Account Executive (North America - Remote - Insurance Tech)
- Compensation
- $20 / hr
- Location
- United States
- Work setup
- Remote
- Seniority
- Not specified
- Employment
- Not specified
- Experience
- 1+ years
- Category
- Sales
- Posted
Skills
Must have
- 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
Nice to have
- 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
Full description
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