H

Hospitable

SaaS platform automating short-term rental operations

Account Executive - Insurance Tech

Full-Time
$19.50/hr+ Uncapped performance-based monthly bonuses
Junior
Remote in USA
RemoteMust work during standard U.S. business hours across multiple time zones.
InsuranceInsurance Sales & Agency

About the job

Requirements
  • One to two years of experience in an sales development representative, business development representative, or closing sales role; SaaS, proptech, or insurance backgrounds are considered.
  • Demonstrated ability to run a full sales cycle rather than only generate or qualify leads.
  • Ability to learn and configure a technical software product live with a client.
  • Ability to explain product features and insurance exclusions clearly in the same client conversation.
  • Ability to work independently and manage a full pipeline in a remote environment.
  • Must be based in the United States and available during standard U.S. business hours across multiple time zones.
  • Willingness and ability to obtain a property and casualty insurance license within 30 days of starting employment.
  • Ability to pass the required background check.
Responsibilities
  • Run the full sales cycle with short-term rental operators from the first conversation through signed deal.
  • Diagnose each client's short-term rental business, including entity structure, property count, current tools, current coverage, and unnecessarily carried risk.
  • Configure and sell the property protection platform to close operational gaps that create risk.
  • After licensing, quote and present insurance coverage across carrier platforms, identify gaps in existing policies, and recommend layered protection.
  • Explain how ownership structure, portfolio strategy, and platform configuration affect the client's risk profile, and sell against that profile rather than a script.
  • Support clients across short-term, mid-term, and long-term rental strategies, as well as renovation projects.
  • Build a renewal pipeline by revisiting client accounts as portfolios, platform usage, and coverage needs change.
  • Maintain clean and accurate records in the customer relationship management system and agency management system.
  • Complete property and casualty licensing within 30 days, then complete carrier and product training to conduct insurance conversations independently.
  • Work daily with the product and carrier network.
Desired Qualifications
  • Prior experience selling to real estate investors, property owners, or short-term rental operators.
  • Familiarity with short-term rental operations, including guest management, damage protection, and smart home devices.
  • Understanding of how limited liability companies and other entity structures affect liability.
  • Experience with customer relationship management or agency management platforms such as HubSpot, Applied Epic, HawkSoft, EZLynx, or similar.
  • Comfort working in artificial-intelligence-enabled workflows and fast-moving tool stacks.

About the company

Hospitable provides SaaS tools that help short-term and vacation rental hosts automate operations. It automates guest messaging with a unified inbox and AI responses, and syncs calendars with Airbnb, Vrbo, and Booking.com to avoid double bookings; hosts can also build direct booking websites with payments, guest screening, and damage protection. The platform supports team collaboration, smart-home integrations for check-ins and energy management, and a pricing tool that uses market data to suggest nightly rates. Its goal is to reduce hosts’ administrative workload while helping them grow revenue through automation and direct bookings, serving both individuals and property managers with scalable plans.

Company Size

51-200

Company Stage

Early VC

Total Funding

$2.7M

Headquarters

New York City, New York

Founded

2016

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Simplify's Take

What believers are saying

  • Hospitable raised $1.5 million from users and employees on September 18, 2026.
  • Hospitable says 25,000+ hosts and property managers use the platform daily in 2026.
  • Cleaner Marketplace, trip insurance, and direct-booking integrations create new revenue beyond subscriptions.

What critics are saying

  • September 2026 status logs showed login, messaging, and website incidents after deploys.
  • Airbnb, Vrbo, and Agoda API dependence gives rivals and platforms leverage over Hospitable revenue.
  • Freemium pricing invites low-margin hosts, while enterprise PMS rivals attack with deeper integrations.

What makes Hospitable unique

  • April 2026 Essentials made core channel management free across Airbnb, Vrbo, Booking.com.
  • Hospitable’s Apps Marketplace now connects STR Desk, OpenRoom, GuestArrive, and ECBYO workflows.
  • Direct bookings, cleaner sourcing, taxes, insurance, and messaging live inside one STR operating system.

