OrangeAI's Customer Experience / Success (CS)

OrangeAI

Customer Success Specialist

Naples, FL | Full-time | In office 3 days a week

We are looking for a Customer Success (CS) teammate to onboard, nurture and create relationships with our clients. Your job is to create “Raving Fans” of our product with our customers. Our customers want and deserve this technology. If you want to be a part of a fast-growing company, gain invaluable experience, have the ability to move up in the company and at the end of the day feel like you are adding value to a team, then this role may be right for you.

About OrangeAI

OrangeAI is an AI-native Agency Management System (AMS) built for independent insurance agencies, by independent insurance agents. Our platform streamlines agency workflows, automates modern communication, and puts agentic AI to work on the clicking and keystroking that eats up an agent’s day, so agents can get back to advising their clients. We are growing quickly and looking for a customer-obsessed professional to help build our support and success operations from the ground up.

The Role

As our Customer Success teammate, you will be the heart of OrangeAI’s customer-first culture. You will bridge the gap between traditional insurance practices and modern AI-powered software. Your goal is to guide insurance agencies through successful transitions to OrangeAI, ensuring high retention, smooth onboarding, and consistent product adoption.

Key Responsibilities

• Drive Successful Onboarding: Own the customer journey from post-sales handoff through go-live and initial training. Coordinate the agency side of data conversions with our engineering team, keeping the customer informed and confident throughout.
• Be the First Line of Support: Serve as the main contact for platform issues. Troubleshoot, resolve what you can, and escalate confirmed bugs to engineering with clear steps to reproduce.
• Triage With Agency Impact in Mind: Sort every issue as a bug, a product gap or a training need before it goes to engineering. Anything touching a renewal, a policy, a client record or money gets handled first.
• Run Quarterly Agency Reviews: Meet with each agency every quarter to learn how their experience is going, review their usage and adoption, and plan goals for the next quarter.
• Cultivate Long-Term Success: Monitor agency usage to proactively prevent churn, identify accounts at risk, and uncover expansion opportunities.
• Serve as an Insurtech Advisor: Understand the unique workflows of insurance agents and guide them on how to get the most out of OrangeAI in their day-to-day operations.
• Champion the Customer Voice: Partner closely with Product and Engineering, turning customer feedback into clear input for our product roadmap.
• Create Self-Service Resources: Build and maintain training materials, video tutorials and our knowledge base, including the FAQ answers Julius gives users. When the product changes, you keep the answers current.

What We’re Looking For

• AI Native: Our company is an AI company and you have to be on the front end of AI in use and function. You use AI every day to do real work, not just to chat with it.
• Experience: 2 years in a customer-facing SaaS role such as customer support, customer success or implementation. We can train you on “insurance” and “insurance agencies.”
• Communication Skills: Exceptional empathy and communication skills, with the ability to explain technical and AI concepts to traditional business owners.
• Growth Mindset: Thrives in a fast-paced, fluid startup environment where building processes from scratch is part of the fun.
• Unstoppable: Every teammate we have views themselves as “unstoppable.” A hurdle is just a data point.
• A Good Person: We all live by the “Golden Rule.” How you want to be treated is how you treat others. We spend so much time together and want to be around good people.

Technical Aptitude

• Uses AI tools daily and effectively: You use tools like Claude or ChatGPT every day to draft, research, troubleshoot and summarize. Be ready to show us how you work with them.
• Comfortable with connected AI tools (MCPs): You understand how AI assistants connect to platforms like Sentry, Klaviyo and Resend, and can use them to investigate on your own, such as pulling the error behind a user’s complaint or confirming whether an email was delivered.
• Investigates before escalating: You check logs, reproduce the issue and narrow it down before anything reaches engineering. Escalations arrive with exact steps, screenshots or a recording, and what you already ruled out.
• Bonus: Basic SQL or API familiarity, or experience writing help documentation or training an AI assistant on it.

Location

One of the big advantages of OrangeAI is that you will be working INSIDE an active insurance agency (Harbour Insurance) where we build, test and update the platform. Every day you will be working in a real sandbox building the next generation of insurance agency management software while getting direct feedback from insurance agents and customers.

We are based in a fast-growing state, Florida, and a great town, Naples. We don’t mind some remote work, but being in the office of an active insurance agency is a must. 3 days a week in the office is required.

Travel

We attend a lot of insurance agency conventions. Our sales team covers these, but it is always valuable to have our CS teammate at a few of them each year.

Compensation

$60,000 base salary plus an annual bonus of up to $10,000.

How to Apply

You have to have the technical ability listed above if you do Send your resume and a short note about why this role fits you to wkastroll@hrm.us

Pay: $60,000.00 per year

Work Location: In person

Salary : $10,000 - $60,000