Careers at Paint and Sip Portland

At Paint & Sip Portland, we believe art should be accessible, joyful, and shared. Our events bring people together in restaurants, wineries, breweries, community spaces, and private venues throughout the Portland area to create something beautiful - no experience required.

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Our instructors play a big role in making these events special. They guide guests step-by-step through a painting while creating a welcoming, fun atmosphere where everyone feels comfortable exploring their creativity.

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Working with Paint & Sip Portland is a great fit for artists who enjoy teaching, connecting with people, and bringing positive energy to a room.

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Our events take place across the Portland metro area and offer a flexible way to share your artistic skills while meeting new people and exploring different venues around the city.

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Current Opportunities

Contract Artist Instructor –

East Portland / East Metro Area

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We are currently hiring a contract artist instructor to support paint and sip events on Portland’s east side, including areas such as Happy Valley, Troutdale, and surrounding communities.

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This role is ideal for an artist who enjoys teaching, engaging with groups, and creating a fun and welcoming environment for participants of all skill levels.

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Responsibilities

• Lead paint and sip events by guiding guests step-by-step through a painting
• Create a welcoming and encouraging environment for participants of all skill levels
• Set up and break down painting materials and supplies
• Communicate clearly and confidently with groups
• Maintain a fun and engaging atmosphere during events
• Travel to event locations on Portland’s east side and surrounding areas
• Represent Paint & Sip Portland professionally at venues and events

Qualifications

• Minimum 3 years of painting experience (acrylic preferred)
• Previous teaching experience (art classes, workshops, camps, etc.)
• Comfortable speaking in front of groups
• Friendly, personable, and charismatic personality
• Strong verbal communication skills related to art instruction
• Comfortable working with people of all ages and abilities, including children, seniors, and individuals with disabilities
• Open and accepting of people from all backgrounds
• Reliable vehicle and ability to travel to locations such as Troutdale, Happy Valley, and other east Portland areas
• Flexible schedule with evening and weekend availability

Compensation & Perks

• $100 per event (starting pay)
• Tips are allowed and can be collected by the instructor
• Mileage reimbursement for travel to event locations
• All paint, supplies, and equipment provided
• Paint & Sip Portland t-shirt or hoodie in the color of your choice
• Fun and creative work environment
• Opportunity to explore new venues and areas around Portland

Requirements

• Must provide 1 personal reference and 2 professional/work references

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👉 Apply here