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.

Daily coaching. You are in the deals with your reps, not reviewing them after the fact. You coach daily so the team gets sharper every week, and you build a culture where people want to get better at the craft of selling.

The property protection dashboard. Hospitable's core product includes a property protection dashboard that helps operators configure the right layers of coverage. Your team helps 25,000 customers use it correctly, starting with the most basic layer of protection there is: getting their business entities set up right, then layering the best practices to help hosts protect their business and property. 

Broker integrity plus proprietary product . Align operates as a broker, so your team brings customers objective recommendations across the market. Align also has its own insurance products. You teach your team to hold both truths at once: sell what is right for the customer, and know when that is Align's own product.

Hiring and team building . You recruit and hire internally, and you manage third party labor arrangements alongside that. You are building a bench, not just filling seats.

Commission programs . You design and run the compensation structures that keep producers motivated and performing, and you own the results those programs produce.

Culture . You build a sales floor people are excited to be part of, one where reps are building real careers, whether that means growing inside your team or moving anywhere else within Hospitable.