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-on Salesforce administration experience, equivalent to Salesforce Administrator certification-level knowledge or higher. • Ability to configure, build, test, and maintain Salesforce solutions based on defined business requirements and architectural direction. • Experience with Salesforce configuration including custom objects and fields, Lightning pages, permissions and security, Flow automation, validation rules, reporting, dashboards, data management, and general platform administration. • Experience integrating Salesforce with Customer Success platforms and other business systems, including supporting data mapping, synchronization, process design, testing, and troubleshooting. • Experience implementing, configuring, or significantly expanding Customer Success applications and workflows to support Customer Success teams and processes. • Ability to translate operational requirements into practical, scalable system solutions and identify when an existing process or configuration can be improved rather than simply reproducing the current state. • Strong troubleshooting skills and comfort investigating issues across multiple systems, integrations, automations, and data sources. • Comfortable learning and administering multiple platforms, evaluating new functionality, and bringing forward recommendations for improving existing systems and processes. • Able to work independently from high-level technical or process direction — taking a defined outcome or proposed approach and carrying it through configuration, testing, documentation, deployment, and ongoing support. • Comfortable balancing project-based system development with day-to-day Salesforce and Customer Success platform administration and support. Professional Skills • Well organized and dependable, with the ability to manage multiple priorities, work independently, and bring structure to ambiguity. • Strong analytical and problem-solving skills, with a genuine interest in identifying patterns, understanding root causes, and developing practical solutions. • Excellent interpersonal and written communication skills, with the ability to build strong, supportive working relationships across technical and non-technical teams. • Able to communicate complex technical concepts clearly and document system design, configuration, decisions, and dependencies in a way that supports shared ownership and future maintenance. • Comfortable working from defined architectural direction while independently determining and executing the detailed steps required to deliver a solution. • Collaborative approach to systems development, including actively seeking peer review, incorporating feedback, communicating proposed changes, and recognizing architecture as a shared responsibility rather than an individual domain. • Ability to design solutions with maintainability, extensibility, and future change in mind, avoiding unnecessarily rigid implementations and considering downstream impacts, integrations, and eventual system transition or replacement. • Strong attention to detail, accuracy, and data integrity, with a high level of professional accountability. • Experience with process improvement and project coordination, including managing dependencies and communicating progress, risks, and changes. • Solid working understanding of data and metadata, including data auditing, cleansing, visualization, transformation, and manipulation. • Comfortable working in a fast-moving, growing environment where requirements evolve and solutions may need to adapt quickly, with a bias toward practical and measurable results. • Receptive to feedback and willing to challenge or refine an approach constructively while remaining aligned with agreed technical standards, architecture, and team decisions. Preferred and Differentiated Competencies: • Experience with enterprise security, governance, privacy, compliance, and access-control practices. • Familiarity with Git, source control, deployment practices, and software engineering principles that support maintainable, reviewable system development. • Experience with API-based integrations, including REST/SOAP concepts, authentication, data mapping, error handling, and troubleshooting across connected systems. • Working knowledge of Salesforce development technologies, including SOQL, SOSL, Apex, and Lightning Web Components. • Experience working with relational databases such as Microsoft SQL Server or PostgreSQL, including querying, data validation, and troubleshooting. • Strong proficiency with Microsoft Excel, including advanced formulas and data manipulation; experience with BI and visualization tools such as Tableau or Power BI is a plus. • Prior experience implementing, configuring, migrating, or redesigning Customer Success platforms or related business applications. • Experience supporting system integrations, platform migrations, or application transitions, including consideration for data continuity, dependencies, documentation, and maintainability. • Previous experience working in SaaS, Customer Success, Revenue Operations, Business Systems, or a similar technology-driven environment. • Exposure to release management, testing practices, technical documentation, and peer review processes within a shared systems environment. • Experience evaluating new tools or platform capabilities with consideration for integration requirements, long-term maintainability, scalability, and total operational impact. Experience & Qualifications: • Bachelor’s degree in Business Information Systems, Operations Management, Analytics, Computer Science, or a related field, or equivalent practical experience. • 5+ years of hands-on experience in Salesforce administration, business systems, Customer or Revenue Operations, automation, data, or a related technical operations role. • Demonstrated experience administering and improving production Salesforce environments, including automation, data management, security and permissions, reporting, integrations, troubleshooting, and ongoing user support. • Experience owning or contributing substantially to system implementations, integrations, migrations, or significant platform changes from requirements gathering through testing, deployment, documentation, and ongoing support. • Hands-on experience delivering automation or AI solutions for real-world business workflows, with experience designing, building, or deploying generative AI or agentic solutions strongly preferred. Location & Work Arrangement · Location: Remote, with preference in US Central or Eastern time zones · Hours: Full-time. Occasional early or late calls to overlap with New Zealand colleagues. · Travel: Minimal. Compensation : $105K - $125K USD, depending upon experience and location Unlimited PTO: Use your paid time off when you need it Subsidized Healthcare : A variety of subsidized medical plans to fit your needs Retirement Support: 401(k) matching to help you invest in your future. Family Friendly: Paid parental leave and caregiver support Growth & Development: Professional development plans and resources to support continuous learning. Even if you don’t meet every single requirement, we encourage you to apply