Change MakeHERS: Spotlighting Jenn Caldwell

Why Women in Cannabis Matter

As the cannabis industry continues its rapid expansion, an increasing number of dynamic women are emerging as influential leaders within the field. These women not only shape the trajectory of their businesses but also pave the way for future generations of female leaders. At White Ash Group, we believe in celebrating the triumphs of women in the cannabis sector by highlighting their accomplishments. That's why we initiated the Change MakeHERs series – a collection of interviews and spotlight articles where women who embody strength, integrity, and hard work share their insights and advice on navigating the cannabis landscape.

JENN CALDWELL, Business Owner & Cannabis Industry Leader

In an era where impact is often found at the intersection of disruption and purpose, Jenn Caldwell is a force who meets change head-on. Her career has taken her from teaching science, to fighting for women’s health in court, to helping build Canada’s legal cannabis industry.

She didn’t follow a traditional path—she followed what mattered. And that’s what makes her a true change maker.

Jenn isn’t afraid to take on big challenges. Whether it’s standing up to powerful drug companies or helping patients find relief through medical cannabis, she leads with heart, honesty, and purpose. She believes in learning as you go, lifting others up, and staying true to your values.

In this Change MakeHER feature, Jenn shares how she’s built a career by saying yes to the unknown, supporting other women, and always staying grounded—even when things get tough.

Q: Your career spans corporate strategy, health equity, and now cannabis. How have you stayed ahead of the curve and led with impact across industries that are constantly evolving?

I’ve learned that embracing change is the price of admission to doing meaningful work in complex, fast-moving industries. From education to legal advocacy to cannabis, I’ve had to stay adaptable, curious, and open to learning. I’ve never really “planned” my career in a traditional sense—I’ve simply said yes to things that mattered and threw myself into learning everything I could.

Working in cannabis—a brand new, heavily regulated industry—meant being comfortable with ambiguity and moving forward even when the path wasn’t fully clear. I’ve always seen disruption as an opportunity. Instead of fearing change, I view it as a chance to innovate, to improve systems, and to build something better. I follow the science, stay connected to industry peers, and embrace continuous learning.

If there’s one mindset that’s carried me, it’s that no experience is ever wasted. Even the difficult ones offer something—insight, perspective, an opportunity or a connection you didn’t expect.

 I’ve also learned how critical it is to build community. I’ve grown so much through collaboration with colleagues who push me to think bigger and lead with purpose. I’ve been lucky to be surrounded by brilliant, generous colleagues along the way.

Q: Can you share your journey into health and social impact? What inspired you to pursue this work, and what has kept you committed to it over time?

My journey has been anything but traditional. I started my career as a high school science and biology teacher, which I loved. But a chance conversation at a fundraiser led me to a role at one of the largest plaintiff’s law firms in the U.S., advocating for individuals harmed by unsafe drugs and medical devices. I spent many years focused on cases involving hormone replacement therapy (HRT), fighting for women whose lives had been devastated by a drug the manufacturer knew—years earlier—could cause breast cancer. It was a two-billion-dollar industry, so they buried the studies and even paid doctors to put their names on ghostwritten articles claiming the drugs were safe.

Tens of thousands of women suffered. Many died. All because of greed.

It was devastating—but also deeply empowering. We were able to secure major settlements for many of these women and their families. Their strength, grace, and resilience in the face of betrayal and illness changed me forever. I’m so grateful I had the opportunity to work with them. They didn’t just shape my career—they shaped who I am.

Years later, I had another unexpected moment—this time at a hockey rink. A fellow hockey parent pulled me aside (after what I now realize was a very pointed line of questioning about my background!) and told me he was applying for a cannabis licence under the MMPR program. He wanted me to join his team. At the time, I didn’t know much about cannabis—aside from the negative stereotypes. I’d grown up with “this is your brain on drugs,” and honestly, I was a little offended. I remember thinking, “Why would you think I’d want to be a drug dealer?”

But he was smart—he tapped into my inner science geek. He sent me articles and studies about the medical science behind cannabis, and I quickly realized there was so much I didn’t know. I had been wrong—and I was fascinated.

I joined his team and helped build the first newly licensed cannabis facility under the MMPR. I started by creating our client care department, and from there I dove headfirst into regulatory and quality work. My science brain thrived in that space.

The cannabis industry constantly challenges me—and I thrive in that kind of environment. But what keeps me here is the impact. The patients. A woman with MS who had been in a wheelchair for months called to say she’d just walked her girls to school using a cane. The nurse of an elderly woman who had been wasting away told us she ate an entire bowl of mashed potatoes after using cannabis for the first time. A tearful wife thanked us for giving her husband a dignified death—present, aware, and free from unmanageable pain.

That kind of impact stays with you. It motivates you. It changes you. It makes you want to be better.

