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 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.

• 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

• 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

• 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

• 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

What You Can Expect From 2020 Companies

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.