Maintaining Your Roots: How Cheekbone Beauty Keeps Grounded Through Organizational Growth


We all want to grow and be successful. However, sometimes businesses can be so focused on exponential growth that they forget to stick to their roots. We are inspired by companies that have demonstrated dedication, perseverance, and success while also staying grounded in the vision that got them where they are now. Meet Cheekbone Beauty: the Canadian, indigenous, female-led, and sustainable makeup company.


Cheekbone Beauty was started by Jenn Harper in 2016. Looking at the success of the brand, it is fascinating to learn that starting a cosmetics company wasn’t necessarily intentional.


Jenn Harper was driven by a dream; a dream of seeing Indigenous little girls covered in lipgloss. When she awoke from her dream, she realized that this was what she had waited for her whole life. As an indigenous female, she always wanted to do something that would reconnect with her roots, her culture, and her family. For the St. Catharines native, Cheekbone Beauty was an avenue to make those connections.


Looking at the growth of her company and the quality of their products, it’s impressive to learn that Harper did not come from a background of entrepreneurship or cosmetics. Driven by her dream, she was able to utilize a growth mindset throughout her process and learn along the way.


“I had no idea about anything about the beauty industry. If I'm being honest, if I knew what I know now, I might not have ever entered it. Being naive can be really a blessing in so many ways.”, said Harper.


When Jenn started Cheekbone Beauty, she was still working a full-time job in sales. Because she spent her weekdays working, she would work on Cheekbone Beauty during the nights or on weekends. She had no experience in manufacturing or formulating cosmetics. Jenn learned as she worked and as the company slowly started to grow. She admits it was harder to appreciate the growth at that time.


“Early on, it still did feel great, I'm like, oh my goodness, that's a brand we created.”, Harper said. “We created the brand, but now we're actually the makers of the products that we're putting out. It feels even better than before and just so exciting.”


Photo by Breann Rogers

Cheekbone Beauty has been growing substantially over the last few years, with many of its team members being there since the beginning. Their biggest achievement happened in September 2021: having their products carried online with Sephora Canada.


Sephora was something that Jenn had on her vision board since the conception of Cheekbone Beauty. She was first connected with Sephora in 2018, when she was then rejected from their accelerator program.


Jenn didn’t take no for an answer and kept the contacts she made during the process. Over the years, she would ask them what they wanted her to focus on. She started making her own custom formulas, packaging, and creating sustainability with her products. Using a growth mindset, she focused on how they could learn from each rejection to better the brand.


They got the news in January 2021 that Sephora.ca would be carrying Cheekbone Beauty products online. Their team immediately got to work to prepare themselves for this new growth, their biggest yet.


There were other times where Cheekbone Beauty could have seen massive growth. Jenn turned down many offers from large companies because they did not match her vision. She didn’t want her company used as a checkbox for a corporate agenda.


Makeup and photo by Paje Honor @HonorBeauty – Customer Experience Warrior, Rhea Carter modelling out SUSTAIN Lip Pencil in True Red.

Jenn’s Indigenous roots are a huge part of Cheekbone beauty. All of their values, principles, and policies are grounded in the Seven Grandfather teachings: love, respect, bravery, truth, honesty, humility, and wisdom.


“Sometimes it takes a lot of courage and bravery to stay true to that path. A lot of people that are probably far more successful than I may ever be, have said, ‘just make [cosmetics],” said Harper, “I say no, I think I need to stick on this because I'm in an industry that another beauty brand did not need to exist in. There's no way we need another regular old lipstick brand out there. What was missing was this representation of indigenous people and faces.”


For Jenn, that Indigenous representation is crucial to the roots of everything Cheekbone Beauty creates. It’s evident in their marketing materials, in the fact that they are a social enterprise giving back to the Indigenous communities, and even in their social media posts where they showcase their products on indigenous people of all different backgrounds and teach their audience Indigenous words.


“I think about empowering indigenous youth to come up with their own ideas and incredible businesses. We really want them to think about innovation, and think about how using our roots and the teachings that come from indigenous communities actually add a new perspective, a fresh view, on the way so many things have always been done. I think it's pretty apparent that many industries, not just beauty, need a little shaking up about how we approach business.”, Harper said.


Though she is proud of the growth her cosmetics company has made, Jenn is always looking forward. She hopes to soon get her products into the international market, especially in the United States. As a female entrepreneur, Jenn admits she often doubts herself, having to remind herself of her talents and her goals. She sets boundaries, making time to unplug every once in a while and tries to stay away from social media as much as possible.


As a leader, she has become better at celebrating growth and success because she believes that her team deserves to see praise for their successes. She is focused on hard work, healing, and growing her business to show her community what is possible.



Cheekbone Beauty’s ability to stay so tied to its original roots through growth is inspiring to all of us at Botree. Our talk with Jenn reminded us to stay connected to those pillars that matter to us, celebrate our growth, and persevere through challenges to reach our goals.


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