Brand Message & Content Marketing Strategy

BRAND: Regina Lawless

SERVICES: Brand Message & Content Marketing Strategy

Author, leadership coach, and former Head of Diversity, Equity, and Inclusion (DEI) at Instagram, Regina Lawless is also the Founder of Bossy & Blissful, a membership for Black women leaders to connect and grow alongside each other.


Although she already had a good number of followers from her time at Instagram, Regina Lawless was solely using the platform as an online diary – which meant her personal brand was getting lost in the shuffle.

Looking for a new way to step up her personal brand and introduce her new business at the same time, Regina wasn’t sure how to talk about her expertise or herself in a way that felt genuine – which resulted in not posting anything online… stopping her from growing her reach, creating a community of Black women executive leaders, and sharing her insights and experience.


With this in mind, Regina wanted to not just exist online… but make a significant impact. This lead us to create a list of specific goals we wanted to achieve:

  • Devise a strategy to ‘relaunch’ her personal brand on Instagram.
  • Outline a 6-12 month plan for Bossy & Blissful’s brand positioning and growth.
  • Gain a comprehensive understanding of branding and how social media can be harnessed to enhance it.


Aligned with our goals, the project was twofold. First, we aimed to craft compelling brand messaging that positioned her as a thought leader alongside her business brand, Bossy & Blissful. 

Then, we dove into creating a comprehensive 12-month organic content marketing plan. This strategy not only targeted the debut of her two websites – one personal and one for Bossy & Blissful – but it also emphasized the fresh launch of her business-centric Instagram account and the revamp of her personal IG account.

Together, all of this was done to ensure both accounts and websites had a sharper and more defined direction.


Collaborating with Regina Lawless, we were able to successfully achieve the following:

  • Brand Launch: Officially launched the Bossy & Blissful account with a clear plan, content pillars, and direction. This clarity made it effortless to start creating and sharing content on the account.
  • Community Growth: Thanks to a tailored approach, we developed a strategy for expanding her community through in-person events, bolstered by a dedicated marketing plan for each event to enhance her online presence.
  • Personal Branding: With close attention to details of Regina’s story, we created a precise plan and direction for her personal account. This way, she was equipped with insights on what to share, where to share it, and the optimal tone. All of this came together to effectively position her as a sought-after coach and speaker.

“Cassandra and the Quirky Pineapple Team are the creative partners you need if you’re looking to solidify the messaging and content strategy for your brand. They helped me to get clear on who my company Bossy and Blissful is actually serving, how to describe my offerings in a compelling way to my target audience. Beyond that, Cassandra was a delight to work with. Her and her team are kind, responsive and go above and beyond!”

Regina Lawless , Founder of Bossy & Blissful, Coach, Speaker, and Former Head of DEI at Instagram


Leaning into The Quirky Octopus™ Framework, we worked with Regina to ensure a comprehensive strategy that resonated with her unique brand vision.

1. Branding Foundations: With Regina, we delved into the 4 Ps of personal branding and thought leadership: Personal, Personality, People, and Platform. These foundational elements were crucial in forming a strong and resonant brand identity.

2. Deep Dive Sessions: We set aside two in-depth sessions. The first session was 2 hours long and dedicated to ‘Personal & Personality’. This allowed us to dig deep into brand messaging, craft narratives, and establish the brand’s distinctive voice and tone. 

The second session, also 2 hours long, was centered around Content Marketing. During this session, we explored Regina’s target client, dissected her service offerings, and pinpointed the most effective marketing strategies for her brand.

3. Strategic Documents: Then, we worked to create Regina’s Brand Message Handbook – a 15+ page comprehensive guide that encapsulates her mission, vision, core messaging, brand values, and tone. Along with this, we also put together her Content Marketing Roadmap, a 10+ page blueprint detailing her strategy for blogs, emails, LinkedIn, Instagram, and event launches.

4. Feedback and Refinement: To ensure our strategies were aligned with Regina’s vision, we opened the floor for her insights and feedback. From there, we refined and updated what needed to be changed in order to best suit her needs.

5. Project Culmination: Our collaboration ended with a 30-minute session where we walked Regina through the final strategies, answered questions, and reinforced our shared vision. 

Once this was all said and done, Regina was officially equipped with a fully-fledged launch and action plan for the next quarter.

Ready to share the power of your message? The Quirky Pineapple Studio’s Strategy Intensives are designed to help business owners, thought leaders, and creators expand their reach, amplify their message, and create a sustainable marketing game plan.

Get in touch with Team Quirky and let’s work together to get to the core of what makes your brand stand out – all with a touch of cultural competence and inclusive marketing strategies!

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