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Trulieve’s Executive Director of DEI John Calloway Jr. on How Their Women-Owned Company is Leading the Way in Diversity, Equity and Inclusion in the Cannabis Industry

John Calloway Jr.

Executive Director of Diversity, Equity & Inclusion



Interview conducted by:

Bud Wayne, Editorial Executive

CEOCFO Magazine

Published – February 27, 2023

CEOCFO: Mr. Calloway, would you tell us about Trulieve, what it provides and how it reaches its customers? Do you have storefronts, a website, social pages?

Mr. Calloway: Trulieve is a leading multi-state operator cannabis company within eleven states. Trulieve has different operations within the different states based on state laws. In some states, we are wholesale. In some states, we have a retail presence.

Trulieve is poised for accelerated growth and expansion, building scale in retail and distribution in new and existing markets through its hub strategy. By providing innovative, high-quality products across its brand portfolio, Trulieve delivers optimal customer experiences and increases access to cannabis, helping patients and customers to live without limits.

CEOCFO: These are Trulieve products then?

Mr. Calloway: Yes it is Trulieve products. We do have brand partners. They can produce their products in our wholesale markets, but in vertical integration markets, we produce our brand partners' products.

CEOCFO: How long have you been with Trulieve, and what led to your leaving Walmart becoming its Executive Director of Diversity, Equity & Inclusion (DEI)?

Mr. Calloway: I have been with Trulieve for a little over a year and a half. At Trulieve, sometimes you have so much fun at work that you forget your starting date. My starting date is very special to me because it is aligned with my goddaughter, and family is important to me. My goddaughter was actually born a few days before I started.

I wanted to try a different industry. I saw that there were ways that I could be supportive within the industry with the knowledge and understanding that I had, especially from Walmart. I wanted to be able to break into this industry as it was still growing. I found Trulieve through Linkedin, and this position was something I was interested in. I spoke to my family, and they asked me if I was sure I wanted to go to a different industry. I could really see this growing, and I could appreciate that it is a women-led cannabis company.

I had seen that there were not as many minority leaders within the cannabis industry, and I wanted to be able to see that change. It is one of the things I am most passionate about. I want to see the cannabis industry diversify to be a place women, minorities, working parents, and everybody feels that they can be leaders within this environment. Education is really big for me, and I am able to educate within the role that I am in.

CEOCFO: Were you involved with DEI prior to coming to Trulieve?

Mr. Calloway: I have always been involved. From Walmart, you are able to do things from store to store. I was doing more store-to-store activities and working with my regional teams to ensure that we diversified our store and our staff while developing programs to ensure that we have folks that match the store in the community.

I became most interested in this work after meeting Walmart's former Chief Diversity Officer Ben-Saba Hasan. I had an opportunity to speak to him and understand where his passion came from, and I realized that his passion heavily aligned. My heart is in the community and the diversity of thought. Those are things that he was big on and things that he proliferated across the Walmart organization and throughout my career.

When I got to Trulieve, I had the opportunity to bring the concept of Employee Resource Groups to the organization. These groups were officially established last year. I have been able to see the impact that the ERGs have had on the organization so far. Prior to this role, I was Director of Performance Management, which helped me focus on diversifying the ranks throughout the organization.

CEOCFO: Would you tell us about your role as Executive Director of DEI?

Mr. Calloway: As the Executive Director of DEI, I oversee and manage the diversity, equity and inclusion within the organization as well as corporate social responsibility, which includes all our philanthropic giving along with our volunteerism and national partnerships. I also oversee community engagement and the actions we take in the community and supplier diversity within the organization.

CEOCFO: Trulieve has its own history of encouraging DEI. Would you tell us about the company’s commitment to Diversity, Equity and Inclusion and social responsibility?

Mr. Calloway: Our company is one of the only multistate operator cannabis organizations that is woman-led. Our CEO is passionate about social justice within the cannabis industry. We understand that the cannabis industry was impacted by the war on drugs. We understand that black and brown communities suffered some of the greatest opportunities from the war on drugs. Our CEO embraces and understands that, so she is passionate about driving diversity not only in the organization but also in communities to give back to those that were most impacted.

