Jenna Chesley "Uptown Beauty"

Jenna Chesley is the owner and operator of Uptown Beauty in Waterboro, Maine. After years of building her skills and experience in the beauty industry, she took the leap to open her own business in March 2025. Drawing from everything she learned along the way, Jenna has created a salon focused on consistency, professionalism, and helping every client leave feeling their best.
Guided by her signature motto, "Grit, Grace & Gloss," Jenna's true passion is the salon industry itself. She loves everything from creating beautiful transformations and helping clients build confidence to continuing her education and mastering new techniques. Uptown Beauty offers a full range of services, including haircuts and color, brow lifts, brow tints, brow waxing, Brazilian waxing, and much more. While she also enjoys cutting men's hair, her focus is on providing exceptional salon services for everyone who walks through her doors.
Beyond the salon, Jenna is passionate about supporting other women in business. She is currently organizing Uptown On Maine, a networking event designed to connect, encourage, and promote female-owned businesses and entrepreneurs throughout the region. Hosted at Uptown Beauty in Waterboro, the event aims to strengthen the local business community by creating meaningful relationships and opportunities for women to grow together.
In this episode of The 207 Collective Podcast, Jenna shares her journey to becoming a successful business owner, the lessons she's learned along the way, her love for the beauty industry, and her vision for building a stronger community of women entrepreneurs across Maine.
Book an appointment with Jenna at Uptown Beauty:
https://uptownbeauty207.square.site/