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Benefits

Health Insurance

Remote Work Options

Paid Vacation

Parental Leave

Mental Health Support

Company Equity

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

2%

2 year growth

9%
EIN Presswire
Sep 28th, 2026
Emerald Coast By Owner and Hospitable launch new integration to make Gulf Coast direct bookings easier.

Emerald Coast By Owner and Hospitable launch new integration to make Gulf Coast direct bookings easier. September 28, 2026, 18:00 GMT Vacation rental hosts can now seamlessly connect their Hospitable properties to ECBYO, reach more Gulf Coast travelers and offer guests direct bookings DESTIN, FL, UNITED STATES, September 28, 2026 /EINPresswire.com/ - DESTIN, Fla. - September 28, 2026 - Emerald Coast By Owner (ECBYO), a Gulf Coast-focused vacation rental marketplace, has announced a new integration with Hospitable, a leading vacation rental management platform. The integration allows Hospitable users to connect eligible properties to ECBYO and streamline the process of reaching travelers who prefer to book directly with vacation rental hosts. The integration brings together two companies that support the Book Direct movement and its goal of creating a more transparent relationship between vacation rental hosts and guests. Instead of relying exclusively on large online travel agencies that may add service fees to the advertised rental rate, ECBYO connects travelers directly with property owners and professional managers. Depending on the property, travel dates and booking platform being compared, booking directly may help guests save up to 20% on their vacation rental. "Travelers should be able to understand what they are paying for, communicate directly with the people responsible for their rental and avoid unnecessary platform fees whenever possible," said Joe Godar of Emerald Coast By Owner. "Our new Hospitable integration makes it easier for hosts to reach direct-booking guests without adding another complicated system to manage." A Simpler Way to List on ECBYO Hospitable users can connect their account to their ECBYO owner account and select the properties they want displayed on the ECBYO network. Once authorized, ECBYO can synchronize important property information from Hospitable, including: Property descriptions Photographs Rates and pricing Calendar availability Blocked dates This process reduces the repetitive work associated with joining another vacation rental marketplace. Hosts do not have to manually rebuild every listing, upload the same photographs again or maintain a separate availability calendar. Travelers can view current property information, check availability, receive a quote and complete their booking through ECBYO. Reservations generated through ECBYO are then managed within the host's Hospitable account. Depending on the host's Hospitable plan and account configuration, hosts can review booking requests, communicate with guests, make reservation changes, manage cancellations and request or send payments through their existing Hospitable workflow. Gulf Coast Marketing Meets Vacation Rental Automation ECBYO is designed specifically for travelers searching for Gulf Coast Vacation Rentals. Its inventory includes beachfront condominiums, beach houses, pet-friendly properties, private-pool homes and other professionally managed vacation accommodations. ECBYO promotes properties across Florida, Alabama, Mississippi, Louisiana and Texas, including the Florida Panhandle, Southwest Florida, Florida's west coast and the Florida Keys. Hospitable provides hosts and property managers with tools that help simplify the daily operation of short-term rentals. Its platform supports synchronized calendars, centralized guest communication, automated messaging, direct-booking management, team access, task coordination, payment processing, reporting and channel management. Together, the two platforms offer a practical combination. Hospitable helps hosts manage their rental operations, while ECBYO places Gulf Coast properties in front of travelers actively searching for direct-booking opportunities. Hosts can maintain property information and manage reservations through Hospitable while using ECBYO as an additional source of bookings. This can reduce