Head Concierge

Outfit is a venture-backed startup in Chicago, exploring how AI can transform where people go and why.

Although we're pre-market, we’re building products with the belief that:

• People are unique and deserve to be listened to.
• Wherever someone chooses to go, stay, eat, work, or play should reflect who they are, not the average of everyone else.
• Technology should make our collective experiences more human and personal, never less.

If you share our beliefs—and our love for people, maps, recommendations, and listening—then we’d love to talk to you.

The Role

We're looking for a Head Concierge to pioneer our premium travel advisory service and shape the future of personalized travel experiences. This role combines the art of hospitality with the science of AI-powered technology, offering an opportunity to transform how people discover and experience places that truly resonate with them.

This role will be the primary candidate to lead operations and service for us in the future.

What You'll Do

• Lead the development and growth of our travel advisory business from the ground up
• Evaluate and implement travel technology platforms and tools to enhance our service delivery
• Provide hands-on concierge service to our initial customers, setting the standard for exceptional service
• Develop standard operating procedures and best practices for future concierge team members
• Collaborate with our engineering team to improve our AI-powered recommendation systems
• Become an expert at the intersection of AI and travel
• Take what you've learned and impact product development

Requirements

About You

• Self-starter mentality: You take initiative and create structure in ambiguous situations
• Natural relationship builder: You forge meaningful connections with both clients and partners
• Service-oriented mindset: You anticipate needs and delight in exceeding expectations
• Strategic thinker: You can balance immediate customer needs with long-term business goals
• Adaptability: You thrive in a fluid, fast-paced environment where requirements may change rapidly
• Ownership mindset: You treat the company's success as your personal mission
• Technology enthusiast: You're excited about how AI can enhance rather than replace human service

Your Experience & Skills

• 5+ years of experience in hospitality, travel advisory, or related customer service roles
• Proven track record of building and maintaining high-touch client relationships
• Experience with travel booking systems and GDS platforms
• Strong project management skills and ability to create processes from scratch
• Excellence in written and verbal communication
• Demonstrated ability to work with technical teams
• Knowledge of luxury travel market trends and destinations
• Experience managing vendor relationships and partnerships

Nice to Have

• Experience at a brand or high-end travel agency
• Startup experience or experience building functions from scratch
• Familiarity with AI/ML concepts and applications
• Background in operations management
• Experience with CRM systems and customer service tools

Benefits

Our Values

• Listen First: We are curious, empathetic, and authentic. We listen to our teammates and show up prepared to be listened to. We talk to our customers and prove hypotheses using data. We are inclusive and open-minded. We leave our egos at the door and win as a team
• Build with Optimism: We take big swings and bias toward action. We prioritize the hardest puzzles knowing great things require persistence. We invent products, concepts, and ways of working, celebrating both the successes and the learnings.
• Leave it Better: We want a better world for our kids. We don't stay in our lanes - we take out our trash, comment on each other's code, engage in healthy debate, and build things we can be proud of. We use AI responsibly.
  

Benefits & Why Join Outfit Labs?

• Be part of a small team changing how people experience the world
• Work on challenging problems at the intersection of AI and human experience
• Flexible work environment with a focus on work-life balance
• Access to cutting-edge AI tools to boost your productivity
• Medical, Vision, and Dental benefits

We're looking for people ready to roll up their sleeves and build something extraordinary. If you're excited about turning a vision into reality and willing to put in the work, we'd love to hear from you.

Even if you don't meet every requirement, we'd still like to hear from you. We're seeking individuals eager to learn and grow with us.

Important Notes

• This position requires working on-site at our West Loop, Chicago office at least 3 days per week
• Relocation assistance is not provided
• Remote work is not available for this role
• Candidates must be legally authorized to work in the United States
• We are unable to provide visa sponsorship or support visa transfers for this position

Outfit Labs is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.