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.

Requirements

Hospitable is a remote-only and globally distributed company but for this role, we need someone who is based in the United States.

We want a great sales leader first. Insurance experience is a real plus, but it is not the gate. Plenty of the best SaaS sales leaders have never sold a policy in their life, and we would rather hire that person and teach them insurance than hire an insurance lifer who cannot lead a modern, AI powered sales org.

• 5+ years of sales leadership experience, ideally running quota carrying teams through full sales cycles, from outbound and lead generation through close, not just account management
• Genuine enthusiasm for technology and software, not tolerance of it. You want to sell through a platform, use AI tools daily, and think about how technology changes what a sales org can do
• A track record of hiring, developing, and retaining sales talent
• Comfort designing and running commission plans that actually motivate behavior instead of just paying out
• Insurance or P&C background is a plus, not a requirement. If you have never held a P&C license, Hospitable will sponsor you to get one after you start

Why Insurance, Why Now

Insurance is not a boring, legacy category anymore. It is one of the categories venture capital has chased hardest over the last several years, and a large share of recent Y Combinator batches have built insurance companies, because the market is massive, the incumbents run on decades old infrastructure, and AI can finally attack the underwriting, claims, and distribution problems that made the industry slow in the first place. The founders and investors chasing that thesis are not wrong. Insurance is one of the biggest, most fixable markets in tech right now.

Align is that thesis, already built, already selling, already profitable, inside a company that does not need to raise a round to prove it out.

Why Hospitable, Why Now

Hospitable is running at a $50M+ ARR run rate, growing 100% year over year, with no VC or PE money in the business. That means no board meetings to prepare for and no investors to manage, just a company in full control of its own destiny, free to reinvest in the product and the people building it.

Align is the boldest expression of that: a licensed insurance agency built by a software company, with an AI first approach that traditional agencies and most insurtech startups cannot match, and a 25,000 customer pipeline that most insurance sales leaders would need years to build from scratch, and that most insurtech startups would need a huge funding round to buy.

Benefits

The company itself is also a product, one that we iterate on. We're always improving and creating an environment where we all love to work.

• A supportive, radically transparent, and caring team environment, where you are trusted, not managed—and a culture that is focused on results and output.
• The gross salary for US employees could be anywhere between USD$106,044.87 - $133,893.17, with a 10% seniority increase after 6 months provided performance standards are met.
• On top of the base salary, this role is also eligible for commission, with the OTE to be discussed directly with candidates.
• We also offer compensation into the company equity through (RSU's), with a current grant value of up to $59,400.00 to share in the long-term upside value of the company.
• For US employees: healthcare (including EPO, PPO and HSA), 401(k).
• 35 days off per year, encouraged (including self-serve public holidays) and parental leave.
• Complimentary mental health and emotional support with therapists on call through Slack by Spill.
• Earn virtual coins through our peer recognition platform and redeem them through gift cards, donations, or monetary rewards.