Sales Specialist

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This range is provided by Cypress HCM. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

$56.12/hr - $61.54/hr

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 MIAMI, FLORIDA
• Preference of being bilingual in Spanish
• 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‑side 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

Associate

Contract

Sales and Business Development

Internet Marketplace Platforms, Travel Arrangements, and Hospitality