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Freelance Wingman Jobs (NOW HIRING)

The Tie Bar

Associate Creative Director

Chicago, IL · On-site +1

... wingman for showing up sharp, stylish, and ready for any moment. We're looking for an Associate ... Manage relationships with external freelancers, photographers, stylists, and production partners as ...

The Tie Bar

Associate Creative Director

Chicago, IL · On-site

... wingman for showing up sharp, stylish, and ready for any moment. We're looking for an Associate ... Manage relationships with external freelancers, photographers, stylists, and production partners as ...

Tie Bar

Associate Creative Director

Chicago, IL · On-site

... wingman for showing up sharp, stylish, and ready for any moment. We're looking for an Associate ... Manage relationships with external freelancers, photographers, stylists, and production partners as ...

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Freelance Wingman information

See salary details

$14

$47

$132

How much do freelance wingman jobs pay per hour?

As of Aug 3, 2026, the average hourly pay for freelance wingman in the United States is $47.71, according to ZipRecruiter salary data. Most workers in this role earn between $24.28 and $61.78 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Freelance Wingman, and why are they important?

To thrive as a Freelance Wingman, you need strong interpersonal skills, situational awareness, and experience in social settings, often with a background in hospitality or event environments. Familiarity with social media, messaging apps, and basic client management tools is useful for communication and scheduling. Exceptional listening skills, discretion, and the ability to quickly build rapport help you stand out in this role. These skills are crucial for ensuring client comfort, effective social support, and positive, safe experiences in various social contexts.

How does a Freelance Wingman typically collaborate with clients to ensure a comfortable and successful social experience?

As a Freelance Wingman, you work closely with clients to understand their social goals, preferences, and boundaries before attending events together. You'll often spend time discussing strategies, offering real-time feedback, and providing encouragement to help clients build confidence in social settings. The role involves adapting to different personalities and situations, ensuring the client feels supported and respected throughout the experience. Open communication and professionalism are key, as each client's needs and comfort levels can vary widely.

What are freelance wingmen?

Freelance wingmen are professionals who assist clients in social situations, often to help them meet new people, build confidence, or improve their dating experiences. Unlike traditional friends or acquaintances, these individuals are hired specifically for their social skills and ability to provide support in public settings such as bars, parties, or networking events. Their services can include giving feedback on social interactions, offering conversation starters, and helping to ease social anxiety. Freelance wingmen work independently or through agencies and are typically paid by the hour or by the event.

What is the difference between Freelance Wingman vs Sales Assistant?

AspectFreelance WingmanSales Assistant
CredentialsVaries; often self-taught or industry-specific experienceTypically high school diploma or equivalent
Work EnvironmentRemote or on-site, flexible hours, project-basedRetail or office settings, fixed hours
Employer & Industry UsageFreelance clients, startups, sales teamsRetail stores, corporate sales departments

Freelance Wingmen often work independently, providing sales or support services on a flexible basis, while Sales Assistants typically work in retail environments with structured hours. Both roles involve customer interaction but differ in work setting and credentials required.

What cities are hiring for Freelance Wingman jobs? Cities with the most Freelance Wingman job openings:
What are the most commonly searched types of Wingman jobs? The most popular types of Wingman jobs are:
Freelance Wingman jobs near you
Infographic showing various Freelance Wingman job openings in the United States as of July 2026, with employment types broken down into 61% Full Time, 13% Part Time, 2% Temporary, and 24% Contract. Highlights an 60% Physical, 2% Hybrid, and 38% Remote job distribution, with an average salary of $99,230 per year, or $47.7 per hour.

Associate Creative Director

The Tie Bar

Chicago, IL • On-site, Remote

Full-time

Posted 25 days ago

Job description

Associate Creative Director

Chicago, IL (Hybrid) | Full-Time

The Tie Bar is known for premium menswear, offering an extensive assortment of ties, accessories, and tailored essentials. Through thoughtful design and quality craftsmanship, we help customers build a polished wardrobe with confidence-your ultimate wingman for showing up sharp, stylish, and ready for any moment.

