Supply Sales Operations Specialist

Chris Baily; New York (NY); On-site; USD 77,000 - 84,000; Full time

Job summary

Chris Baily is seeking a hands-on Sales Operations Specialist to drive grassroots outreach, identify hosts, and gather market insights in a fast-paced startup setting.

You will work with Sales and Marketing to test pitches, build scalable playbooks, and own practical ops. The role requires a proactive mindset, travel willingness, and a passion for hospitality/real estate.

Qualifications

• 3-5 years of experience in relevant field.
• Scrappy self-starter with a proactive, hands-on approach.
• Excellent verbal and written communication.
• Strong organizational skills and multitasking abilities.
• Willingness to travel and local presence in NYC, Boston, or Philly.
• Experience in outbound sales or grassroots operations.
• Passionate about hospitality or real estate.
• Startup environment experience with ambiguity and limited resources.

Responsibilities

• Proactive Market Engagement: conduct market visits and assessments to evaluate listings and benchmark competitors.
• Outbound Sales & Playbook Building: perform cold outreach and develop scalable sales strategies and pitches.
• Digital & Community Ops: engage with local communities and forums to identify hosts and influencers.
• Startup Mindset & Bias for Action: take ownership, experiment, and prototype tactics quickly.
• Cross-functional Collaboration & Leadership: work with Sales and Marketing to test pitches and refine messaging.

Skills

Outbound sales

Communication

Organizational skills

People skills

Startup mindset

Travel readiness

Job description

Description

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

Duties

• Proactive Market Engagement: Conduct market visits and on-the-ground assessments to evaluate listings, benchmark competitors / accommodations, and provide actionable insights for strategic planning.
• Outbound Sales & Playbook Building: Execute cold outreach to prospective and churned hosts. Develop and iterate on sales strategies, pitches, and scalable playbooks, incorporating real-time feedback to drive impact.
• Digital & Community Ops: Actively participate in neighborhood-level social groups, digital forums, and local communities to identify and engage potential hosts and influencers. Foster relationships with industry professionals, organizers, and local leaders to find high-leverage opportunities.
• Startup Mindset & Bias for Action: Display a strong sense of ownership and problem-solving ability. Experiment with new strategies and rapidly prototype tactics and operational processes.
• Cross-functional Collaboration & Leadership: Partner closely with Sales and Marketing teams to test pitches and refine messaging based on real-time feedback.

Requirements

• 3-5 years’ experience
• Scrappy self-starter with a proactive, hands-on approach
• Natural people person—comfortable cold calling, chatting in group threads, or texting someone new
• Curious and energized by learning what makes local communities tick
• Highly organized and able to manage multiple conversations and priorities
• A clear communicator with a positive, authentic tone (voice, written, and digital)
• Passionate about our mission to build belonging and economic opportunity
• Experience in customer success, outbound sales, community engagement, or grassroots field operations
• Empathy for small business owners, hosts, or side hustlers
• Passion for hospitality and/or real estate
• MUST BE LOCATED IN NYC, BOSTON, OR PHILLY. NYC IS PREFERRED.
• Willingness to Travel
• Ideal Experience Startup Experience: Prior roles in fast-paced, growth-focused environments; comfortable operating with ambiguity and limited resources.
• Sales Expertise: Proven background in outbound sales or grassroots operations, with a track record of successful cold outreach and business development. Experience building or executing sales strategies for multi-sided marketplaces or direct-to-consumer businesses. Note: SaaS sales backgrounds are not a fit for this role.
• Industry Experience (A Plus): Real estate, hospitality, or similar / adjacent industries.
• Compensation: $56.12 – 61.54/hr W—2