Sales Leadership - Insurance (Align Insurance Services)

Hospitable built its own licensed insurance agency, Align Insurance Services, which is already one of the most advanced AI-driven insurance agencies globally.

You will lead high-impact business consultation calls with short-term rental operators, guiding them on safeguarding their business, properties, and assets. These calls involve structuring entity setups, implementing robust owner’s dwelling and liability insurance, and deploying reservation-level protections like guest damage and trip cancellation coverage. Delivered as an interactive, tech-driven, in-product SaaS demo powered by AI, this consultative sales experience consistently impresses 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 but never sold a policy, this opportunity is for you. Insurance is one of the hottest categories in venture-backed technology right now. A significant share of recent Y Combinator batches have focused on insurance due to its massive size, poor service from legacy systems, and potential for disruption with AI. Align has already proven this thesis. You bring the sales leadership; we’ve already solved distribution, product, and licensing.

What You Will Own

You will oversee full-cycle sales leadership, running 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, and you are accountable for hitting it every period. You will report to our VP of Insurance, Derek.

You will engage in daily coaching, actively participating in deals with your reps rather than reviewing them afterward. Your goal is to sharpen the team weekly and build a culture where reps continuously improve their sales craft.

You will manage the property protection dashboard, a core feature of Hospitable’s product that helps operators configure the right layers of coverage. Your team will assist 25,000 customers in using it correctly, starting with basic entity setup and layering best practices to protect businesses and properties.

Align operates as a broker, offering objective recommendations across the market while also having its own insurance products. You will teach your team to balance these two truths: selling what is right for the customer and knowing when Align’s own product is the best fit.

You will be responsible for hiring and team building, recruiting and hiring internally, and managing third-party labor arrangements. Your focus is on building a bench, not just filling seats.

You will design and run commission programs that keep producers motivated and performing, owning the results these programs produce.

You will build a sales culture that excites reps to be part of it, fostering real career growth within your team or elsewhere in Hospitable.

Requirements

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

We prioritize a great sales leader with enthusiasm for technology and software. Insurance experience is a plus but not mandatory. We prefer someone who can lead a modern, AI-powered sales organization over an insurance veteran who lacks leadership experience.

• 5+ years of sales leadership experience, ideally running quota-carrying teams through full sales cycles, from outbound and lead generation through closing, not just account management.
• Genuine passion for technology and software, not just tolerance for it. You should want to sell through a platform, use AI tools daily, and understand how technology transforms sales organizations.
• A proven track record of hiring, developing, and retaining sales talent.
• Comfort designing and running commission plans that effectively motivate behavior rather than just paying out.
• Insurance or P&C background is a plus but not required. Hospitable will sponsor you to obtain a license if you don’t already have one.

Why Insurance, Why Now

Insurance is no longer a boring, legacy category. It is one of the most targeted sectors by venture capital over the last several years. The market is massive, incumbents rely on outdated infrastructure, and AI can finally address underwriting, claims, and distribution challenges that have slowed the industry. The founders and investors pursuing this thesis are correct: insurance is one of the biggest, most fixable markets in tech right now.

Align is the embodiment of this thesis—already built, selling, and profitable—inside a company that doesn’t need to raise capital to prove its success.

Why Hospitable, Why Now

Hospitable operates at a $50M+ ARR run rate, growing 100% year over year, with no venture capital or private equity funding. This means no board meetings or investor management—just a company fully in control of its destiny, free to reinvest in product and people.

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

Benefits

• A supportive, radically transparent, and caring team environment, where you are trusted, not managed—and a culture focused on results and output.
• The gross salary for US employees ranges between USD $106,044.87 - $133,893.17, with a 10% seniority increase after 6 months if performance standards are met.
• Eligibility for commission, with the OTE to be discussed directly with candidates.
• Compensation through company equity via RSUs, 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, including self-served public holidays and parental leave.
• Complimentary mental health and emotional support with therapists available through Slack via Spill.
• Earn virtual coins through our peer recognition platform and redeem them for gift cards, donations, or monetary rewards.