Drew Cesario, SVP of Sales & Marketing for Jaunty – Interview Series

Given the many similarities between the alcohol and cannabis sectors, as each offers a product mostly for adults over 21 in the United States, there is an increasing number of professional transitions to the latter. One such professional who has made this transition, previously working for alcohol giants and distributors such as Southern Wine & Spirits, is Drew Cesario, SVP of Sales & Marketing for Jaunty,” a New York cannabis producer specializing in oil-based products, including the state’s top-selling vape brand.

So what topics did you primarily study while attending Florida State University? How would you say that studying those very vast topics prepared you for a career in cannabis and AI technology?

I double-majored in finance and real estate. At the time, that felt like the most entrepreneurial path I could put together. While it gave me a foundation in numbers and helped me stay curious about building things, it didn’t directly prepare me for cannabis. Cannabis, and especially cannabis industry operations combined with AI, requires curiosity, creativity, and the willingness to solve problems without a clear roadmap. My undergraduate education didn’t address this directly, but the curiosity it instilled has carried me forward.

What student organizations were you in during your attendance at FSU, and how did those organizations benefit your career and employment opportunities?

I joined a fraternity, which at first might not seem professionally useful. But as social chair, I managed a $40,000 budget to plan formals, charity events, and fundraisers. That taught me event planning, budgeting, and people management early on. I also joined a leadership program my freshman year, which gave me training and exposure to guest speakers. Both experiences shaped my network, as I’m fortunate to have lifelong friendships that still play a big role in my life today. Relationships are everything in business, especially in cannabis.

What first caught your professional attention about working in the alcohol industry? Did you ever anticipate working in that industry while studying at FSU?

I didn’t anticipate working in the alcohol industry at all while in college. But although I didn’t study it, I had an uncle who was an executive at The Wine Group, overseeing brands in 20-plus states. I admired his work-life balance. He worked from home, lived on a golf course, and was present with his family. That lifestyle was attractive, and there’s also a certain romanticism about wine. So I gravitated toward it.

How did your job duties change depending on the alcohol brand you were working with? Did the higher price of some brands require different sales and marketing duties than others?

My career in wine and spirits covered the full spectrum, from selling high-volume wines like Franzia to luxury spirits like 30-year-old Scotch. At The Wine Group – my first job in the beverage industry – I worked on mass brands. Later, at Pernod Ricard, I was in their prestige division, selling vintage champagne and premium spirits to high-end hotels and restaurants. Selling sangria in New York dive bars is very different from building luxury champagne programs at the Beverly Hills Hotel. That range taught me how different buyers think, why exclusivity matters as much as price, and how status plays into luxury sales.

What inspired you to make the career transition from alcohol to cannabis and cannabis technology? Did you have any initial professional concerns about being associated with cannabis?

I was early to California’s adult-use cannabis market, and yes, there was stigma. My girlfriend at the time even asked me not to join because of how her family viewed cannabis. For me, it was both running away and running toward something: away from the heavy drinking culture of alcohol, and toward an industry that felt more health-centered, liberating, and sustainable with regards to lifestyle in the long term.

What are your regular duties as SVP of Sales & Marketing for Jaunty, and how do you ensure the brand’s success amid a young but constantly evolving industry?

My role at Jaunty is to develop and guide our go-to-market strategy, ensure we anticipate market shifts, and maintain our product market fit.  I depend on our very talented Director of Marketing, Carol Tyson, to manage trade marketing, while I focus on sales and sales operations. We invest a lot in business intelligence to support our sales team so they know where to focus their time and attention. We lean on a lot of data to determine gaps in our distribution by product line to make it easy for our sales team to sell the right SKUs to the right stores. This collective work usually results in high sales velocity, balancing the effectiveness of our sales push with marketing’s pull-through. 

 As someone who’s worked in sales and marketing for both alcohol and cannabis brands, what are some similarities between successful sales and marketing strategies for the two industries?

There are definitely several similarities. The broad strokes trade marketing playbook is almost identical, though the details differ. Both industries are highly regulated, are B2B2C in structure, and both industries are big on relationships. Even the way people buy has crossover: people shop for flower in the same way they do wine – primarily by strain and varietal, respectively. We see similarities in people purchasing liquor much like they do oil in cannabis – they’re influenced by the brand more than by specific strains. At Jaunty, focusing on oils has been important for a lot of reasons, this being one. 

Since you also have quite a bit of experience in the tech industry, what are some notable ways that AI could change the operations of the cannabis industry? What regular duties could AI fulfill and possibly eventually turn obsolete?

Cannabis is a bit of a laggard when it comes to tech adoption. Frontline sales roles in cannabis are under zero threat like the SDRs are at software companies. The real impact I see will be across operations. I could see AI supporting and eventually taking over revenue operations via preventing out-of-stocks, improving capital efficiency, and all connected to ERP systems, ensuring all manual tasks associated with forecasting, ordering, and paying of non-cannabis inputs get taken care of effortlessly. Over time, that will squeeze out more profitability. There are also AI-adjacent tools in advertising, like ad budget balancing for better target audience spending that will emerge and improve, but that’s more algorithmic than truly AI-driven.

Particularly within cannabis, what are some ways that brands can successfully market their products while staying within the strict advertising guidelines of most major digital platforms?

Impactful strategic partnerships at ad service companies are extremely valuable to guide, deploy and manage cannabis advertising. At Jaunty we work with vendors like Surfside and Dutchie, who can handle targeted advertising both in-store and online. Techniques like geofencing help us serve ads to consumers who’ve visited a store, while staying compliant. Beyond digital, we invest heavily in trade and field marketing, which involves building strong retailer relationships and influencing consumers in the store before purchase. At the end of the day, it still comes down to grassroots, face-to-face connections with budtenders, store managers and buyers. Work with them to pollinate the market alongside you. 

If cannabis is rescheduled to Schedule III, how would that change the duties of both your job and the operations of Jaunty? 

Schedule III is a tax cut, not a fix. Consumers may see lower prices, but variety will shrink as cheap capital flows to the biggest players. If we aren’t careful, New York shelves drift toward sameness fueled by MSOs.

My job shifts from tax survival to price discipline and scale. I would work with finance to re-forecast the P&L, lock a pricing architecture that protects contribution margin, and set promo guardrails so we don’t give away the tax delta. Operations would have to get crisper with all the additional MSO competition since the market will get louder and cheaper. Our edge would be our focus: defending the shelf, maintaining high sales velocity, and investing where velocity compounds.

Thank you for joining us, Drew! For more information on Jaunty, please visit its website.