My focus is to engage at the local, state and national level to champion our core focuses: minorities, women, veterans, working parents and caregivers, and to support tangible positive change through community education, volunteerism and through partnerships and sponsorships. We also advocate for social justice reform, which is something that our CEO is also passionate about.

She wants to see the release of those incarcerated because of cannabis. She is also a massive supporter of expungement; we are pushing this nationally. Along with expungements, want to educate people. Oftentimes, when a state legalizes, there may be some automatic expungements; however, not everyone’s records actually get expunged and sealed. As a result, we work with different organizations that educate and help folks to get their records expunged. We do a lot of authentic work with authentic organizations.

CEOCFO: So you are involved with so many different aspects of the community, as well as running the company!

Mr. Calloway: I think that is what helps us because I try to tell people that some of the strongest and most impactful groups that you want to encounter are those that can be allies for you. It is best for us to spread the message far and wide across the organization as well as in our communities. We need the allies, and they are the ones that can truly help to sponsor and push. You want to educate the allies, which is one of the reasons that I am so excited to be in a position where I can influence. An example of this would be our efforts for Martin Luther King Jr. Day where we brought team together across the country.

We had the honor to spread our MLK efforts across our different states, supporting social justice across the country. We attended events in Jacksonville, St. Pete, Tampa, Atlanta, Phoenix, Boston, and Philadelphia. We wanted to make sure that even our associates understood this is a day of honor and service and understood the “why” behind the honoring and service.

CEOCFO: Were the MLK events part of Black History Month?

Mr. Calloway: These were just in honor of MLK. MLK has always been one of my heroes and for everything he stood for. I just get goosebumps when I think about the impact his legacy and his family continue to have. We wanted to do something beyond giving back while educating our own employees. We participated in days of service and participated in walks. We wanted the associates to have organic celebrations and to be a part of something while continuing to educate. The more we educate them, the more they educate others. Diversity goes beyond our walls, and every seed we can plant. That is how we change communities.  

Trulieve Held Fireside Chat with Civil Rights Leader 

Ambassador Andrew Young in Honor of Black History Month

See more Photos Below

CEOCFO: February is Black History Month. Would you tell us some of the things and events you are doing and involved with that help in celebrating such an important time of recognition?

Mr. Calloway: We took a multifaceted approach to Black History Month. Every time I do programs, I usually break down programming into a national focus and then a state-based focus. We have oversight of the community engagement groups. This February, we are partnering with Project Goo, which stands for Giving Opportunities to Others. We will be partnering with Projects Goo to host a food drive in Tallahassee during the FAMU Harambee Festival on February 25, which is expected to bring in thousands. However, we cannot just stop there. The work needs to continue beyond Black History Month if we want to give back to these communities. We worked with Project Goo to kick off their food programs in February. Over the course of the next few months, we will be going into Baltimore, Philadelphia, and Boston to continue this work. We also hosted a Fireside Chat highlighting the success of the first HBCU Ambassador Cohort, which created actionable change in their community with the Students for Sensible Drug Policy (SSDP). We are conducting some community consortiums with the Sickle Cell Foundation. We are working with the Sickle Cell Community Consortium on educational webinars to teach people about sickle cell and the power of the plant. We also say the work does not stop there. In Arizona, we are partnering with the Black Philanthropic Initiative and participating in the Let’s Make History Together gala. We have quite a bit going on, and that is just external.

Internally, we focus on black excellence past, present and future. Week by week, we followed the National Museum of African American History and have been sharing these resources with our associates. By sharing this information, they have been able to reflect on the topics to understand more about black history. It is interesting since it takes a different approach over, and there is even a section for children to understand more about Black History Month.

As a next step, we wanted to have some fun in the organization. Our African American ERG (Employee Resource Group) has been leading a lot of these efforts and hosts weekly trivia for us. The last key point for our internal employees is The Calm App we provide as a free resource for our associates. We have been able to focus the employees around different stories, meditations and even music that features black artists and mindfulness experts for them to explore.

CEOCFO: What were some of the accomplishments in DEI for Trulieve in 2022 overall, and already in 2023?

Mr. Calloway: Throughout 2022, we actually conducted 445 events last year that focus on diversity, social justice and community. This is great for the team. Our associates participated in all of those events. Last year, we put a major focus on our on-the-ground support. We wanted to be intentional with the programming and our efforts to ensure the greatest impact in those communities we serve. In 2022, we kicked off our Employee Resource Group program. It has been very well received by the associates, and we are able to create an authentic community.

When you look at the terminology of inclusion and diversity, belonging always comes to mind. Trulieve’s Employee Resource Groups help the employees and associates from all levels. They are all supported by an executive sponsor, the leadership includes hourly associates. It helps to create a sense of belonging with organic conversations to learn from those who may be in the same position or a different part of the business. We all have different experiences, and now, employees can share their experiences and help each other. It even creates more of that organic mentorship, which has been very exciting and drives engagement.

CEOCFO: Would you tell us about the black community’s involvement in medical cannabis, both as consumers and also from a business standpoint? Is the black community accepting of it as a medicinal product, or is it still a bit leery?

Mr. Calloway: While I can’t speak on behalf of the entire black community, I have encountered that many black Americans grew up with the stigma that cannabis is bad without any benefits, because of the war on drugs. It takes the education to really teach people about the positive points and the medicinal backing of cannabis. I feel we are starting to see a shift, and I am starting to see more black interest–by leaders that want to join the cannabis industry or individuals who want to open their own dispensaries or have their own products on the shelves. It is not enough to remove convictions and expungements alone. We have to focus on equity in the cannabis industry, and I am starting to see many black Americans do this by creating businesses themselves and helping others to create their businesses.

For Women’s History Month in March, we are partnering with Women Grow. As a part of our Supplier Diversity Summit with Women Grow, we are going to educate women-owned businesses on the certification process and prepare them to make pitches to different cannabis organizations and companies. These women will be able to capitalize on the finances within the industry. As an organization, we are not just focused on driving equity within Truileve. We want these women to be able to capitalize on the full financial opportunity within the industry.

Even in my own company, we have Trulieve Georgia President Dr. Lisa Pinkney. She is an accomplished doctor, scholar and a phenomenal, influential leader who started her career working within the federal government and transitioned to cannabis. She is an example of someone who didn’t start her career in this arena and is making a difference. With her platform, she is helping and encouraging others to propel other black-owned businesses and other minority groups.

Someone else very important is Roland “Champ” Bailey Jr., the NFL Hall of Famer and Trulieve Georgia’s Chief Diversity Officer. He understands that there is a lot more that needs to be done in the cannabis industry and joined Trulieve to invest back into Georgia communities and community partnerships.

It is a change, and we are still on the ground floor. However, we are starting to see that forward movement. In February, we have the honor and the privilege to do a fireside chat with Ambassador Andrew Young.

CEOCFO: In closing, what separates Trulieve from other medical cannabis companies?

Mr. Calloway: What separates Trulieve is our authentic desire to truly propel Diversity, Equity and Inclusion and community impact. That is what attracted me to the organization. Also, the autonomy and ability that I have as a DEI practitioner to be able to push these efforts through my organization while pushing this same message through the communities by which we serve.

Our entire C-Suite is involved in DEI and focused on community. I believe the commitment from our C-Suite and CEO along with the autonomy they have granted me, my passion, and my team, is what sets us apart. I have one of the best teams in the industry, and I could not be more happy and more proud of my team.

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Trulieve Held Fireside Chat with Civil Rights Leader 

Ambassador Andrew Young in Honor of Black History Month

Young shared stories, insight and advice to the next generation of community leaders

Ambassador Andrew Young

“I want to see the cannabis industry diversify to be a place women, minorities, working parents, and everybody feels that they can be leaders within this environment.”
John Calloway Jr.






Trulieve Held Fireside Chat with Civil Rights Leader 

Ambassador Andrew Young in Honor of Black History Month

Young shared stories, insight and advice to the next generation of community leaders

See Fireside Chat Photos Below

Trulieve Held Fireside Chat with Civil Rights Leader 

Ambassador Andrew Young in Honor of Black History Month