Operations Management Jobs 2026 (Now Hiring) – Smart Auto Apply

About StaySouth:

StaySouth is a fast-growing, locally operated vacation rental management company based in Southeast Florida, managing properties across Miami, Miami Beach, Fort Lauderdale, and Palm Beach. Founded by Ricardo Remak, who spent more than 10 years in senior operations roles supporting reservations, guest communications, and client management across 20,000+ property bookings in the U.S. and U.K. That depth of operational experience, at scale, across markets, is the foundation StaySouth is built on.

We are part of the Casago franchise network, one of the largest vacation rental management platforms in North America, with 40,000+ homes. That means our owners and guests benefit from national-grade technology and distribution, while working directly with a local team that actually lives here and cares.

We are now building out our core team as we grow, and this role is a key part of that infrastructure.

About the Role:

This is not an admin position. The Business Development Representative- Property Management is a high-activity, relationship-driven role focused entirely on growing StaySouth's property portfolio. You will prospect, qualify, and convert property owners into long-term management clients - building a pipeline through outbound calls, texts, email, and social outreach.

The right person is confident on the phone, relentless with follow-up, motivated by performance income, and genuinely excited about helping property owners solve a real problem.Compensation:

•  $50,000 - $55,000 / OTE: $90,000
• Base salary is guaranteed. Commission is uncapped - your output determines your income.

What You'll Do:

• Source and identify new property owner leads daily from Zillow, Facebook Marketplace, Airbnb, expired listings, and investor networks
• Execute 250-500 outbound contacts per week via phone, text, email, and social media
• Build relationships with property owners and investors; identify pain points and management needs
• Qualify leads and schedule appointments for Ricardo and the management team
• Maintain accurate CRM records with detailed notes and follow-up schedules
• Follow up consistently with warm leads through structured cadences
• Report weekly on pipeline activity, conversion rates, and appointment outcomes
• Contribute to portfolio growth target of 2-5 signed management agreements per month

Lead Sources You Will Work:

• Zillow and Facebook Marketplace rental listings
• Airbnb and short-term rental owners
• Absentee and out-of-state property owners
• Expired rental listings
• Investor groups and networking events
• Realtor and client referrals
• Owners struggling with self-management
• Multi-property investors

Requirements

• 1+ year of outbound sales, appointment setting, or BDR experience
• Confidence and composure on the phone - you enjoy calling, not avoiding it
• Disciplined follow-up habits and CRM hygiene
• High activity tolerance- 250-500 outbound touches per week is the expectation, not the ceiling
• Self-motivated with a goal-oriented mindset and thick skin
• Clear, professional written and verbal communication

Nice to Have:

• Real estate, property management, or vacation rental industry experience
• Experience with outbound dialers and sales sequencing tools
• Familiarity with Airbnb, Vrbo, or short-term rental platforms
• Background in investor relations or business development

Benefits

• Health, dental, and vision benefits
• Paid time off and paid holidays
• Performance-based bonus opportunities
• CRM system, dialer, lead lists, email/text templates, and marketing materials provided
• Ongoing training and coaching from an operator with 10+ years of industry experience
• Growth opportunity within a scaling company - early team members grow with the business