm meant to be.
Do you have a favorite student story?
I couldn't think of one favorite student story, but I think that every single year, I say to myself, “Why didn't I start a book of writing down the funniest things that kids say?” Because there are so many of those moments throughout the day where you want to jot down a quote because kids just say the best things. And if I did do it, I probably would have a very long book by now!
But if I had to pick a highlight, I would say the winter concert's always the best. The kids hear about the winter concert early on in the school year and they feel scared, they're nervous, they have all the feels. But they always pull through, and they always shine, and it's always the best thing to see. I think that because of who we are and what we do, we're always thinking of the “what if.” And then it's one of those moments where you're like, oh, we didn't even have to think of any of those what ifs because they just did it and they rocked it. So it's probably one of the best moments of the year for sure.
You’ve been working as a Co-Lead teacher with Jackie Kolbert for five years now—what do you enjoy about the Co-Lead model and working so close together in the classroom?
I think the coolest part for the two of us was that for so many years we taught across the hall from each other, and we were always bouncing back and forth into each other's rooms asking each other questions; “Do you have this game I could borrow? Do you have an idea for this activity? What do you think I should do about this?” And now it's just automatic that we're together, which is so special. It helps that we get along really well. The kids know that we're equals and we really support each other through anything.
I think that the most important piece is that we have very different strengths and we have very different approaches to things, which is amazing because the kids can really get the best of the both of us. Our co-lead model match is going strong, so it's nice to see. At this point, I feel like there are so many of those moments where we finish each other's sentences, and we think to ourselves, “Oof, that's so embarrassing.” We bounce off of each other really well, and I think the kids view us as a very cohesive unit, which is really helpful.
Room 404 Dream Team: Jackie Dobish (left) with Jackie Kolbert (right).
What do you do outside of Gaynor?
Having two kids definitely takes up a lot of my free time. My son, Leo, is turning five next month, and my daughter, Liv, just turned two in December. I would say a normal weekend is us going to a play space or doing something fun for the kids. Lots of birthday parties to go to. We have a dog named Archie and we like to play with him all the time. My husband, the kids, and I love spending time at the beach, especially during the summers off from Gaynor. We love Atlantic Beach on Long Island. So that's where you can find me, posted up in a beach chair under an umbrella.
Having two kids definitely takes up a lot of my free time. My son, Leo, is turning five next month, and my daughter, Liv, just turned two in December. I would say a normal weekend is us going to a play space or doing something fun for the kids. Lots of birthday parties to go to. We have a dog named Archie and we like to play with him all the time. My husband, the kids, and I love spending time at the beach, especially during the summers off from Gaynor. We love Atlantic Beach on Long Island. So that's where you can find me, posted up in a beach chair under an umbrella.
