Operations Manager, R&D Operations & AI Enablement

Summary

Whip Around is a fleet maintenance software company that connects drivers, mechanics, and fleet managers to improve vehicle and equipment uptime. The Operations Manager will support R&D and Engineering operations through AI enablement, operational analytics, reporting, process improvement, and systems coordination. The role will help implement reliable AI-assisted workflows, improve data quality, and support cross-functional teams in achieving measurable operational outcomes.

Responsibilities

• 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
• 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
• 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
• 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 audits of key business data and operational data to ensure accuracy , working with relevant teams to identify and resolve sources of variance
• Help prepare monthly and quarterly analytics for the Director and senior leadership, communicating findings clearly to both technical and non-technical audiences
• Work closely with the Director of Operations and partner with other Operations Managers 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
• 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
• Identify and escalate operational risks early and perform other duties as assigned to support projects and departmental needs

Skills

• Comfortable working with structured business and operational data using SQL, spreadsheets, reporting platforms, or BI tools
• Hands-on experience using generative AI tools to solve business or operational problems
• Experience building, configuring, training, testing, and refining AI agents or AI-assisted workflows
• Strong working knowledge of Claude and the ability to build and iteratively improve Claude-based projects, agents, workflows, or other AI solutions
• Ability to evaluate AI-generated outputs for accuracy, usefulness, consistency, and appropriate use of source context
• Experience improving AI performance through prompt design, instructions, context management, source-data refinement, testing, and feedback
• Understanding of hallucination risk and practical approaches for improving the reliability of AI-generated outputs
• Experience designing AI workflows that incorporate human review or approval where appropriate
• Ability to identify practical opportunities where AI can reduce manual work, improve reporting, surface useful insights, or support better decision-making
• Comfortable experimenting with new AI capabilities and determining whether they provide meaningful business value
• Experience working closely with software engineering, product, technical, or R&D teams
• Ability to translate between technical and non-technical stakeholders and turn business needs into clear requirements, workflows, reporting, or process improvements
• Strong stakeholder-management skills, including the ability to influence, coordinate, and move work forward without direct authority
• Comfortable asking technical teams for information, clarification, or assistance while respecting competing priorities and engineering ownership
• Able to independently investigate problems, gather available context, and clearly define what assistance is needed before escalating to Engineering
• Comfortable operating as a collaborative peer within a technical environment rather than as a people manager
• Well organized and dependable, with the ability to manage multiple priorities and bring structure to ambiguous problems
• Excellent interpersonal and written communication skills, with the ability to build productive working relationships across technical and business teams
• Able to communicate technical concepts and analytical findings clearly to both technical and non-technical audiences
• High level of integrity, attention to detail, and accuracy
• Curious and comfortable learning unfamiliar systems, tools, and business processes
• Comfortable working in a fast-moving environment with a bias toward practical, measurable results
• Collaborative, resourceful, and comfortable working independently while knowing when to involve subject-matter experts
• Bachelor's degree in Business, Operations, Analytics, Information Systems, Technology, or a related field, or equivalent practical experience
• 3+ years of experience in business operations, R&D or engineering operations, analytics, business systems, program management, AI enablement, or a related field
• Hands-on experience using generative AI tools to create or improve business workflows, reporting, analysis, or internal processes
• Experience working cross-functionally with technical teams and translating operational needs into practical solutions
• Experience working with operational data and using it to produce meaningful reporting, recommendations, or process improvements
• Experience with Atlassian products such as Jira and Confluence
• Experience with Atlassian Rovo, Rovo agents, or similar AI-enabled work-management platforms
• Experience with engineering analytics, developer productivity, or R&D reporting platforms such as Jellyfish or similar tools
• Experience developing metrics or reporting around software delivery, engineering capacity, cycle time, throughput, planning, or development workflows
• Experience with Claude and other major generative AI platforms
• Experience with AI agent builders, workflow automation platforms, or low-code/no-code automation tools
• SQL experience and familiarity working with relational or structured datasets
• Experience with BI and visualization platforms such as Power BI, Tableau, Looker, or similar tools
• Familiarity with APIs, integrations, or data pipelines sufficient to collaborate effectively with technical teams; hands-on software development experience is not required
• Experience with process improvement, operational analytics, program coordination, or project management
• Experience working in SaaS, software development, technology, or other fast-moving product environments
• Familiarity with Agile development practices and software-development lifecycle concepts
• Experience with AI governance, data governance, security, privacy, or compliance practices is a plus

Qualifications

Must Haves

• Comfortable working with structured business and operational data using SQL, spreadsheets, reporting platforms, or BI tools
• Hands-on experience using generative AI tools to solve business or operational problems
• Experience building, configuring, training, testing, and refining AI agents or AI-assisted workflows
• Strong working knowledge of Claude and the ability to build and iteratively improve Claude-based projects, agents, workflows, or other AI solutions
• Ability to evaluate AI-generated outputs for accuracy, usefulness, consistency, and appropriate use of source context
• Experience improving AI performance through prompt design, instructions, context management, source-data refinement, testing, and feedback
• Understanding of hallucination risk and practical approaches for improving the reliability of AI-generated outputs
• Experience designing AI workflows that incorporate human review or approval where appropriate
• Ability to identify practical opportunities where AI can reduce manual work, improve reporting, surface useful insights, or support better decision-making
• Comfortable experimenting with new AI capabilities and determining whether they provide meaningful business value
• Experience working closely with software engineering, product, technical, or R&D teams
• Ability to translate between technical and non-technical stakeholders and turn business needs into clear requirements, workflows, reporting, or process improvements
• Strong stakeholder-management skills, including the ability to influence, coordinate, and move work forward without direct authority
• Comfortable asking technical teams for information, clarification, or assistance while respecting competing priorities and engineering ownership
• Able to independently investigate problems, gather available context, and clearly define what assistance is needed before escalating to Engineering
• Comfortable operating as a collaborative peer within a technical environment rather than as a people manager
• Well organized and dependable, with the ability to manage multiple priorities and bring structure to ambiguous problems
• Excellent interpersonal and written communication skills, with the ability to build productive working relationships across technical and business teams
• Able to communicate technical concepts and analytical findings clearly to both technical and non-technical audiences
• High level of integrity, attention to detail, and accuracy
• Curious and comfortable learning unfamiliar systems, tools, and business processes
• Comfortable working in a fast-moving environment with a bias toward practical, measurable results
• Collaborative, resourceful, and comfortable working independently while knowing when to involve subject-matter experts
• Bachelor's degree in Business, Operations, Analytics, Information Systems, Technology, or a related field, or equivalent practical experience
• 3+ years of experience in business operations, R&D or engineering operations, analytics, business systems, program management, AI enablement, or a related field
• Hands-on experience using generative AI tools to create or improve business workflows, reporting, analysis, or internal processes
• Experience working cross-functionally with technical teams and translating operational needs into practical solutions
• Experience working with operational data and using it to produce meaningful reporting, recommendations, or process improvements

Nice to Haves

• Experience with Atlassian products such as Jira and Confluence
• Experience with Atlassian Rovo, Rovo agents, or similar AI-enabled work-management platforms
• Experience with engineering analytics, developer productivity, or R&D reporting platforms such as Jellyfish or similar tools
• Experience developing metrics or reporting around software delivery, engineering capacity, cycle time, throughput, planning, or development workflows
• Experience with Claude and other major generative AI platforms
• