Jenn Harper sports a dark bob and a multicoloured top, smiling amongst palm leaves

Jenn Harper didn’t always have the goal of becoming the first Indigenous woman to have a business worth $1 billion, but today, she’s well on her way to making her dream a reality.

But before she became the Founder and CEO of Cheekbone Beauty, the first Indigenous cosmetics company in Canada, she had a literal dream: one that would change her life. In it, she saw Indigenous little girls with brown skin and rosy cheeks, laughing and covered in colourful lip gloss. As soon as she woke up, she wrote down "start a beauty business."

This powerful “aha” moment and Jenn’s Indigenous roots would become the foundation for her cosmetics company, which is now at the forefront of sustainable beauty and supporting Indigenous youth across Canada.

From a Personal Journey to a Purposeful Business

For Jenn, Cheekbone Beauty represents so much more than makeup—it's a path of healing and reconciliation. As she reconnected with her Anishinaabe heritage, Jenn learned about the residential boarding school system that had traumatized her grandmother, who was taken from her community at age six and forced to attend until she was sixteen.

"I wanted to turn this terrible narrative about Indigenous people into something that felt positive and powerful," Jenn explains to Good Housekeeping, reflecting on how understanding her family's history of intergenerational trauma coincided with her own recovery from alcohol addiction in 2015.

Jenn's personal journey deeply informs Cheekbone Beauty's mission: “to help every Indigenous youth see and feel their value in the world.” The company is committed to sustainability and giving back, donating a portion of profits to support Indigenous youth through education initiatives.

Building a Brand True to Her Indigenous Roots

When selecting a name for her company, Jenn put considerable thought into finding something that represented Indigenous identity while remaining accessible to a broad audience.

"I knew with the name that it had to be something that represented us as an [Indigenous community] but wasn't a word that no one could say or pronounce," she explains in an interview with the Government of Canada. "Anishinaabe people and many Indigenous groups and communities are known for having high, prominent cheekbones."

Her marketing research also revealed that people with high cheekbones are often perceived as more trustworthy—an important attribute for a new brand seeking to build consumer confidence.

This thoughtful approach extends to Cheekbone's products, which marry Indigenous wisdom with Western science. The company's in-house chemist creates formulations using local and sustainable ingredients, and their packaging prioritizes eco-friendly materials. In 2022, Cheekbone Beauty received B Corp certification, affirming their commitment to social and environmental responsibility.

Sharing Her Expertise Through The Forum

As Cheekbone Beauty has grown into a successful brand, Jenn has emerged as an influential voice in the entrepreneurial community. She now shares her hard-earned expertise with other aspiring business owners through The Forum, a national organization dedicated to unlocking access to wisdom, financial, and social capital for women entrepreneurs across Canada.

As a long-time Mentor and former E-Series speaker with The Forum, Jenn offers invaluable insights drawn from her experience as an Indigenous woman entrepreneur who successfully navigated the challenges of building a purpose-driven brand in a competitive industry. Her willingness to guide others reflects the values that underpin her business: community support and paying forward success.

"When you know someone's story, you can then empathize with them," Jenn says, highlighting the importance of sharing experiences across different communities—a philosophy she brings to her mentorship role at The Forum.

Through her involvement, Jenn’s inspiring the next generation of women leaders and using her experience to provide the kind of candid guidance that’s invaluable to other women who’ve taken the entrepreneurial leap–particularly benefitting those from underrepresented backgrounds who face similar barriers to the ones she overcame.

Overcoming Challenges in a Competitive Industry

Entering the beauty industry presented a set of specific challenges for Jenn as an Indigenous entrepreneur. "Some of the biggest hurdles of being an Indigenous entrepreneur and a woman-owned business is the lack of representation of people who look like me in mass media and pop culture," she shares with EDC.

Securing capital was another significant obstacle. When Cheekbone Beauty was ready to expand into larger markets, particularly the United States, Jenn found herself with a solid product and business plan but lacking the necessary funding. Through connections made with Raven Capital Partners, an Indigenous-led Canadian venture capital fund, and later with Export Development Canada, Cheekbone Beauty was able to secure the financing needed to pursue new opportunities and scale operations.

Creating Impact Beyond Beauty

Jenn's vision for Cheekbone Beauty has always extended beyond profit margins. As of 2023, the company has donated over $250,000 to various causes supporting Indigenous communities, “including the Navajo Water Project and educational funding for Indigenous youth.”

The cosmetics company created the Cheekbone Beauty Scholarship Fund to support Indigenous students in their post-secondary education, with 100% of proceeds from one product every year being donated.

"This is important because Indigenous culture suggests that success is not determined by the amount of money that is made, but by how you impact your community," says Jenn.

This commitment to community impact was also dramatically demonstrated in 2022, when Cheekbone Beauty launched the #GlossedOver campaign in recognition of Indigenous History Month. The campaign featured a line of “unsellable lipgloss,” inspired by contaminated water—a crisis affecting many Indigenous communities across Canada—to raise awareness about a lack of clean water access.

Maintaining Vision While Scaling

As Cheekbone Beauty continues to expand, with launches in major retailers like Sephora and Well.ca, along with collaborations with global brands like Mattel's Barbie, Jenn remains focused on her commitment to the company's founding principles.

"Our vision and mission will never change,” she affirms, “which is helping every Indigenous kid on the planet see and feel their value in the world.”

This clarity and commitment to purpose has guided Cheekbone Beauty through its growth stages, from an online direct-to-consumer model to its current presence in hundreds of retail locations across North America. The company continues to innovate with new sustainability initiatives and products that celebrate Indigenous culture and wisdom.

Looking Ahead

Through her journey with Cheekbone Beauty, Jenn has not only built a successful business, but created a platform for representation, sustainability, and positive change.

By sharing her expertise through The Forum and other platforms, she continues to amplify her impact—proving that when women entrepreneurs lift each other up, they can transform industries, uplift their communities, and create meaningful change that extends far beyond their individual success.