Start Showing Up as Your Highest Self Now, & Land Brand Deals with Cassandra Dillard (@cassandraskyway)

Photos Courtesy of @cassandraskyway

Meet Cassandra Dillard, a social media expert turned influencer and founder of This Is A Girl’s Club, a community-driven brand empowering women. With six years of experience in the social media space, Cassandra's career has evolved from managing others' online presence to growing her own. In this conversation, she opens up about the challenges of building a personal brand, the transition from service provider to influencer, and her best advice for those looking to do the same.

Starting Small: The First Steps into Social Media

Cassandra's journey began with a social media management business that started within her own network; friends, family, and referrals through word of mouth. For years, she avoided promoting her services publicly, feeling hesitant to put herself out there. But as time went on, she realized that while she was helping others build their brands, she wasn’t giving the same attention to her own.

This shift in mindset led her to start posting about her business on her personal page, a move that felt terrifying at first. But with each post, her confidence grew. She spent a year using her platform to promote her social media consulting services before realizing she wanted even more: a brand that was authentically hers.

Pivoting to Personal Branding

Cassandra's wanted to move beyond being known solely as a social media expert. She craved creative freedom, to post about fashion, beauty, and This Is A Girl’s Club without feeling boxed into a niche. This realization pushed her to transition from a business-first approach to a more personal, influencer-driven brand.

The biggest lesson? Authenticity. Cassandra's believes that whatever you’re already passionate about in your daily life should be the foundation of your personal brand. Whether it’s ethical shopping, beauty, or lifestyle, staying true to your interests makes content creation effortless and engaging.

Monetizing as an Influencer

Initially, Cassandra's income came solely from social media management. But as she shifted into the influencer space, she began monetizing her content through UGC (user-generated content) and brand deals. Even though this was new territory, her years of experience working behind the scenes with brands gave her a strong foundation. Before signing a deal, Cassie advises influencers to ask brands about content usage.

“If a brand wants to run ads with your content, that significantly increases its value.”

She suggests negotiating based on factors like:

✔️ How many platforms the content will be used on

✔️ Whether it will be promoted as an ad

✔️ The duration of ad campaigns

“A lot of influencers undersell themselves. Ask brands about their plans, you might be able to charge more than you think.”

The Truth About Analytics and Growth

While many influencers obsess over analytics, Cassandra's takes a different approach. Instead of constantly chasing numbers, she prioritizes content that feels authentic and enjoyable to create. Her advice: when you’re just starting out, let go of the pressure to perfect your strategy.

“In the beginning, you don’t have enough data to know what’s working yet. So, experiment. Post what you love. Let go of the need for everything to be perfectly optimized, and just create.”

Letting People in on Your Journey

One of the most powerful aspects of personal branding is storytelling. Cassandra's has reinvented her social media presence multiple times, using the same account for makeup artistry, modeling, yoga, business, and now influencing. But the reason her audience has stuck with her through every pivot? Transparency.

Instead of quietly shifting directions, she brings her followers along for the ride, sharing her thought process and excitement about the changes. This open communication helps retain an engaged audience, even as her content evolves.

The Power of Bold Energy

For aspiring influencers, Cassandra's has one major piece of advice: act like the person you want to become.

“If you want to be an influencer with a highly engaged audience and brand deals coming in every month, start showing up as her now. Start emailing brands, start pitching yourself, because you never know who will say yes.”

Building a brand isn’t about waiting for permission. It’s about taking action, embracing your creativity, and stepping into the version of yourself that already exists in your mind.

Cassandra's journey proves that success in social media isn’t just about strategy, it’s about confidence, consistency, and owning your story. So if you’ve been waiting for a sign to start? This is it.

🎥 Watch Cassandra's full GRWM and influencer journey on Roe Magazine’s YouTube - 1st of March

Where to find Cassandra: Instagam

Where to find Roe Magazine: Instagram & Tiktok