Cheekbone Beauty Founder Jenn Harper on Building a Brand with Purpose


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[vc_row][vc_column][vc_column_text]People often say “dream big,” as an analogy to stay ambitious and not set limits on yourself. For Jenn Harper, dreaming—literally—was the catalyst for the courage to leave her job in sales and marketing to begin an entrepreneurial journey and eventually launch Cheekbone Beauty. 

A makeup company that represents so much more, Cheekbone Beauty has been dedicated to supporting and creating a positive impact on Indigenous youth since its inception in 2015. Harper, who has Anishinaabe roots, wanted to create a brand where Indigenous youth could see themselves represented.

The world didn’t need another lipstick brand that was just raking in profits for no good reason,” says the founder. 

The company has evolved into a culmination of all things important to Harper, focusing on sustainability, innovation, and Indigenous representation and support. 

Notably, in March 2020, Cheekbone Beauty released its first original formula, SUSTAIN Lipstick. Created with minimal biodegradable packaging and sustainably sourced ingredients, it’s the first step in what Harper hopes will become the norm for beauty brands, at least for her own.

“I realized early on that for us to be truly successful in this industry and make a difference and make a change, we would have to get serious about really making our own products, our own formulations, with our own chemists,” says Harper.

Four women, standing together and smiling. Cheekbone Beauty founder, Jenn Harper, and three models.
Jenn Harper (second from left) with Cheekbone Beauty models, all of whom have Indigenous backgrounds and were chosen for the work they do in their communities.

And while she’s grown the company to have a community of over 115,000 people on Instagram, with customers from around the globe, becoming an entrepreneur was something that never crossed her mind until that fateful night and dream. Harper laughs and says that when a friend told her about an entrepreneurship class in high school, she asked, “What the heck is that?”

Despite having no experience in building a business, let alone the beauty industry, Harper is to on her way to building a makeup empire, all while doing good in the world, and she has no plans of slowing down.

“For me as an Indigenous woman, I really have this goal to show our youth in our Indigenous communities that when you have an idea and you do the work, despite life experience you can create your future based on how much work you put into something and what you’re willing to sacrifice,” says Harper. “Every Indigenous kid on the planet can build the life of their dreams.”

For this week’s Entrepreneur of the Week spotlight, Bay Street Bull spoke with Jenn Harper, Founder of Cheekbone Beauty, about Indigenous representation, building a brand with purpose, and innovation in the beauty industry.[/vc_column_text][vc_text_separator title=”Q&A” color=”custom” border_width=”4″ accent_color=”#e84a9e”][vc_column_text]How did you transition out of a sales job in Toronto to becoming an entrepreneur and building Cheekbone Beauty?

It was quite the process. The original idea for Cheekbone literally came from a dream. It was a dream where these little Indigenous girls were covered in lip gloss and I saw this immense joy on these little girls’ faces. At that point, I was already thinking about leaving the career I was in—I didn’t love that job as much as I once did. So I woke up that night, grabbed my laptop, and started writing out all these ideas—which became what is now known as the business plan—and that was the beginning of it.

I took that idea and worked on it for all of 2015, into 2016. I read over 100 books about how to build a business because I had never done that before and I had never worked in the cosmetics industry.  At the same time, I was reading books all about Indigenous history in Canada, Indigenous stories from Indigenous writers, and learning about the residential school system. I had this reckoning of my own sobriety, learning about my grandmother’s history with residential schools and realizing how my people were so impacted and still are to this day.

I wanted to be a part of changing that narrative for all of us as a people and for the rest of the world to see the beauty of our culture. I wanted to help eliminate those stereotypes and show how we can truly become more empathetic as a society to all different kinds of groups of people when we learn about them.

During the development phase of bringing Cheekbone Beauty to life, were there any big hurdles in going from an idea to a product and a brand?

When you understand the manufacturing world, you realize that private white labeling exists in every category. Having come from a broad line distributor in the food world, I discovered that the beauty industry was the same way. When initially building Cheekbone, it was not hard finding manufacturers. Finding high-quality manufacturers where they share the ingredients they use? That was a bit trickier.

There are some manufacturers in Canada, but you’re paying a premium. As a business, you wonder, “Is my customer at the end of my market going to pay that premium because they’re getting Canadian made?” So there was a lot of decision-making around trying to figure out what the best solution was. 

The early stages were about testing and playing with the market and manufacturers and creating brand awareness and a community. With my background in marketing and the sales side of things, I knew that if I could create the brand, I would have the ability to sell those products. And oh my goodness—people wanted to buy our stuff! It blew me away that people were paying these premiums for our products. 

I realized early on that for us to be truly successful in this industry and make a difference and make a change, we would have to get serious about really making our own products, our own formulations, with our own chemists. I found a contract chemist and that was our first step into creating our own lipsticks, which is now known as our SUSTAIN collection. We learned a lot about stability testing and now we are building up the capabilities—we are even building our own lab right now! We know that to be a successful business, you need to have a strong R&D vision and mission. And so that’s where we’re focused right now as a brand.

And with your background in sales and marketing, where did the name Cheekbone Beauty come from?

I was listening to a lot of podcasts when I was in the naming process. I listened to one where Sara Blakely was talking about how she came up with the name Spanx and that the ‘K’ sound is something that people remember. So, I was obsessed with finding a ‘K’ word. All of a sudden, one day I was like, “Cheekbone.” I loved it.

Not only are Indigenous people known for having high cheekbones, but I did some research, and people with high cheekbones are perceived as more trustworthy.


