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 cases, and embed those tools into everyday workflows to save time and improve consistency. We’re looking for someone who has hands-on experience improving Customer Success outcomes by transforming AI use cases into real-world use and can show the value they delivered.

What success looks like

Operational Delivery & Support

• Manage day-to-day operations within the Customer Success tools, supporting the Director of Operations to keep workflows, resources and projects on track and aligned to team goals.
• 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 and tools, keeping an eye on spend and making sure we get good value from our systems and vendors.

AI Enablement & Use-Case Production

• Support the rollout and adoption of AI and automation tools across the team, providing guides, training and hands-on help people need to use them confidently.
• Help identify and prioritize practical AI use cases tied to clear outcomes — reducing manual effort, improving consistency and saving time or cost.
• Take promising experiments through to reliable, repeatable use cases: gathering requirements, validating outputs, supporting rollout, and maintaining, updating and improving the tools once they’re live.
• Deliver early, practical “quick wins” in the first few months, then help establish simple routines for monitoring and improving the solutions in use.
• Keep live AI tools fed with accurate, current information so they stay reliable and trusted by the people using them.

Process Improvement & Systems

• Map and improve core operational processes, spotting bottlenecks where automation or AI could replace manual administration and sharing recommendations with the Director.
• Help maintain and improve core systems (e.g., Salesforce, Hubspot, Jira, Mixmax), and flag integration gaps or usability issues in the tech stack.
• 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 for the Customer Success team as they arise.

Data, Reporting & Stakeholder Support

• Gather data needs from teams across the business and turn them into clear reports, dashboards and useful insights.
• Run regular audits of key business data to ensure accuracy, and work with teams to find and resolve sources of variance.
• Help prepare monthly and quarterly analytics for the Director and senior leadership, explaining findings clearly to both technical and non-technical audiences.

Collaboration & Team Support

• Work closely with the Director of Operations and partner with Sales, Customer Success, Finance and Product Operations to keep work coordinated across teams.
• Bring structure, timelines and follow-through to operational projects so they stay on track.
• Provide documentation, support and training for internal users.

Compliance & Quality

• Follow and help maintain responsible-use, data privacy and quality controls for AI and automation, so the tools we use stay safe and trustworthy.
• Support compliance with applicable data privacy regulations and partner with the Tech team on security where needed.
• Flag operational risks early and perform other duties as assigned to support projects and departmental needs.

What you’ll bring to the role

Critical Competencies

• Customer Success Agentic Strategy & Delivery
• Partner with business stakeholders to identify, prioritize, prototype, and implement high-impact automation and AI opportunities for the Customer Success team.
• Drive adoption of AI solutions through training, documentation, and continuous improvement based on user feedback.
• AI Engineering & Operations
• Model evaluation and performance monitoring
• AI observability and quality assurance
• Managing hallucination risk and response accuracy
• Prompt optimization and, where appropriate, model fine-tuning, and guardrails
• Familiarity with data validation frameworks or QA checkpoints to catch bad or incomplete data before it reaches a production AI workflow
• Evaluate emerging AI models, tools, and techniques, and recommending pragmatic adoption where they can provide measurable business value.
• Salesforce & Customer Success Systems Engineering & Administration
• Strong hands-o