Trainee Short Term Rentals Jobs (NOW HIRING)

Job Type:

Work Location:

Overview:

We are seeking a licensed Property & Casualty Insurance Producer to partner with Align Insurance Services, a specialized brokerage serving real estate investors nationwide. This remote role focuses on providing consultative insurance solutions by helping clients assess their coverage needs, identify potential gaps, and select policies that best protect their investments.

Through our partnership with Hospitable, a leading platform for short-term rental operators, this position works with an established inbound client base rather than traditional cold prospecting. The ideal candidate has property-focused P&C insurance experience, strong communication skills, the ability to explain coverage options clearly, and a passion for building trusted client relationships.

Pay: $19.50/hour + uncapped performance-based monthly bonuses

Schedule: Monday-Friday, 40 hours per week

Work Location: Remote - U.S. Based

Required: Active P&C Insurance license

What We Offer

• Weekly pay
• Monthly sales bonus opportunities
• Next day pay with DailyPay
• Health/Dental/Vision benefits
• 401K Program with matching
• Paid Time Off
• Paid Holidays
• Mobile Reimbursement
• Scholarship opportunities for employees and direct family members
• Employee Assistance Program
• Leadership Development Program
• Established inbound client pipeline through Hospitable's real estate investor network
• Opportunity to specialize in a growing niche within real estate investor insurance
• Access to a carrier network and specialized insurance solutions
• Opportunity to build long-term client relationships through consultative advising

Job Description:

• Manage the full insurance sales process from initial client engagement through policy binding and ongoing account support
• Conduct consultative conversations with real estate investors to understand their portfolio, investment strategy, entity structure, risk exposure, and coverage needs
• Review existing policies to identify coverage gaps and provide clear, well-informed recommendations
• Quote, analyze, and present insurance options across multiple carrier platforms to identify the best solutions for each client
• Advise clients on layered protection strategies, including traditional Property & Casualty coverage and additional protection solutions available through Align's preferred partnerships
• Educate clients on how property ownership structures, liability exposure, and investment strategies impact their insurance needs
• Support clients with coverage for various real estate investment strategies, including:
  • Short-term rentals
  • Mid-term rentals
  • Long-term rentals
  • Property renovations
• Build and maintain strong client relationships through timely communication, knowledgeable guidance, and proactive service
• Drive renewal opportunities by reviewing client needs as portfolios expand and coverage requirements evolve
• Maintain accurate client records and documentation within agency management systems
• Collaborate with internal teams and preferred partners to deliver a comprehensive client experience
• Complete onboarding and training to learn Align's carrier relationships, workflows, systems, and specialized real estate investor insurance approach

Qualifications

• Must have an active Property & Casualty insurance license in good standing
• 1-2 years of experience selling Property & Casualty insurance, with a focus on property-related coverage preferred
• Strong understanding of insurance policies, coverage terms, exclusions, and risk assessment
• Ability to clearly explain complex insurance concepts to clients in a simple, professional manner
• Excellent verbal and written communication skills with strong relationship-building abilities
• Ability to work independently, manage priorities, and maintain consistent productivity in a remote environment
• Must be U.S.-based and available during standard U.S. business hours across multiple time zones
• Ability to successfully complete required background check

Preferred Skills & Experience

• Experience with dwelling fire, landlord, vacation rental, or short-term rental insurance coverage
• Experience working with real estate investors, property owners, or investment-focused clients
• Understanding of how business entities (LLCs, S-Corps, etc.) impact liability and insurance needs
• Experience using agency management systems such as Applied Epic, HawkSoft, EZLynx, or similar platforms
• Comfort working with technology-driven workflows and AI-enabled tools

What You Can Expect From 2020 Companies
We welcome every voice, and we are committed to building a truly inclusive environment where your differences are not just welcomed, they are celebrated. We are always identifying opportunities to encourage our team to be their authentic selves, while working to provide a best-in-class experience for our employees. Whether that's paid holidays, long-term career pathing options, personal development opportunities or professional stretch assignments, you can expect 2020 Companies to support you.
2020's Commitment
We are committed to creating a diverse and inclusive organization and are proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, pregnancy, disability, age, veteran status, or other dimensions of identity.