Akerna CEO Jessica Billingsley on jumping from a career in tech to becoming the first woman to lead a cannabis company to trade on the Nasdaq

• Jessica Billingsley has spent 12 years in cannabis and took her company Akerna public in 2019.
• She talked about her career, how Akerna got started and grew, and what going public entailed.
• Billingsley, passionate about encouraging more women in cannabis and tech, recently launched Akerna’s One Woman Challenge.
• Visit Insider’s homepage for more stories.

For Jessica Billingsley, the Colorado-based CEO and chairman of the board of cannabis enterprise software company Akerna, setting the bar, then raising it, has been a regular practice in her 12 years in cannabis. This philosophy has helped her become an early market entrant who continues to serve as a leader in the cannabis space.

In 2019, her company MJ Freeway merged with special purpose acquisition company (SPAC) MTech Acquisition Corp. The merger created the brand Akerna, which now trades on the New York Stock Exchange under the KERN symbol. Billingsley was named CEO upon the deal’s completion, making Akerna the first woman-led cannabis tech company to trade on the Nasdaq.

Since going public, some of Akerna’s strategic acquisitions include the purchase of cultivation compliance brand Trellis in April 2020 and Canadian seed-to-sale platform Ample Organics in July. To date, Akerna has an established presence in 14 countries, offering six products across the supply chain. In November, the company reported year-over-year revenue growth of 40%.

Billingsley’s initial foray into cannabis began in 2008. Then heading up a tech services firm, she was invited to invest in one of Colorado’s first licensed operators. Deeming the venture to be worthwhile, Billingsley invested. 

However, it was a family member suffering from a demyelinating illness (a condition that results in damage to the protective covering, or myelin sheath, that surrounds nerve fibers in your brain, optic nerves, and spinal cord) that served as the primary driver for the move. She saw promising medical reports backing marijuana’s potential in treating those like her family member. Her interest in the market only grew that first year, and she said she credits meetings with prominent figures like cannabis activist and entrepreneur Montel Williams as early influential moments.

“Interestingly, many, many, many people who got started very early on had some health and/or wellness reason for pursuing cannabis,” Billingsley said. 

Kickstarting the seed-to-sale tracking sector

A year of investing prompted Billingsley to dive deeper into the cannabis space. She noted that several crucial data points in the industry’s supply chain went untracked — specifically, the plant’s genetic makeup, leaving information gaps across the marketplace. 

Seeking to provide a comprehensive analysis of the plant, Billingsley launched MJ Freeway in 2010, providing tracking from cultivation to sale. The company’s creation lit a fire under the now booming seed-to-sale tracking sector — which now boasts a bevy of industry players, including Flowhub, Viridian Sciences, BioTrack, and Canix, the winner of the 2020 TechCrunch Startup Battlefield competition.

The compliance software company grew with an eye on marijuana’s future. Continued innovation and evolution brought about rapid growth during the initial years, including a 205% growth rate between 2012 and 2015. The company generated $2.5 million in revenue during the same period. In 2015, the company capped the year off by closing an $8 million series B fundraising round. Led by prominent American investor Roger McNamee, the round funded the development of MJ Freeway’s enterprise B2B business product, MJ Platform.

Knowing the cannabis space would want enterprise resource planning (ERP) software, just like any other market, allowed the company to think beyond its early stages. 

“Even at the time, we saw the coming future — that cannabis would scale, cannabis would begin to truly span different markets, jurisdictions, governments with different compliance requirements, and ultimately, international currency conversion,” Billingsley said.  

Going public 

Several more years of growth led Billingsley and MJ Freeway to a point no woman had yet been in cannabis: listing on the Nasdaq. 

The deal’s completion was no easy task, with the companies dedicating over six months of additional time to address any potential legal hurdles they might encounter. Part of the process included documenting any small decision the company made, knowing that a cannabis brand would be under more scrutiny than other markets. 

The decision paid off, as Akerna eventually received its approval — something Billingsley wasn’t assured using other public listing methods. “If we had attempted an IPO or an uplist or something along those lines, it is possible just to be ignored forever,” she said. 

Making history wasn’t the direct goal when starting out, she added. That said, an exit was always an ultimate purpose. Going public ultimately presented itself first, which allowed the company to conduct “strategic M&A,” Billingsley said, and once again look toward the future, this time focusing on the global market while preparing for an eventual end to conflicting US federal and state cannabis laws. Billingsley said the goal is to “firmly position us as the only scale technology provider.”

Promoting women in tech and cannabis

Billingsley recalled that she often was the only woman in the room in the early days. Since then, things haven’t changed all that much for women in cannabis or tech.

Akerna’s One Woman Challenge, launched by Billingsley in 2018 to promote inclusive hiring and keep women in tech roles beyond their mid-career, believes that supporting women doesn’t always have to be on a grand scale. Leaders of business of any gender are encouraged to get involved through small but significant efforts, which can include getting coffee to discuss work or setting more dedicated meeting times with interested individuals each month — practices Billingsley continues today. She reported that of Akerna’s five executive team members, two are women and one is a person of color.

While she believes that inclusion is the right thing to do for equality, Billingsley suggested highlighting ROI when advocating with business leaders. “By every measure, diversity is good for business,” she said. 

Remaining centered and creative in an increasingly demanding space

Billingsley doesn’t believe in work-life balance, joking that colleagues would say she works all the time. However, she does see the value in having time spent away from work.

“I don’t know about you, but I have never once gotten my best idea during a whiteboard session,” Billingsley said, adding that her best ideas tend to come after rock climbing, yoga, or even a shower. 

She credits the approach to her mother, a professor of nursing with a particular interest in consciousness. She recalled her mother’s lifelong advice to think of a problem before sleeping so that her subconscious could come up with a solution overnight.

“It’s amazing how true that can be,” Billingsley said. She added, “I think we need time away from work, and we need to acknowledge that work is not only in the office.” 

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