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When Ashwin Raj took over as CEO of LeafLink, he was new to cannabis but not to the problems the industry was trying to solve. Raj came to LeafLink after leadership roles at Lyft, Amazon, Visa and ezCater, where he worked across payments, marketplaces, logistics and technology. A year into the job, he has found plenty of overlap between those businesses and cannabis, even if the industry’s history has required some adjustment.
“Looking back, I had experiences across all of those roles that applied directly — transforming a legacy business through acquisitions (in this case, the Leaf Trade and DAMA acquisitions), and bringing together an organization, technology, and multiple platforms into one unified operation,” Raj said. “At Amazon, I had to bring together several underlying payment systems into a single integrated payment system and brand, which gave me a similar playbook.”
What did not translate as easily was the expectation that a better technology would quickly win people over.
Cannabis businesses spent years operating in an illegal, tightly connected market where relationships between buyers and sellers were critical. Those habits did not disappear with legalization.
“Cannabis carries legacy stigma from operating in an illegal, tightly knit environment where trust between business partners is everything,” Raj said. “That trust had to be replicated into the platform, and it meant anything new wasn’t immediately accepted the way it would be in tech. I had to earn that trust and work closely with customers to reiterate the value of our platform, rather than assuming adoption would be immediate.”
Raj was also surprised by how much business is still conducted through older, manual processes. Orders can involve texts, emails and direct conversations, while tasks like transfer manifest creation and matching orders to inventory systems can take up hours that could otherwise be automated.
He doesn’t see that resistance as something unique to cannabis.
“Instead there’s a lot more reliance on old processes and habits, across both large and small customers. But I don’t think that’s really specific to cannabis — it’s human behavior,” Raj said. “People get comfortable with what they’re used to, and that comfort creates a false sense of speed and accomplishment. It’s on LeafLink to clearly show why a technology solution will work better than the status quo and how it helps people in their day-to-day roles.”
For smaller cannabis companies, Raj also sees a tendency to spend time and money building technology that already exists.
“My advice to small and mid-size operators: don’t spend time building your own order management or inventory management systems. Those aren’t your core competency,” Raj said. “Use what already exists, and focus on building your brand. That’s what differentiates you and makes buyers want you, and it’s what makes future combinations easier if consolidation does come your way.”
That distinction could become more important as cannabis consolidates. Raj said LeafLink is already seeing smaller operators with valuable brands absorbed by larger companies that continue operating those brands. For an independent operator, putting resources into the parts of the business that make it distinctive may prove more valuable than trying to build every function internally.
The value of consistency
Raj’s experience at Visa, Amazon and Lyft also shaped his view of trust, something he considers just as important in cannabis as it was in tech.
At Visa, trust meant knowing a payment would be processed when expected. At Amazon, it meant getting a package when it was promised. At Lyft, it meant having a car arrive when the app said it would.
“Underlying all of that is the same thing: creating confidence that the product or service will meet the customer’s expectations,” Raj said. “Cannabis is no different. It’s about the product complying with THC content requirements, packaging, and logistics. When we commit to 50 cases of product being available, it has to be available to that retailer at that time. That’s what builds trust in the system, and you have to set standards that make it inviolable for every participant in the supply chain.”
He sees similar lessons in the internal discipline required at large public companies.
“Consistency, and the internal rigor behind it,” Raj said. “As public companies, Visa, Amazon, and Lyft all had to meet market expectations, not just customer expectations, in every practice — transactions, chargebacks, delivery.”
Cannabis companies operate within a connected supply chain, meaning inconsistency at one company rarely stays contained there.
“That level of rigor and consistency in operating practices, technology, customer support, and commitments to the market is what cannabis needs to achieve — all the way from customers to partners to investors and shareholders,” Raj said.
Building around regulation
Cannabis regulation presents a different challenge, particularly for companies operating across multiple states. Raj’s background in payments has influenced how he thinks about handling that complexity.
“Technology can take a huge number of variables and simplify them into an algorithm that runs easily. That’s the beauty of it,” Raj said. “There’s no real limit to how many variables a platform can ingest, including every state’s different regulations.”
For Raj, compliance does not have to sit apart from the rest of the business as a box operators are required to check. It can be built directly into the systems they use.
“Where it becomes a competitive advantage is that satisfying those regulatory requirements becomes a core capability the business can offer its customers: you can trust us because we’ve built this in,” Raj said.
Flexibility matters just as much. Cannabis companies have to account for regulatory and tax changes alongside more traditional business variables such as pricing and supply chain disruptions. Cultivators also have agricultural uncertainty to contend with, from crop yields to changes in THC content.
“As a product leader, the question I keep asking is how you design systems and capabilities that let the business adjust rather than locking it into something too rigid to change,” Raj said.
Looking outside cannabis
After a year in the industry, Raj is less convinced that cannabis businesses need cannabis-specific answers to every problem they encounter.
“Honestly, I don’t think cannabis is fundamentally different from other industries. Its history and the legacy it evolved through are what’s different, similar to how alcohol evolved,” Raj said.
Cultivation has similarities to agricultural commodities. The industry’s regulatory requirements have parallels to pharmaceuticals. And from cultivation through the point of sale, cannabis companies are still managing a supply chain, something other industries have spent decades finding ways to make more efficient.
Raj sees standardization as one place where cannabis has room to mature.
At Visa, he led the team that developed the tokenization standard that made it possible to mask card numbers during transmission and ultimately helped enable Apple Pay and Google Pay. After developing and testing it, Visa shared the standard with the broader industry.
“As the market leader, sharing it helped grow the whole industry, and it became the universal standard that every processor and network built on and adapted,” Raj said. “I think cannabis needs that same mindset: put aside individual competitive advantage in favor of what’s right for the whole industry, and the industry will succeed as a result.”
Raj’s first year in cannabis has also reinforced a lesson that predates his arrival in the industry. New executives should spend time understanding how a business actually operates before deciding how technology should change it.
“Don’t come in with a preset idea of how the marketplace should work,” Raj said. “Marketplaces differ based on the industry and your position in the value chain, and you need to understand how you can add value.”
For tech executives entering cannabis, that may mean resisting the urge to immediately apply the practices that worked somewhere else. For cannabis operators, it means there is no reason to ignore solutions simply because they were developed somewhere else.
“Before you apply the technology, know what your customer wants, what’s working, and what isn’t. Then double down on what’s working and fix what isn’t.”