Q: The cannabis sector is uniquely complex—socially, politically, and operationally. What have been your most significant leadership lessons in this space?

Where do I even begin? Cannabis is a rollercoaster—constantly evolving, widely misunderstood, and full of brilliant, passionate people trying to do meaningful work while navigating intense regulation and economic instability.

One of the biggest lessons I’ve learned is that leadership starts with example. You have to walk the talk. The values you expect from your team—integrity, honesty, transparency—have to show up in your own actions first. No one is going to respect a leader they can’t trust.

I also think self-awareness and emotional intelligence are undervalued leadership tools. It’s so important to know your own strengths and weaknesses, so you can lead from a place of confidence and humility. Understanding and managing your own emotions—and being sensitive to the emotions of others—is key to navigating the high-stakes, high-pressure moments this industry regularly throws at you. I’ve made mistakes, and I’ve learned a lot from them. That kind of openness fosters a stronger team.

Another critical lesson: you don’t need to be the smartest person in the room. If you are, you’re in the wrong room. I’ve learned to surround myself with skilled, talented, thoughtful people—and most importantly, to listen to them.

I say this to my boys all the time: there’s no such thing as failure if you’re learning. You either succeed, or you grow—and both outcomes are valuable.

People are everything. Everyone you work with has something to teach you, and as a leader, it’s your job to create space for others to grow, contribute, and thrive. The relationships I’ve built in this industry are by far the best part of my work. You can’t do it alone. No one is a one-person show.

That said, there have been real challenges—particularly as a woman in a male-dominated space. I’ve been in meetings where I’ve made a point multiple times, been ignored, and then watched the room nod in agreement when a male colleague repeated what I said. It’s discouraging, yes—but it’s also fuel. I know my worth, and I keep showing up.

Work-life balance has also been a hard-won lesson. In the early years, I worked constantly. I didn’t prioritize myself or my well-being. And while I haven’t fully mastered it, I’ve learned that there will always be more work to do—but if you don’t protect your energy and your health, you won’t be able to show up for anyone else. You really can’t pour from an empty cup.

Q: As a leader, how do you actively create space for other women to rise, speak up, and drive innovation within your organization?

I’ll be honest—this is something I always feel I could be doing more of. But I do what I can, and I try to do it with intention. I mentor women on my teams and work hard to help them recognize just how talented, capable, and deserving they are. I hire women. I advocate for them. I speak on DEI panels, I attend women-led events, and I’m proud to be part of communities like Canadian Women in Cannabis and Radical Femmes that are working to move the needle.

Sometimes leadership is bold and loud—but more often, it’s quiet encouragement. It’s about making space for someone to find their voice, to take up space, and to feel seen and supported. I try to do that every day by making room for others to shine—and reminding them they deserve to.

Q: In industries that are fast-moving and often disruptive, what grounds you in your purpose and keeps you aligned with your values?

My boys are my center. They remind me of what really matters and keep me grounded—always. Nature helps, too. Whether it’s walking, hiking, or simply sitting by the ocean, being outside resets me. It brings clarity.

I also remind myself that a lot can change in a day. If things feel overwhelming now, they likely won’t feel the same next week—or even tomorrow. That perspective helps me stay steady, especially when things feel chaotic.

At my core, I live by a few simple values: honesty, trust, and authenticity. Two quotes that guide me are:

“I may be changed by what happens to me, but I refuse to be reduced by it.” – Maya Angelou

“Who you are speaks so loudly I cannot hear what you are saying.” – Ralph Waldo Emerson

Those words remind me to show up fully, kindly, and truthfully—no matter what.

Q: If you could offer one piece of advice to your younger self—or to the next generation of female leaders—what would it be, and why?

Step out of your comfort zone. Speak up. Take up space. Don’t wait to be invited - just start.

One of the most important lessons I’ve learned is that confidence isn’t optional - it’s essential. If you don’t own your strengths, it becomes easier for others to overlook them. Self-belief isn’t arrogance—it’s the foundation for impact. And it’s okay to want your contributions to be seen and valued. As women, we often give credit to everyone else and quietly downplay our own work. But visibility matters. Value matters. You matter. It’s not just okay to be strong and confident—it’s necessary.

I know you asked for one piece of advice—but I’ve got a few more:

Take ownership of your path. Don’t wait for permission.

Network and build relationships—they are the infrastructure of strategy and success.

Failure isn’t the end—it’s information.

You can’t control everything, but you can choose how you respond.

And above all—be kind. Kindness isn’t weakness. It’s a superpower. Lead with it boldly.

To the next generation of women leaders: Be unapologetically yourself. Advocate for others, but advocate for yourself too. Make space for yourself—and then hold the door open for others. Never question whether you deserve to be here—you do. Now lead.