Operations Manager, R&D Operations & AI Enablement

Who is Whip Around?

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.

Why this role is important to us:

Reporting to the Director of Operations, the Operations Manager helps improve our internal AI tools and agents while supporting our R&D and Engineering teams with operational measurement, analytics and reporting. Working closely with the Director of Operations and our technical teams, this role helps investigate, implement, validate and continuously improve internal AI solutions, while supporting the data, systems and processes that keep them accurate and reliable.

A key part of the role is supporting Whip Around’s AI enablement efforts across customer-facing teams. 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 solutions, and embed those tools into everyday workflows to save time and improve consistency. We’re looking for someone with hands-on experience helping teams put AI into practical use, improve the quality and reliability of AI-assisted workflows, and demonstrate measurable value from the solutions they implement.

What success looks like:

Operational Delivery & Support

•     Support the Director of Operations in keeping workflows, resources and projects on track and aligned to team goals and developing initiatives.

•     Track and report on operational KPIs against targets set with the Director, flagging performance gaps and helping put corrective action in place.

•     Help manage operational budgets, systems and vendors to ensure we receive appropriate value from our investments.

•     Identify new opportunities for AI within assigned areas of responsibility and help design and implement practical solutions..

AI Enablement & Use-Case Delivery

•     Support the rollout and adoption of AI and automation tools across the team, providing guides, training and hands-on support people need to use them confidently and effectively.

•     Help identify and prioritize practical AI use cases tied to clear outcomes — reducing manual effort, improving consistency and saving time or cost.

•     Deliver early, practical “quick wins” in the first few months, then help establish repeatable processes for monitoring evaluating and improving solutions already in use..

•     Help ensure live AI tools and agents have access to accurate, current and appropriate information so they remain reliable and trusted by the people using them.

•     Maintain clear communication with stakeholders across the business to ensure AI agents and workflows remain aligned with current data, processes and organizational changes.

Process Improvement & Systems

•     Map and improve core operational processes, identifying bottlenecks where automation or AI could reduce manual administration and sharing recommendations with the Director.

•     Support R&D and Engineering AI initiatives and help teams improve reporting and data quality.

•     Document processes, tools and standard operating procedures so that knowledge is captured, repeatable and easy for the team to follow.

•     Manage and monitor new system integrations and coordinate new AI agent requests and intake as they arise.

Data, Reporting & Stakeholder Support

•     Help develop and maintain meaningful R&D and Engineering metrics and reporting, using data from development and work-management systems to provide visibility into delivery, capacity, workflow health and operational trends.

•     Build strong relationships with R&D and engineering to develop a deep understanding of their of their workflows, needs and challenges, and help design AI-assisted reporting that provides useful operational insights while supporting broader company reporting requirements.

•     Conduct regular a…