About the Role

We're seeking a scrappy, hands-on Sales Operations Specialist with a proactive, entrepreneurial spirit for our client in the hospitality industry. If you thrive in fast-paced startup environments, can wear multiple hats, and aren't afraid to do the groundwork, this role is perfect for you. As the frontline representative, you'll identify and connect with potential hosts, gather market insights, and drive new business by developing strategies and executing grassroots outreach.

Key Responsibilities

• Proactive Market Engagement
  • Conduct market visits and on-the-ground assessments
  • Evaluate listings and benchmark competitors/accommodations
  • Provide actionable insights for strategic planning
• Outbound Sales & Playbook Building * Execute cold outreach to prospective and churned hosts * Develop and iterate on sales strategies and pitches * Create scalable playbooks incorporating real-time feedback
• Digital & Community Operations * Actively participate in neighborhood-level social groups and digital forums * Engage with local communities to identify potential hosts and influencers * Foster relationships with industry professionals and local leaders
• Startup Mindset & Bias for Action * Display strong ownership and problem-solving abilities * Experiment with new strategies * Rapidly prototype tactics and operational processes
• Cross-functional Collaboration * Partner closely with Sales and Marketing teams * Test pitches and refine messaging based on real-time feedback

Qualifications

• 3-5 years of experience in a relevant field
• Proven background in outbound sales or grassroots operations
• Track record of successful cold outreach and business development
• Experience building or executing sales strategies for multi-sided marketplaces or direct-to-consumer businesses
• Previous startup experience in fast-paced, growth-focused environments
• Comfort operating with ambiguity and limited resources
• Strong organizational skills and ability to manage multiple priorities
• Clear communication skills with a positive, authentic tone
• Experience in customer success, community engagement, or field operations
• Empathy for small business owners and side hustlers
• Passion for hospitality and/or real estate (a plus)

Note : SaaS sales backgrounds are not a fit for this role.

Key Details

• Location : Must be located in NYC
• Duration : 9+ months (November 2025 - August 2026)
• Work Schedule : Full-time, 40 hours per week
• Pay Rate : Up to $60/hour
• Travel Requirements : Some local travel required
• Start Date : November 11, 2025