Co-founded by Brittany, who is still in the classroom today.
Careers
Careers at Tipsy Teacher
Come work with a teacher-founded winery
We are a small Maryland team that makes small-batch wine, shows up at festivals nearly every weekend, and funds a real classroom every month. We are hiring for two roles right now.
Now Hiring
Event Captain
$30 to $40 an hour, tips included
That is what our captains actually average. Base pay is hourly, tips are shared by hours worked, and you earn commission on every wine club membership you sign up. Tips vary by event, so treat that range as a real average rather than a guarantee.
Teachers make our best captains. You already know how to hold a room, explain something clearly, and stay warm with strangers for eight hours straight. That is the entire job. Former teachers, current teachers looking for weekend income, and anyone in retail or hospitality who likes people all do well here.
Event Captains are the face of Tipsy Teacher. You run our booth at festivals, markets, and wine events across Maryland: pouring tastings, telling the story behind the labels, selling wine, and signing up wine club members.
We would especially love someone in or near Frederick County, since we have a growing number of events in Thurmont, Frederick, and western Maryland. That said, if you are anywhere in Maryland and this sounds like you, apply anyway.
What a typical event looks like
- A Saturday or Sunday, usually 9am to 6pm including setup and breakdown
- You pick up wine and booth gear, set up the tent and table, and brief any volunteers
- You pour tastings, talk to a few hundred people, and sell
- You pack up, count wine and cash, and send a short report the same day
- Most captains work 2 to 4 events a month, heaviest in spring and fall
What we are looking for
- 21 or older, since you will be serving alcohol
- Someone who genuinely enjoys starting conversations with strangers
- Reliable transportation, and the ability to lift cases of wine, tables, and a tent
- Weekend availability, especially spring and fall festival season
- Organized enough to handle cash, inventory, and a same-day report
Also included
- Paid every two weeks
- Commission on every wine club membership you sign up
- Mileage and tolls reimbursed when you transport our inventory
- Team wine, merch, and the best coworkers at any festival
Now Hiring
Social Media and Content Creator Intern
Your hourly is the floor, not the ceiling
Most internships pay you the same whether your work lands or not. This one does not. You get a set hourly rate, and you earn bonuses on top of it when your content actually performs.
We have a brand people genuinely love and more good material than we can keep up with: label art with a story, teachers we fund every month, and a booth full of happy customers every weekend. We need someone to capture it and turn it into content people want to watch.
This is a real portfolio-building role. You will own short-form video from idea to post, and you will see exactly how it performs.
What you will do
- Shoot and edit short-form video for TikTok, Instagram Reels, and YouTube Shorts
- Come to some weekend events to capture the booth, customers, and behind the scenes
- Turn our monthly featured teacher into content that makes people care
- Help plan and schedule a simple posting calendar
- Watch what performs and tell us what to make more of
How the bonuses work
- Performance bonus when a video you made takes off. If it goes big, you get paid for it going big.
- Commission on wine club signups that come through your content, tracked with your own link, the same deal our event captains get.
- Sales bonus tied to the orders your content drives.
- End of season bonus when we hit our growth goals together.
We will walk through the exact numbers on our first call, so you know what each one pays before you commit to anything.
What we are looking for
- 21 or older, since our content features alcohol
- You already make short-form video and can show us examples, even personal ones
- Comfortable on camera, or comfortable getting other people comfortable on camera
- Confident editing on your phone or in Capcut, Premiere, or similar
- Based in Maryland and able to get to occasional weekend events
- We care more about your feed than your major
Also included
- Flexible schedule that works around classes
- Real creative ownership and published work for your portfolio
- Wine and merch, plus event access
- Course credit if your school offers it, we are happy to work with your program
Why Tipsy Teacher
A small team doing something that matters
Teacher-founded
We fund a classroom every month
$1 from every bottle goes to a Maryland teacher until their goal is covered.
People actually like the product
4.9 stars from 107+ reviews and 50,000+ bottles sold.
Small team, real responsibility
No layers of approval. Your work goes out into the world quickly.
How to Apply
Send us a note
Email contact@tipsyteacher.com with the role in the subject line. Tell us a little about yourself and why this one caught your eye. A resume is welcome but not required.
1. You email us. For the internship, include links to content you have made. It does not need to be professional work.
2. We reply within about a week.
3. A short call to talk through the role, the pay, and your availability.
4. For captains, you shadow a real event before you run one on your own.
Both roles require you to be 21 or older because they involve serving, handling, or promoting alcohol. Tipsy Teacher Wines is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected characteristic.