administrative work, lower the risk of outdated availability and help hosts diversify beyond the largest online travel agencies. Direct Booking Benefits Hosts and Guests Direct booking gives hosts greater control over the guest relationship. Owners and managers can answer property-specific questions, explain rental policies and provide local recommendations before the reservation is completed. This direct communication is particularly valuable along the Gulf Coast, where travelers may need detailed information about beach access, parking, boats, pets, pools, accessibility, resort amenities and local rules. Hosts can also build stronger guest relationships, generate repeat business and establish a recognizable rental brand. Returning guests can contact the host directly for future vacations rather than starting over on an unrelated travel platform. For travelers, one of the most significant advantages is the potential savings. Major vacation rental platforms may add guest service fees that increase the final price beyond the nightly rate initially displayed. These charges can become substantial for longer stays, larger homes and peak-season reservations. ECBYO does not charge travelers a traditional guest service fee. Because guests can book directly with the host or property manager, the final cost may be up to 20% lower than a comparable reservation that includes a large platform service fee. Actual savings will vary based on rental rates, taxes, host charges, travel dates and the platform being compared. Helping Hosts Diversify Their Marketing The ECBYO and Hospitable integration does not require hosts to leave their other booking channels. Instead, it provides another way to diversify their marketing and reduce dependence on any single marketplace. A balanced distribution strategy can help vacation rental businesses reach more travelers while gradually increasing their share of direct reservations. The integration can be especially valuable for professional property managers with multiple Gulf Coast rentals. Synchronizing property information can save significant time compared with manually creating and maintaining individual listings. Managers can select which properties to publish and manage resulting reservations through the Hospitable system they already use. How to Get Started Hospitable users can begin by creating an ECBYO owner account and selecting the number of properties they want to list. From the ECBYO owner dashboard, users can open the Integrations section, select "Connect with Hospitable" and securely authorize the connection through Hospitable. After authorization, the host selects the appropriate properties, and the ECBYO team reviews the imported listings before publishing them on the relevant Gulf Coast destination pages. The new integration is available now. About Emerald Coast By Owner Emerald Coast By Owner, also known as ECBYO, is a direct-booking vacation rental marketplace connecting Gulf Coast travelers with verified property owners and professional managers. ECBYO promotes vacation rentals across Florida, Alabama, Mississippi, Louisiana and Texas while supporting transparent pricing, direct communication and bookings without an ECBYO guest service fee. Visit EmeraldCoastByOwner.com to search Gulf Coast vacation rentals or learn more about listing a property. About Hospitable Hospitable provides vacation rental software that helps hosts and property managers automate guest communication, synchronize calendars, coordinate operations, manage reservations and grow direct bookings. Visit Hospitable.com for more information. Legal Disclaimer: EIN Presswire provides this news content "as is" without warranty of any kind. We do not accept any responsibility or liability for the accuracy, content, images, videos, licenses, completeness, legality, or reliability of the information contained in this article. If you have any complaints or copyright issues related to this article, kindly contact the author above. You just read: September 28, 2026, 18:00 GMT EIN Presswire's priority is author transparency. We do our best to weed out false and misleading content. The content above is the sole responsibility of the author who makes it available. If you have any complaints, kindly contact the author above. +1 513-708-3071

