We caught up with the brilliant and insightful Courtney Greenwood a few weeks ago and have shared our conversation below.

Courtney , thanks for taking the time to share your stories with us today Let’s start with the story of your mission. What should we know?

At Greenwood Marketing Collective, our mission is to bring marketing clarity, confidence, and strategy to organizations doing meaningful work—whether that’s in healthcare, health tech, ed tech, or the nonprofit space. But the mission isn’t just a business angle. It’s deeply personal.

I started my career with a pull toward healthcare—not as a clinician, but as someone who wanted to make a difference behind the scenes. Through an internship at Hartford Healthcare in Connecticut, I discovered how marketing, community engagement, and business development could directly support better patient outcomes. It clicked. My parents both worked work there too, so I saw firsthand the impact of their work, and I knew I wanted to be part of that ecosystem in my own way.

Later, as a grant writer for a psychiatric and substance abuse hospital, I had the opportunity to directly influence funding for patient programs. That experience solidified my belief that strategy and storytelling can be tools for good. Greenwood Marketing Collective was born out of that belief—designed to be a modern, strategic partner for organizations that are doing mission-aligned work but need help cutting through the noise.

This work matters to me because the outcomes matter. Whether it’s making healthcare technology easier to adopt, helping a nonprofit tell its story more effectively, or guiding a founder through a rebrand that better reflects their values—our mission is to amplify the people doing the real work. It’s personal. And it’s purposeful.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I am the founder of Greenwood Marketing Collective, a New England native (part-time Southerner), ocean-lover, and lifelong believer that good marketing should make sense and make a difference. Starting the business is realizing a life-long dream of becoming a founder and entrepreneur.

I didn’t take the straightest path into marketing, but I’ve always followed the thread of purpose. I started in healthcare because I wanted to support patients—not from the bedside, but from behind the scenes. My early work as a grant writer for a psychiatric hospital, paired with an undergrad internship experience in healthcare business development, opened my eyes to how powerful marketing, community engagement, and clear messaging could be in driving real outcomes in healthcare. My parents both worked in healthcare too, so I witnessed firsthand the ripple effect that systems, communication, and access can have on people’s lives.

Greenwood Marketing Collective was born from that purpose—with a mission to support healthcare innovators, mission-driven companies, educators, nonprofit changemakers and beyond. We’re a boutique consultancy that builds bold, strategic, and story-driven go-to-market plans, messaging frameworks, rebrands, and campaigns – just to name a few. In short, we help good people doing great work find their voice, stand out in a noisy market, and grow with confidence.

The clients we work with are often stretched thin, deep in their zone of genius, and just need someone to make their vision make sense—externally and internally. We solve problems like unclear positioning, disjointed messaging, launches without strategy, and growth plans with no map. Whether it’s a health tech platform entering the market, a nonprofit needing to clarify its value, or a founder rebranding their business—we come in with clarity, confidence, and a solid plan.

What sets us apart? We blend high-level strategy with genuine heart. I bring over 15 years of experience spanning product marketing, funds development, community relations, marketing, and strategic consulting—but I also bring a deep understanding of how mission and messaging intersect. We don’t do cookie-cutter. We build brands that feel like you, but sharper, clearer, and ready to scale.

What I’m most proud of is that my work doesn’t just sound good or look good—it has impact. We’ve helped clients bring innovative products to market, improve adoption of life-changing tech, boost community impact, and finally feel seen and heard in their market.

At the end of the day, I want people to know: we’re here to help you grow—authentically, boldly, and on your terms. And yes, we’ll probably laugh and drink a lot of coffee along the way.

Have any books or other resources had a big impact on you?

Absolutely. One book that profoundly influenced my entrepreneurial philosophy is Synchronicity: The Inner Path of Leadership by Joseph Jaworski. I first encountered this book in my mid-20s, a period marked by intense anxiety about the future. Balancing full-time work with business school, I was consumed by fears that I was “running out of time” and that I might never make the meaningful impact I aspired to. It was during this tumultuous time that a dear family friend and mentor, Jeffrey Roule, gifted me this book, which became a turning point in my life.

Jaworski’s narrative is a deeply personal exploration of leadership, emphasizing the importance of inner transformation and the interconnectedness of events and people in our lives. He introduces the concept of “synchronicity,” inspired by Carl Jung, describing it as meaningful coincidences that guide us toward our destiny when we are open and committed to our path. This perspective helped me reframe my fears, shifting from a mindset of scarcity and urgency to one of trust in the unfolding journey of life.

Now, as a seasoned professional in my early 40s, I can attest to the truth of Jaworski’s insights. Time and again, I’ve witnessed how seemingly random encounters and experiences have converged to shape my personal and professional path in meaningful ways. This understanding has not only enriched my own journey but also empowered me to mentor others, helping them recognize and embrace the synchronicities in their lives.

I learned that leadership is less about control and more about presence, authenticity, and openness to the possibilities that life presents. It’s a philosophy that continues to guide me and one that I strive to embody in my work and relationships.

Any fun sales or marketing stories?

One of my favorite and most meaningful marketing stories comes from my time working with Greenway Health, a well-established EHR company that was, frankly, losing customer trust. Their software had fallen behind – users were frustrated with outdated UI/UX, slow innovation, and inconsistent release cycles. Churn was rising, sales were slowing, and the market saw them as a “legacy” player instead of a modern healthcare partner.

When I stepped in, the stakes were high. We couldn’t just put a fresh coat of paint on the brand—we needed to rebuild from the inside out. The risk? Instead of leading with marketing fluff or a surface-level product push, I took a listening-first approach that delayed outward action. I interviewed every customer-facing team – sales, support, implementation—and even sat down with some of the customers themselves. I wanted to understand exactly where the trust was broken and what people really needed to hear and feel to believe in Greenway again.

From that work, I built the go-to-market strategy for their two-year innovation roadmap. But this wasn’t just a product launch—it was a story of redemption. We created a campaign rooted in transparency, outlining not only what Greenway was building next, but why, how often, and with whom. We focused on themes like customer-led innovation, smoother workflows, and making the daily experience of using the platform better. We packaged the roadmap into digestible, confidence-building touchpoints: from sales enablement materials to customer webinars (which I led, and some had over 800 physician attendees!) to field-ready narratives.

The impact? We started to see a shift. Sales teams had a compelling, trust-centered story to bring back to skeptical prospects, and a client-centric roadmap to share. Customers who were considering leaving decided to stay—because they felt heard since we delivered on requests. And most importantly, the internal teams felt aligned and re-energized around a shared vision of progress.

That project reminded me that marketing isn’t just about splashy headlines or clever campaigns. Sometimes, it’s about listening deeply, telling the hard truth, and having the courage to rebuild trust one conversation at a time.

Contact Info:

• Website: https://www.greenwoodmarketingcollective.com
• Instagram: @greenwoodmarketingcollective.com
• Linkedin: https://www.linkedin.com/in/courtneygreenwood

Image Credits

My husband Travis Haynie and my friend & fellow marketer Taylor Marie Ion.