Founding Sales Executive

Job Title: Founding Software Sales Executive

Company: OrangeAI

Location: Naples, FL (Hybrid / On-site base with heavy regional travel)

Job Type: Full-time

About OrangeAI

OrangeAI is a fast-growing, early-stage AI startup building the next generation of intelligent automation and management software for the insurance industry. We are rewriting the playbook on how agencies operate, replacing legacy friction with streamlined, AI-driven workflows. The product “Orange Julius” is being designed from within our highly successful insurance agency- Harbour Insurance. It is designed by insurance agents and for insurance agents to fit a specific need for insurance agents to become “agentic”.

We have built an Agentic AMS system that will replace legacy AMS systems .—you will be helping establish our sales playbook, defining our market presence, and directly impacting the trajectory of the company. If you are a high-energy hunter who thrives in a fast-paced startup environment and loves being out in the field, we want you on the ground floor.

The Role

We are looking for a dynamic, results-driven Software Sales Account Executive to spearhead our outward growth. In this role, you will own the entire sales cycle—from prospecting and running high-impact demos to negotiating contracts and closing new business.

Note on Travel: This is a high-visibility, field-facing role. You will spend significant time on the road building face-to-face relationships, including a heavy travel schedule visiting insurance agencies across Florida and representing OrangeAI at 6+ industry conventions and trade shows per year.

What You’ll Do

• Own the Pipeline: Prospect, qualify, and build a robust pipeline of net-new business opportunities through strategic outbound outreach and in-person agency visits.
• Hit the Road: Travel extensively throughout Florida to meet with agency principals, build localized trust, and deliver high-impact, face-to-face product demonstrations.
• Own the Convention Floor: Prepare for, attend, and maximize leads at 6+ major insurance technology and industry conventions annually, driving brand awareness and unlocking enterprise opportunities.
• Run the Full Cycle: Conduct discovery to understand agency pain points, navigate decision-making processes, overcome objections, and consistently close deals.
• Collaborate with Product: Act as the voice of the market. Gather real-world feedback from the field and collaborate directly with our engineering and founding teams to shape our product roadmap.

What We’re Looking For

• Experience: 2+ years of B2B SaaS or field sales experience (closing experience preferred). Experience or deep familiarity with the insurance space (Agencies, CRMs, or AMS platforms) is a massive plus.
• The Ultimate Plus: Former Insurance Marketing Representatives with an established book of contacts in Florida. If Sunshine State agency owners already know, like, and trust you, you are our ideal candidate.
• Willingness to Travel: Comfort and excitement around a heavy travel schedule (both regional road travel in Florida and national convention travel).
• The Startup Mindset: A self-starter who embraces ambiguity, moves fast, and thrives in an autonomous field environment.
• Exceptional Communication: You are an active listener who can command a room, whether it's a local agency boardroom or a crowded convention floor.
• Proven Track Record: A history of hunting down new business and consistently hitting or exceeding quota.

What We Offer

• Competitive base salary + uncapped commission structure.
• Comprehensive travel expense reimbursement / mileage allocation.
• Early-stage equity options (own a piece of what you build).
• Direct access to leadership and rapid career acceleration opportunities as the sales team expands.
• High-energy, collaborative office culture in beautiful Naples, FL, to return to between trips.

Compensation Package

· Compensation: $70,000 - Base Salary + Uncapped Commission (Year 1 $30,00 -$50,000)

· Early-Stage Equity: Performance-based stock options for founding team members- 1%

· Travel & Expense: 100% covered travel expenses, car mileage, lodging, per-diem, and convention entry fees.

How to Apply

If you are ready to leverage your existing industry relationships, hit the road, and help scale a disruptive tech startup from the ground up, submit your resume and a brief note on why you’re the right fit for the founding sales team at OrangeAI. Email Will Kastroll View email address on click.appcast.io and tell me specially why your have “What we are looking for”. 

This wont be easy and only apply if you want one of the hardest sales challenges in your life that if you are successful will put you on the forefront of AI technology and you will make a lot of money. If you want a mail in, cushy sales job – this is not for you. Excellence is earned.