We are Building a Team!
At Tipsy Teacher, we blend fun with purpose. Whether you’re closing deals, running events, creating content, or keeping our operations tight, you’ll be part of a team that works hard, laughs harder, and makes a real difference for teachers across the country.
Sound like your kind of chaos? Join the mission.
Event captain
Love people, wine, and good vibes? You might be our next Event Captain.
As the face of Tipsy Teacher at festivals, markets, and events, you will bring the energy, pour the wine, and share our mission of funding underfunded classrooms. You will lead event setups, engage customers, and make sure everyone leaves smiling.
You must be local to Maryland and available on weekends.
If you are outgoing, reliable, and love turning strangers into fans, we want you on the team.
Wholesale Closer
Tipsy Teacher Wine is looking for a bold, outgoing Closer to help us grow our distributor network and get our wines on more shelves, in more glasses, and funding more classrooms.
You’ll connect with retailers, distributors, and wine shops who already love what we stand for — your job? Seal the deal and expand the Tipsy Teacher movement nationwide.
If you’ve got that perfect mix of charm, hustle, and heart — and you’re fired up about selling wine that gives back to education — let’s talk.
Local Content Creator (MD)
If you live for storytelling, viral moments, and capturing the energy of real people having a great time — keep reading.
Tipsy Teacher Wine is looking for a Creator who’s local to Maryland, available on weekends, and ready to dive headfirst into our events, camera in hand. You’ll be gathering content, filming the fun, and helping shape the story behind a brand that’s funding underfunded classrooms, one glass at a time.
You should be social media savvy, obsessed with making each video better than the last, and hungry to grow with a brand that’s building something special — including a brand-new podcast.
If you’ve got the personality, creativity, and drive to make people laugh, care, and hit “follow”… we want to meet you.
Operator
We’ve got the mission. The momentum. The brand.
Now we need someone who can make the machine run smoother, faster, and smarter.
Tipsy Teacher Wine is looking for a hands-on Operator — someone who thrives on systems, logistics, and getting things done. You’ll help keep our wholesale, events, and eCommerce operations running like clockwork while freeing up the team to focus on growth.
This isn’t a desk job. It’s boots on the ground, sleeves rolled up, solving problems before anyone else even sees them.
You should be: Local to Maryland, Organized, resourceful, and tech-savvy, Hungry to grow with a purpose-driven brand that’s funding classrooms across the country
If you love building structure in the chaos and making things work better every day — let’s talk.