Account Executive (North America - Remote - Insurance Tech)

Hospitable.com; United States; On-site; USD 25,000 - 30,000; Full time

Benefits offered by this job

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 employee

Employee Assistance Program

Leadership Development Program

Established inbound client pipeline

Full-desk ownership — you run from to

Licensing support and paid study time

Carrier network access

Path to specialize in proptech and 보험

Job summary

Hospitable.com is hiring an Account Executive to run a full desk selling Align Insurance products to real estate investors within the Hospitable ecosystem. You’ll own discovery through close, leverage a warm inbound pipeline, and work remotely from the U.S.

with licensing support to obtain a P&C license within 30 days. You’ll earn $19.50/hour plus uncapped monthly bonuses, with weekly pay and a comprehensive benefits package.

Qualifications

• 1–2 years in SDR/BDR or closing sales in SaaS, proptech, or insurance.
• Experience running a full sales cycle.
• Able to learn Hospitable software and configure it live with a client.
• Excellent written and verbal communication.
• Able to manage a remote pipeline independently.
• US-based and available during US business hours.
• Willing to obtain a P&C license within 30 days of start.
• Pass background check.

Responsibilities

• Run the full sales cycle with STR operators—from first conversation to signed deal.
• Diagnose client STR operations: entity structure, property count, current tools, current coverage.
• Configure and sell Hospitable's property protection platform to close gaps.
• Quote and present Align's insurance coverage across carrier platforms post-licensing.
• Explain how ownership structure and portfolio strategy affect risk and sell accordingly.
• Support clients across short-, mid-, and long-term rental strategies and renovations.
• Build renewal pipeline by revisiting client accounts as portfolios grow and usage changes.
• Maintain clean, accurate CRM records and act as a system-of-record.

Skills

Full sales cycle

Remote work

SaaS/Proptech/Insurance knowledge

Strong communication

Tools

HubSpot

Applied Epic

HawkSoft

EZLynx

Job description

• Health/Dental/Vision benefits

Align Insurance Services is Hospitable's sister company — a licensed P&C brokerage built specifically for short-term rental operators and real estate investors. Same leadership, same customer base, different license. This role is hired and employed through our staffing partner, 2020 Companies, but you'll work directly alongside Hospitable and Align's leadership and sales teams day to day — same Slack, same pipeline, same standups.

We're hiring an Account Executive to run a full desk selling insurance products to real estate investors. Our insurance products are built into the core Hospitable product so you'll apply your insurance knowledge and use the product to assist automating insurance and protection programs.

You'll work warm, inbound leads from Hospitable's real estate investor network. Your job is to diagnose how a host runs their STR business and sell them the set of insurance tools that protect their business and their properties.

This role is built for SDRs and BDRs who are done qualifying leads for someone else to close. You'll own the full cycle — discovery, demo, quote, close, renewal.

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

Schedule: Monday-Friday, 40 hours per week

Work Location: Remote - U.S. Based

Licensing: No P&C license required to start. You must obtain an active P&C Insurance license within your first 30 days of employment as a condition of continued employment in this role.

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
• Full-desk ownership — you run discovery through close, not a slice of the funnel
• Licensing support and paid study time to get your P&C license in your first month
• Access to a carrier network and specialized insurance solutions
• Path to specialize in a high-growth niche at the intersection of proptech and insurance

Job Description

• Run the full sales cycle with STR operators — from first conversation to signed deal
• Diagnose how each client runs their STR business: entity structure, property count, current tools, current coverage, and where risk is being carried unnecessarily
• Configure and sell Hospitable's property protection platform to close operational gaps that create risk
• Once licensed, quote and present Align's insurance coverage across carrier platforms, identifying gaps in existing policies and recommending the right layered protection
• Explain how ownership structure, portfolio strategy, and platform configuration all feed into the client's real risk profile — and sell against that, not a script
• Support clients across short-term, mid-term, and long-term rental strategies, plus renovation projects
• Build renewal pipeline by revisiting client accounts as their portfolios grow and their Hospitable usage and coverage needs change
• Keep clean, accurate records in the CRM and agency management system — this is a system-of-record job, not a memory job
• Complete P&C licensing within 30 days, then complete Align's carrier and product training to run insurance conversations independently
• Work daily with the Hospitable product and Align's carrier network

Qualifications

• 1-2 years in an SDR, BDR, or closing sales role — SaaS, proptech, or insurance background all considered
• Demonstrated ability to run a full sales cycle, not just generate or qualify leads
• Comfortable learning a technical software product (Hospitable) well enough to configure it live with a client, not just describe it
• Strong verbal and written communication — you can explain a product feature and an insurance exclusion in the same call without losing the client
• Able to work independently and manage a full pipeline in a remote environment
• Must be U.S.-based and available during standard U.S. business hours across multiple time zones
• Willing and able to obtain a P&C insurance license within 30 days of start (Align covers study materials and exam costs)
• Able to pass required background check

Preferred Skills & Experience

• Prior experience selling to real estate investors, property owners, or STR operators
• Familiarity with short-term rental operations — guest management, damage protection, smart home devices
• Understanding of how LLCs and other entity structures affect liability
• Experience with CRM or agency management platforms (HubSpot, Applied Epic, HawkSoft, EZLynx, or similar)
• Comfortable in AI-enabled workflows and fast-moving tool stacks

Benefits

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.