Sales Manager, Insurance Technology (USA - Remote)

About this role

Lead the sales team for Align Insurance Services, Hospitable’s licensed insurance agency, selling insurance solutions to short-term rental operators. Own the full sales cycle, team performance, coaching, hiring, and commission programs. The role combines consultative sales with a technology- and AI-driven platform.

About the company

Hospitable builds software for short-term rental hosts and property managers to automate listings, messaging, and operations across booking platforms.

What you'll do

• Lead the team’s outbound prospecting, lead generation, deal creation, and closing across Hospitable customers and the broader market
• Own sales quotas and team results
• Coach sales representatives daily and develop their selling skills
• Help customers configure property protection and insurance coverage
• Train the team to make objective broker recommendations while identifying when Align products fit
• Recruit, hire, and manage internal and third-party sales staff
• Design and manage commission programs

What we're looking for

• 5+ years of sales leadership experience, ideally leading quota-carrying teams through full sales cycles
• Genuine enthusiasm for technology, software, and using AI tools
• Track record of hiring, developing, and retaining sales talent
• Experience designing and managing motivating commission plans
• Must be based in the United States

Nice to have

• Insurance or Property and Casualty (P&C) experience
• P&C license; the company will sponsor licensing after hire if needed

Benefits

• Base salary of $106,044.87–$133,893.17 per year
• 10% seniority increase after 6 months if performance standards are met
• Commission eligibility; OTE discussed with candidates
• RSU grant with a current value of up to $59,400
• Healthcare options including EPO, PPO, and HSA, plus 401(k)
• 35 days off per year and parental leave
• Access to mental health and emotional support