Meet Caroline Crawford, the Founder and CEO of Cultiveight Communications, an organization dedicated to transforming how businesses approach their marketing strategies.
With more than a decade of experience in marketing and communications, Caroline noticed a recurring issue in previous roles: marketing often wasn’t given the resources or recognition it deserved within organizations. This frustration led her to create Cultiveight Communications, with the aim to integrate marketing more effectively into business strategies. By leveraging her deep understanding of marketing dynamics, Caroline has positioned herself to deliver tangible results for her clients. Ultimately, her goal is to enhance the role of marketing, helping businesses tackle it with a clear and confident approach.
We asked Caroline about the inspiration behind Cultiveight Communications’ founding, the challenges she’s faced as an entrepreneur, and her vision for the future of her company.
Tell us the story behind your company’s founding. How and why did you start working on Cultiveight Communications?
I had been in marketing and communications for 10 years before founding Cultiveight Communications. Throughout my career, I navigated various dynamics within organizations, especially within the marketing departments. One recurring theme I noticed was how marketing was often undervalued—typically receiving minimal budget and being treated as a catch-all for every organizational issue.
Starting my career was serendipitous; I landed my first internship in marketing, fell in love with bringing a brand's voice to life, and never looked back. However, the same challenges seemed to follow me in every role—limited resources, a lack of understanding from business leaders, competing priorities, and a general underappreciation of marketing's true value.
These experiences inspired me to form Cultiveight Communications. I saw a gap in how marketing was viewed by business leaders and how marketing support was delivered. My mission is to change the face of marketing by helping businesses, regardless of their limitations, carve out their place in the world. I want business leaders to prioritize marketing, understand its true value, and adopt an integrated marketing approach that goes beyond typical gimmicks. Too often, businesses take marketers at their word without asking questions, which can lead to significant issues. My goal is to bridge that gap and empower businesses to make informed decisions about their marketing strategies.
What makes Cultiveight Communications different from other similar companies in the industry?
It’s incredibly difficult for companies, especially those with limited in-house marketing resources, to find well-rounded support that truly protects and enhances their business. Many companies focus on the symptoms of their marketing challenges rather than addressing the root causes, which often leads to a never-ending cycle of frustration.
What sets us apart is our holistic approach to marketing and sales. We don’t just look at one piece of the puzzle—we examine the full spectrum. Our unique approach involves embedding ourselves within our clients' companies, allowing us to intimately understand their operations and culture. This deep integration enables us to identify gaps that might impact their marketing or sales efforts, even if it means going beyond the conventional boundaries.
Ultimately, our goal is to empower our clients to make informed decisions about their marketing strategies. We don’t just provide solutions. We ensure that our clients understand the why behind them, giving them the confidence and clarity they need to drive their business forward.
In what ways has your upbringing or past experiences contributed to how you operate as an entrepreneur?
I've moved a lot throughout my life, especially during my childhood. That constant change has made me highly adaptable to both people and situations. This adaptability has also helped me stay calm in the midst of chaos and change. This is crucial as an entrepreneur and leader.
As a business owner, I understand the weight of the responsibility I carry. People trust us to make a difference, and I don’t take that lightly. While I definitely have my moments, I believe that my ability to remain calm when others aren’t is one of my strengths. It allows me to navigate challenges with a clear head and lead my team with confidence, ensuring we deliver on our promises to our clients.
What’s been the hardest and most rewarding part of your entrepreneurial journey?
I’m not sure what I initially expected from entrepreneurship, but I now fully understand why people say that it’s not for the faint of heart. The hardest part has been continuously developing my resilience—not just in facing rejection but also in navigating conflicts, differing personalities, and opinions. It’s a constant learning curve that requires strength, adaptability, and confidence in myself and my decisions.
What was most unexpected, though, is the community I’ve cultivated along the way. I didn’t realize how much I was seeking these connections and shared experiences. This sense of community has been incredibly rewarding, providing support, inspiration, and a sense of belonging that I hadn’t anticipated when I first started this journey. It’s also helped reinforce my confidence in myself as both an entrepreneur and a leader.
Have you struggled with self doubt as an entrepreneur? How do you navigate this?
Absolutely. Self-doubt has been one of the biggest challenges I’ve faced, and overcoming it is something I’ve had to work on repeatedly. There’s no single way to navigate self-doubt, but for me, it’s been crucial to cultivate my own sense of validation and belief in myself.
One of the key ways I manage self-doubt is by operating with a high level of integrity. I know that as long as I stay true to my values and maintain that integrity, whatever is causing the doubt will eventually pass. Navigating different perceptions and subjective values can be difficult. However, I’ve learned to trust in my principles and stay grounded in what I believe is right. This approach helps me push through the moments of uncertainty and continue moving forward.
Has your definition of success evolved throughout your journey as a founder?
Definitely. I’m not sure I ever had a clear, fixed definition of success because it’s something that has evolved so much over time. In the beginning, I might have been more focused on traditional markers of success—like money, the number of clients, and other tangible metrics. But as I’ve grown in my journey, I’ve become less attached to those conventional ideas.
I’ve realized that people's definitions of success can often fuel self-doubt because you inevitably end up comparing yourself to others. However, defining success in your own way, while liberating, can also feel strange at times. It requires a shift in mindset and a willingness to embrace what truly matters to you, rather than what society dictates. For me, success has become more about fulfillment, integrity, and the impact I’m making, rather than just numbers or external validation.
How have you grown as a leader since starting Cultiveight Communications? What experiences have contributed to this growth?
As a leader, I’ve learned that it's my job to be the anchor, guide, reserve, and fuel for my team. That’s a significant responsibility. And my growth has been about embracing that responsibility more fully over time. I’ve also come to realize that if things start going awry, I have both the ability and the authority to make changes.
Building a team has been a major part of this growth. Initially, I hired people because I wanted to relieve the pressure on myself. However, I learned that if my leadership is shaky, the team will be too. I experienced this firsthand when I was so desperate for help that I neglected to lead effectively. This caused a lot of frustration for me, and likely for the team as well, even if they didn’t express it at the time. These experiences have taught me the importance of strong, steady leadership and the need to take ownership of my role in guiding the team, ensuring that I’m providing the support and direction they need to succeed.
What’s next for you and Cultiveight Communications?
Our mission is to make marketing—and the ability for people to market and grow their companies—accessible to everyone. Recently, we expanded our private consulting offerings to include an incubator program for solopreneurs at pivotal growth stages. Coming up, we’ll be releasing a platform that I believe will change the game in how businesses view their marketing and sales functions. There are even bigger and better opportunities on the horizon, which I’m incredibly excited about. But for now, I’m focused on enjoying these shifts and making the most of these exciting developments.