I remember saying early on that if I empowered and inspired one person, I would feel like we’ve done our job. And from the number of emails and DMS and conversations I’ve had over the years, the response has been amazing. 

One story that I love to share is of a mom who adopted an Indigenous little girl and who purchased our product and got our postcard, which has five Indigenous models on it. The little girl came home and saw it and was just like, “Oh my goodness. They look like me!” In the mom’s email, she said she’d never seen her daughter that happy. 

I’ve also recently received emails coming from Alberta—and I didn’t grow up or live there, so I don’t know the relationship between Indigenous people and Albertans—but I’ve received emails from non-Indigenous people that live there and say that they’re trying to personally change their view of Indigenous people and the way that they have done that was by supporting Indigenous brands. And I think that is incredible to recognize when a change has to be made. I mean, we’re all imperfect human beings, so we all have things that we have to change, but I think that it’s powerful when someone is brave enough to speak up and say, “Look the way I have thought about your people for my whole life was wrong.” 

You’ve mentioned R&D in terms of creating the product, but Cheekbone Beauty is also very dedicated to sustainability with that packaging and the branding. Why have you chosen to hone in on sustainability?

It’s been challenging, but it’s very important. We went into this, knowing that there is no perfect answer for this, but there are certainly better ways to go about projects and that includes how we make, create and buy things in this world. 

Our investment group Raven Capital is building an impact project. So, as one of its invested companies, we will truly have data surrounding the impacts we’re making in certain areas. For us, it’s about how much impact are we making in the lives of Indigenous youth. Environmentally speaking, we want to know how much less of an impact we’re making on the planet with the changes we’re trying to make.

As an Indigenous business, we want to build our systems, like the concept of a B Corp, measuring sustainability, but through an Indigenous worldview, not a Western one. Of course, all of these things take time. So, we won’t know right away how much impact we’re making, or if we’re doing things the right way. We might have to make changes and pivot, but what’s important is just getting started and asking all of those really hard questions. 

You’re focused on sustainability and a great impact on the planet, but then also, obviously on Indigenous youth—Cheekbone consistently gives back to the community. Why was that important an important aspect to include in the company?

The only reason I built this business—aside from wanting a different job—was to make an impact on and support Indigenous youth. My original idea was to build a scholarship fund in my grandmother’s name—and that’s still a goal—but along the way, I realized how important it was to support the community. Through business, you can do good. The world didn’t need another lipstick brand that was just raking in profits for no good reason.

We’re proud that in 2020 alone, we hit over $100,000 in cash and in-kind donations to different Indigenous youth organizations. That’s part of the work that we built-in, and I’m glad that we did. I think that [supporting your community] can be part of your business from the moment you exist.

Another thing that Cheekbone Beauty does is the Pink Feather campaign. Can you give the back story behind that?

Like a lot of e-commerce businesses, you start and you’re a solopreneur—all by yourself. In the beginning, it was family and friends that had ordered, and that was amazing. As we grew, people all over North America, even into Australia, were ordering products. I was like, “This is incredible!” And I felt this immense gratitude. 

As a business, we layer this concept of love into everything that we do. Sometimes we always think of love as this romantic thing, but love is truly just this exchange that we can have from one human to another. So we look at love as a verb here at Cheekbone Beauty; it’s always about action. 

With the pink feathers, we began to put those in orders early on, and it was just a small symbol and token of our love and gratitude back to the community that was supporting us because I was so personally grateful for their support. We still do it to this day, and I hope we always will. 

When we give it to them, we always say that they can give it to someone else or, or keep it. And it’s interesting because we see stories about people that have given it away to people that they want to spread love and gratitude towards. And then we see people that have collected them and made beautiful crafts, jewelry, and decorative pieces out of them. For me, it’s now the symbol of the love and gratitude that I feel for this community.

Photo of a woman smiling at the camera. It's Jenn Harper, Fonder of Cheekbone BeautyWhat’s one thing you know, now that you wish you knew at the beginning of your entrepreneurial journey?

I’m really open about saying I might never have got into the beauty industry. It is such a competitive space. It’s proven to be so challenging, but I also absolutely love it. I would say that not knowing things can be a superpower in some ways. Not knowing a lot of stuff has helped me in an industry that’s maybe always done things the one way, to do things differently. For instance, with regards to packaging and the things we’re trying to develop to use less packaging. I think someone that comes into a new industry has a great opportunity because they can see things differently.

What advice would you give to Indigenous youth who are aspiring entrepreneurs?

Just be consistent. Wake up every single day and do something. Work on the project or the plan or the idea that you have, keep moving forward that it will succeed. The only way it’s not going to succeed is when you give up. So, if you never give up and you’re consistent, it will work.

What’s next for Cheekbone Beauty? 

We are heavily in R&D mode. We’re so excited to invite the world into our space as soon as we can have visitors again. We really want to be transparent about our lab and how we make and create things. So we’ll be inviting the world into our space and, for the time being, that will happen through an online lens or social media.

I’m just excited to get in there! I have all of these incredible, crazy ideas of the things we want to make and create. I’m already envisioning our chemist saying, “No, we can’t do that. That won’t work scientifically.” [laughs].

There’s a lot of ingredients that Indigenous people have used for hundreds of years that have never been used in formulations. So, I’m excited to start working on some of those and bringing those to the table as well. There’s going to be a lot of things that maybe don’t work, but the exciting part is when you make something and you think it’s a failure, and then it turns out to be something amazing. So I’m just, I’m excited for all “what ifs” and getting into that lab.[/vc_column_text][vc_separator color=”custom” border_width=”2″ accent_color=”#e84a9e”][/vc_column][/vc_row]

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