Operations Manager, Customer Success & AI Enablement

Whip Around is an award-winning, easy-to-use fleet maintenance software company that connects drivers, mechanics, and fleet managers to improve the uptime of vehicles and equipment. Founded in 2016 and headquartered in San Diego, CA, we’re on a mission to keep the world’s fleets moving.

Team culture is at the heart of our success, with personal improvement being just as important as company outcomes. We boast a senior leadership team with experience from numerous successful global businesses, and we continue to double down on our vision to bring simplicity and efficiency to fleet management and compliance — increasingly powered by data and artificial intelligence.

Reporting to the Director of Operations, the Operations Manager helps keep our AI tools and Customer Success systems running smoothly and efficiently. Working closely with the Director, this role supports AI development and accuracy, maintains integrations and Customer Success tools, and strengthens the AI models that our teams depend on to continue growing the reliability and usage of AI in our business and to support our ability to scale. This role also supports the systems that drive our AI models.

A key part of the role is supporting Whip Around’s AI enablement efforts for Customer Success. Under the direction of the Director of Operations, the Operations Manager will help identify practical opportunities for AI and automation, turn promising experiments into reliable, repeatable use