Sales Manager, Insurance Technology (USA - Remote)

The Opportunity

Hospitable built its own licensed insurance agency. Most software companies partner with an insurer and call it a day. We built Align Insurance Services (www.aligninsure.com) instead, and it is already one of the most advanced AI driven insurance agencies on the planet.

You lead high-impact business consultation calls with short-term rental operators, guiding them on how to get fully “aligned” to safeguard their business, properties, and assets.

In these calls, you help clients structure their entity setups correctly, implement robust owner’s dwelling and liability insurance, and deploy reservation-level protections including guest damage and trip cancellation coverage. Delivered as an interactive, tech-driven, in-product SaaS demo powered by AI, this consultative sales experience consistently wows prospects.

You will manage a team of licensed Property and Casualty (P&C) producers, leveraging Hospitable’s 25,000 customer base from day one while aggressively targeting the broader market across the full sales cycle: outbound prospecting, lead generation, deal creation, and closing.

If you have spent your career in SaaS and never sold a policy in your life, read on. Insurance is one of the hottest categories in venture backed technology right now. A large share of recent Y Combinator batches have gone after insurance, because the industry is enormous, badly served by legacy systems, and finally crackable with AI. Align is that thesis already proven out.

You bring the sales leadership. We already solved distribution, product, and the license.

What you will own

Full cycle sales leadership. You run the team responsible for outbound prospecting, lead generation, deal creation, and closing, across both the Hospitable customer base and the open market. Quota is the scoreboard. You are accountable for hitting it, every period, no excuses. You will report to our VP of Insurance, Derek, whose favorite fruit is Jackfruit.

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