OpenRoom Travel
Sep 10th, 2026
OpenRoom is officially integrated with Hospitable.

OpenRoom is officially integrated with Hospitable. September 10, 2026 OpenRoom is thrilled to announce that its integration with Hospitable is now live. If you use Hospitable to manage your vacation rentals, you can now connect your account directly to OpenRoom and unlock the full potential of its platform. This partnership allows you to sync your properties instantly, automate your operations, and access all of OpenRoom's features to maximize your bookings and streamline your guest management. Ready to scale your business? Log into your OpenRoom dashboard today, connect your Hospitable account, and start managing your properties effortlessly. Click on the resources link to learn step by step how to connect Hospitable to OpenRoom. Resources: Guide prepared by Hospitable to help you integrate your account Help article prepared by OpenRoom to help you integrate your account 0 comments Join the conversation and share your perspective. No comments yet Be the first to start this conversation. Top comments. No top comments yet. Be the first to leave a liked comment!

Alertify
Jul 29th, 2026
Inside Alertify AQI+: how real-time air quality monitoring works.

Inside Alertify AQI+: how real-time air quality monitoring works. Every air quality problem a vacation rental host deals with, mold, poor ventilation, lingering vape aerosol, traces back to the same root cause: nobody was watching until it was too late. Alertify's indoor air quality monitoring device, known as AQI+, was built to close that gap by tracking everything that matters inside a unit, continuously, from one piece of hardware, rather than asking hosts to piece together several separate tools or rely on memory and guesswork. What the device actually tracks. AQI+ monitors humidity, temperature, CO2, and smoke or vapor particles in real time, covering the full range of conditions that quietly shape both guest comfort and property damage risk. It plugs directly into any standard outlet, connects to WiFi, and links to a unit through the Alertify dashboard in a setup process that takes about 15 minutes on-site. There are no cameras and no microphones involved, which means guest privacy stays fully intact while property conditions stay fully visible to the host, a distinction that matters both for guest trust and for compliance with platform policies that prohibit recording devices inside private living spaces. This combination of sensors matters because these conditions rarely occur in isolation. A unit with poor ventilation often also runs a higher humidity risk, since stale air circulates moisture less effectively than a well-ventilated space. Tracking all of these conditions together, rather than picking just one, gives hosts a genuinely complete picture rather than a partial one that might miss a related but distinct problem developing in the same unit. From sensor to alert to action. The moment a threshold gets crossed, whether that is rising humidity in a bathroom, elevated CO2 in a bedroom, or the first signs of indoor smoking, humidity and CO2 can be viewed on the dashboard on live graphs. Units with high humidity are flagged on the dashboard. Every event also gets logged and stored for more than 180 days, giving hosts a searchable history they can reference for maintenance planning, review disputes, or compliance documentation well after the fact. This is the same real-time detection and logging covered throughout its guide to indoor air quality monitoring for vacation rentals, just packaged into a single device that handles the full range of conditions discussed there. Built for hosts managing more than one property. For hosts running a single seasonal rental, AQI+ means one less thing to check manually between guests. For hosts managing a larger portfolio, the value scales directly: the dashboard consolidates readings across every unit into one view, which is exactly what a property monitoring system needs to do to be useful at any size. Rather than logging into separate systems or physically visiting each property to get a sense of overall portfolio health, a host can scan a single dashboard and immediately see which units, if any, need attention. Alertify also integrates directly with the platforms hosts already use daily, including Airbnb, Guesty, Hospitable, and Hostex, so air quality alerts show up alongside booking and guest communication tools rather than living in a separate app nobody checks. That integration is a deliberate design choice, since even the best monitoring system provides little value if hosts do not actually see and act on its alerts in the flow of their normal daily workflow. Alertify built AQI+ specifically for the realities of short-term rental management, where hosts cannot be on-site to catch a problem the moment it starts. See what AQI+ can tell you about your own properties. Book a demo and get a real look at what's happening inside your units right now.

HostReply
Jul 26th, 2026
Who should choose StayReply.

