Remote AI-Driven Insurance Sales Leader

Hospitable, Inc.; Northern (KY); Hybrid; USD 106,000 - 134,000; Full time

Benefits offered by this job

Commission plans

Equity (RSUs)

Healthcare

401(k)

35 days off per year

Job summary

Hospitable seeks a proven sales leader to run outbound prospecting, lead generation, deal creation, and closing across both the Hospitable customer base and the open market. You’ll own quota and coach daily, building a high-performance team in a remote, AI-driven SaaS environment.

You’ll shape commission programs, hire and develop talent, and leverage Align Insurance Services to offer both broker recommendations and Hospitable’s own products. Insurance background is a plus but not required.

Qualifications

• 5+ years of sales leadership driving quota-attainment across full sales cycles (outbound, lead gen, deal creation, close).
• Genuine enthusiasm for technology and software; ability to leverage AI tools daily.
• Track record of hiring, developing, and retaining sales talent.
• Comfort designing and running commission plans that motivate behavior.
• Insurance or P&C background is a plus, not required; sponsor possible after start.

Responsibilities

• Lead outbound prospecting, lead generation, deal creation and closing across Hospitable's base and open market.
• Coach daily with reps to sharpen performance and build a high-output culture.
• Own the property protection dashboard and ensure customers configure appropriate coverages.
• Balance broker integrity with proprietary products and teach when to recommend Align's products.
• Hire, develop, and manage internal staff and external labor; design compelling commission programs.

Skills

Sales leadership

Tech enthusiasm

Talent development

Commission design

Insurance background (plus)

Job description

Hospitable seeks a proven sales leader to run outbound prospecting, lead generation, deal creation, and closing across both the Hospitable customer base and the open market. You’ll own quota and coach daily, building a high-performance team in a remote, AI-driven SaaS environment.

You’ll shape commission programs, hire and develop talent, and leverage Align Insurance Services to offer both broker recommendations and Hospitable’s own products. Insurance background is a plus but not required.