Account Executive (North America - Remote - Insurance Tech)

Hospitable

9d•Remote

About The Position

Align Insurance Services is Hospitable's sister company — a licensed P&C brokerage built specifically for short-term rental operators and real estate investors. 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. 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.

Requirements

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 Haves

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

Responsibilities

Run the full sales cycle with inbound STR operators — from first conversation to signed deal — across both the Hospitable platform and Align's insurance products
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 platform to close operational gaps that create risk — guest screening, damage protection, smart lock and noise monitoring, automated messaging — reducing the client's exposure to damage and liability claims before insurance is even the topic
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 as parallel toolkits, not separate jobs