Account Executive (North America - Remote - Insurance Tech)

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. The 2020 Companies affiliation is about employment structure, not who you work with or for. We're hiring an Account Executive to run a full desk selling both Hospitable 's STR management platform and Align's insurance products to real estate investors. This isn't a pure insurance role and it isn't a pure SaaS role — it's both, sold together, to the same inbound client. You'll work warm, inbound leads from Hospitable 's real estate investor network. No cold prospecting. Your job is to diagnose how a host runs their STR business, sell them the Hospitable tools that fix operational gaps, and pair that with the right insurance coverage from Align to protect the investment. Same conversation, two products, one close. 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 requir