Wilton’s Dina Bisson, founder of tree stumping business Rosie the Stump Boss, says “It’s a constant battle to prove my worth” as a woman in the male-dominated landscaping industry.
Bisson was laid off from her corporate job in March and “desperately needed to find something else”.
“Hats off to all stay-at-home moms, I am just not one of them”, Bisson explained.
The opportunity to launch her own tree stumping business presented itself mid-summer when Bisson’s father-in-law retired and sold the 65-year-old family tree business. Bisson had a hard time seeing the business go and launched Rosie the Stump Boss in August to further her father-in-law’s landscaping legacy, this time, through a feminist lens.
“I made the very conscious decision as a female to break into this male-dominated industry.”
When Dina’s husband, Serge Bisson, designed the company’s logo, Bisson says she was “100% deliberate” in choosing Rosie the Riveter to represent her brand.
“She’s an allegorical, cultural icon, she represents all the women in the workforce who stepped up when the men left for the military during World War II. She represents women’s independence and she is courage personified,” Bisson explained.
“I’m very emphatic when speaking about Rosie because she’s everything I want my girls to be. I have three daughters and I want them to see me doing what I’m doing. It’s really important to have positive images of powerful, intelligent women making change in the world,” she added.
Bisson is influenced by her mother who taught her to be a “strong-minded, fearless female” and Justice Ruth Bader Ginsburg, whose quote, “All I ask of our brethren is that they will take their feet from off our necks,” Bisson repeats to herself often.
Bisson hired Rebecca Kuijstermans as part of the Rosie the Stump Boss team, a deliberate decision she made to empower more women to enter the industry.
She knows stereotypes may persist and not everyone will embrace her or her business. Bisson said she’s “acutely aware of the brand I am embodying and promoting” and often worries that she is driving away customers that may not care about supporting women in business or trust a woman to do the job at all.
“There is always going to be some doubt in my mind that we weren’t chosen because unfortunately, someone thinks a man can do the job better.”

When talking about challenges, Bisson cited the physical demand of operating a stump grinder, a “3,000-pound metal wheel with teeth,” and the mental obstacle of knowing that she is one of the few females in a male-dominated field. She cited the statistic that men own 80% of landscaping companies and are responsible for 80% of landscaping revenue.
“It’s a billion-dollar industry, and as a woman, we just want a piece of the pie, if not the whole pie, but that comes later,” she said.
Bisson has completed 25 tree stumping jobs since mid-August, a goal she is proud of. She has long-term goals to franchise the business but for now, is just hoping to get another 10 customers.
You can follow Rosie the Stump Boss on Facebook and Instagram.
So awesome, you go girl!
Way to go, so proud of you!
Good luck with everything. I have been grinding stumps for over 30 years now.