Cypress HCM · 4 months ago
Supply Sales Operations Specialist
Cypress HCM is looking for a proactive and entrepreneurial Sales Operations Specialist who thrives in fast-paced startup environments. The role involves engaging with potential hosts, conducting market assessments, and collaborating with Sales and Marketing teams to drive new business and refine strategies.
Human ResourcesInformation TechnologyStaffing Agency
Responsibilities
Conduct market visits and on-the-ground assessments to evaluate listings, benchmark competitors / accommodations, and provide actionable insights for strategic planning
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
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
Display a strong sense of ownership and problem-solving ability. Experiment with new strategies and rapidly prototype tactics and operational processes
Partner closely with Sales and Marketing teams to test pitches and refine messaging based on real-time feedback
Qualification
Required
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
Preferred
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