Who should choose StayReply. * You run a PMS HostReply doesn't support yet. StayReply's broader integration list covers more ground today if you're not on Hospitable or OwnerRez. * You manage a large, PMS-diverse portfolio. A multi-brand operator connecting several different PMSs across properties may find StayReply's one-tool-many-systems approach simpler than mixing tools per PMS. * You'd rather curate a knowledge base than rely on live lookups. If your property details rarely change and you're comfortable keeping a knowledge base updated, that model works fine. Who should choose HostReply. * You already use Hospitable or OwnerRez. Deep integration means live calendar and property lookups instead of a separately maintained knowledge base. * You want simple, flat, size-independent pricing. $19/property/month whether you run one property or fifty, with no tier table to check. * You want escalations to reliably reach you. HostReply's SMS escalation needs no app install and works on any phone. * You want FAQs that build themselves. HostReply detects repeated guest questions automatically and proposes new FAQ entries for approval, instead of relying only on what you feed a knowledge base up front. For the wider landscape beyond these two, see its guide to the best AI guest messaging tools for Airbnb in 2026. FAQ. Is StayReply a good HostReply alternative? It depends on your PMS and portfolio size. StayReply connects to a broader list of PMSs (Hostaway, Guesty, Hospitable, and others) and scales its per-property price down at high volume, which suits a large, PMS-diverse portfolio. HostReply integrates more deeply with a smaller set of PMSs (Hospitable and OwnerRez) at a flat, size-independent price, which suits hosts on either of those two systems who want live lookups instead of a curated knowledge base. Does StayReply cost more or less than HostReply? It depends on portfolio size. StayReply's published pricing starts at $29/property/month for 1-10 properties and steps down to $19/property/month around 76-250 properties. HostReply is a flat $19/property/month regardless of size, so small portfolios generally pay less with HostReply, while very large portfolios can reach a comparable per-property rate with StayReply's top volume tier. Which PMSs does each tool connect to? HostReply integrates live with Hospitable and OwnerRez today, with Hostaway and Guesty coming soon. StayReply connects through a broader list - Hostaway, Guesty, Hospitable, and, per its own marketing, "14+" supported systems. How does each tool decide when to escalate to the host? Both use a confidence-based model: you set how confident the AI needs to be before it auto-sends a reply, and anything below that line escalates. HostReply escalates by SMS with a one-line summary and a draft you can edit or send as-is. StayReply also flags sensitive categories like complaints, refund requests, and emergencies for review, though its own materials don't publicly document which notification channel it uses to reach you. Ready to try HostReply? Start your 14-day free trial today. No credit card required. See how tool-based AI messaging with SMS escalation works for your properties.

BetterSTR
Jul 22nd, 2026
BetterSTR now integrates with Hospitable.

BetterSTR now integrates with Hospitable. Its first PMS integration is live - and it's a big one. BetterSTR is now an official partner in the Hospitable App Marketplace: connect in one click and every listing and reservation syncs automatically. Today's a milestone day for BetterSTR. BetterSTR is now listed in the Hospitable App Marketplace as an official partner using Hospitable's APIs - its first property management software integration, and the easiest way yet to give every one of your guests a personalised digital guidebook. Like everything at BetterSTR, it's free. If you run your Airbnb, Vrbo, Booking.com or direct bookings through Hospitable, you don't even need to sign up on its site first. Connect from inside Hospitable and your BetterSTR account is created automatically, with your listings and reservations already synced. What actually syncs. * Listings: your properties come across with the details BetterSTR needs to build a guidebook that already knows your place. * Reservations: guest names, stay dates and the channel the booking came from - kept in sync automatically as bookings are created, changed or cancelled. Every reservation gets its own guidebook link. The moment a reservation syncs, BetterSTR generates a unique guest guidebook link for that stay - personalised to that guest, that property and those dates, with their actual check-in and check-out times. Drop the link into your Hospitable message templates once, and every future guest gets their own guide without you lifting a finger. Inside the guide: your house rules, WiFi details, appliance instructions, local recommendations and anything else you'd normally answer over and over in messages - beautifully presented, opening in any browser, with no app for guests to download. How to connect (about one minute). * Log in to Hospitable and click Apps in the left-hand menu. * Under Integrations, click Guestbook, then BetterSTR. * Click Get Started. Your BetterSTR account is created automatically and your listings and reservations sync straight away. Common questions. Does this cost anything? No. The BetterSTR digital guidebook is free, and so is the Hospitable connection. Do I need a BetterSTR account first? No - connecting from the Hospitable App Marketplace creates your account automatically. No signup forms. Do guests need to download an app? No. Guidebook links open in any browser, and the unique per-reservation link is generated automatically for every booking that syncs from Hospitable. Which booking channels does it cover? Whatever flows through your Hospitable account - Airbnb, Vrbo, Booking.com and direct bookings all sync across with their reservations. Want the full feature rundown? See the Hospitable integration page, or learn more about BetterSTR digital guidebooks. Running on Hospitable? Open the App Marketplace, click Guestbook | BetterSTR, and your guests get personalised guidebooks tonight. Or create a free account first.