We're looking for an Associate Creative Director to lead the concepting, direction, and execution of brand and product storytelling across all consumer touchpoints, with a primary focus on direct-to-consumer channels. You'll lead a nimble creative team spanning design, copy, and visual merchandising/styling, ensuring The Tie Bar's brand is expressed consistently and compellingly across digital, retail, and physical experiences.

If you're equally comfortable art directing a photoshoot, mentoring a creative team, developing seasonal campaigns, and optimizing creative for performance, we'd love to meet you.

You'll:
  • Lead the development of seasonal campaigns, including concepting, moodboards, and art direction aligned with brand and customer positioning
  • Direct photo and video shoots, overseeing concept development, casting, styling, and on-set creative direction
  • Manage and mentor a small creative team, providing clear direction, feedback, and professional development
  • Collaborate with merchandising and product teams to identify storytelling opportunities that highlight key categories and occasions
  • Partner with e-commerce and marketing teams to create high-performing digital assets across email, website, paid media, and social
  • Concept and oversee paid social campaigns; analyze performance and iterate creative in partnership with performance marketing
  • Guide retail creative and visual merchandising direction to ensure consistency with broader brand campaigns
  • Design and oversee brand assets including packaging, lookbooks, presentations, and in-store materials
  • Manage relationships with external freelancers, photographers, stylists, and production partners as needed
What We're Looking For

You're a versatile creative leader who understands that great brand storytelling is both beautiful and conversion-minded.

You bring:

  • 5-7 years of experience in a creative, art direction, or design role, preferably within men's fashion, accessories, or DTC lifestyle brands
  • Excitement to be part of our Chicago-based team, with an appreciation for the city's creative and retail community
  • Prior experience managing or mentoring creative team members
  • A strong portfolio demonstrating campaign development, brand storytelling, and multi-channel execution with a focus on digital performance
  • Experience leading photoshoots and content production with a refined eye for men's styling, composition, and detail
  • Proficiency in Adobe Creative Suite (Photoshop, InDesign, Illustrator) and presentation/design tools (Figma, Keynote, etc.)
  • Strong understanding of ecommerce best practices and performance-driven creative
  • Excellent communication, organizational, and project management skills
Bonus Points If You...
  • Have a passion for men's style, tailoring, and occasion-based dressing
  • Appreciate classic design with a modern sensibility
  • Thrive in a fast-paced, entrepreneurial environment where resourcefulness and agility are essential
Why You'll Love This Role

This isn't a production-only creative position.

You'll be a key steward of the brand-shaping how The Tie Bar shows up across ecommerce, retail, and marketing while leading and developing a small, high-performing creative team. You'll own projects from concept through production, bridging digital and physical brand experiences to create a seamless, omnichannel story.

If you're energized by building brands through elevated, conversion-minded creativity, we'd love to meet you.

Who We Are

The Digital Stronghold is a portfolio of five brands spanning performance athletics and everyday style, including Taylor Stitch, The Tie Bar, Boston Scally, Pedal Mafia, and Glade Optics. Each brand has its own loyal community and distinct point of view, and together they cover a broad range of how men live, perform, and dress.

We are creators, builders, and collaborators. We believe in design-led thinking, thoughtful storytelling, and delivering products and experiences that our consumers truly love.

Our Values
  • Own the Outcome
  • Move with Purpose
  • Speak Truth, Listen Fully
  • Learn and Share
  • Drop the Ego
  • Build for the Long Haul

Location: Chicago, IL (Hybrid) - on-site as needed,, with flexibility for remote work based on business needs

Travel: 10-20% (photoshoots, production, and store visits)

Ready to lead creative that moves a brand forward? Apply today and share your portfolio-we can't wait to see what you'll build.

Employment Type: FULL_TIME

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