That's COO

Amy Troutmiller is one of those rare people who has been both fortunate and intelligent enough to build a career that closely aligns with her passion. In Amy’s case, her passion is for hospitality, specifically the world of food and beverage.

Amy discovered this passion more or less by accident. As she put it “I was doing, you know, hospitality and wine jobs on the side and was like, wait, I actually really enjoy this.” Leaning into that insight, Amy moved to South Beach shortly after college, where she enjoyed working in restaurants, bars and clubs.

After a few years of that work, she realized that there was a potential to turn it into a rewarding career and eventually relocated to Chicago, where she started on the management track at Kimpton.

Throughout this time, Amy’s passion for the the world of wine and spirits was readily apparent. At a young age she attained the prestigious sommelier certification, speaking to her depth of understanding of wine. She was also a founding member of an organization called Ladies United for the Preservation of Endangered Cocktails.

My big takeaway from listening to Amy talk about this part of her career is that she was smart enough to lean in to what she really cared about, which allowed her to excel in her future jobs.

After 3 years at Kimpton she took a job with Ritz Carlton, where she eventually became the Senior Manager for Beverage Development. Throughout this phase of her career, Amy was constantly looking for opportunities to learn and grow.

“What benefited me the most and allowed me to move up pretty quickly at different phases of my career was looking for opportunities, learning things that I didn’t know. Approaching people and saying, ‘Hey, I see you’re really working on how to optimize this software, can I sit in with you, or would you mind showing that to me?’ Just being willing to both put yourself out there but also ask for opportunities to learn things that you don’t know. And, I think through that, you sometimes find things that you’re good at that you didn’t know you were good at or that you’re interested in that you didn’t know you were interested in.”

That spirit of learning naturally lead Amy to entrepreneurship and eventually she founded several businesses, including a consulting firm. It was her work in the consulting space that led to her current role as COO of Really Good Boxed Wine.

The founder of the company was referred to Amy for her expertise in this complex and heavily regulated industry. “And, as soon as he started telling me what he was building, I immediately was like, this is something I want and need to be part of because it’s so needed.”

The opportunity that was so readily apparent to Amy, by virtue of her years of experience, was to reimagine what boxed wine could be for American consumers. Historically boxed wine in the U.S. had been cheap and bad, but Amy knew it didn’t have to be that way. In fact, because the one-way valve in a box of wine doesn’t allow air in, boxed wine lasts for up to 6 weeks after opening. That means that customers can enjoy one glass a night instead of having to worry about finishing an open bottle.

“Those people find us and they’re overjoyed that they have this ability. Or people who have really embraced drinking and moderation in their life and they were buying really crappy stuff because if they had to dump half a bottle they didn’t feel bad and now, because our product stays fresh for 6 weeks, they’re like, ‘I can have a glass once or twice a week.’”

Of course, reinventing an existing category never comes easy. One significant challenge was finding facilities that could create the box in bag product that the business required. Another challenge, perhaps more pleasant, was forecasting for what turned out to be explosive growth.

“In Q4 2023 we had 417% growth over Q422, so we had found efficiencies in our customer acquisition costs and things like that.”

When I asked how they could possibly have forecast such rapid growth, Amy’s answer was simple. “Optimism.”

Really Good Boxed Wine launched nationally in 2022 and is currently available for purchase online in the 45 states (plus Washington DC) where that is legally possible. They also have a nascent but growing wholesale business, which is a great channel for introducing new consumers to the brand and the product.

In reflecting on what it takes to succeed in the COO role in a growth stage startup, Amy emphasizes the flexibility and dynamism that it requires. “I think that it’s probably one of the more well-rounded roles in any organization. You know, it doesn’t have a one-size-fits-all description. You have to have financial competency, you have to have operational competency, you have to have people competency. It kind of encompasses so many different skill sets.”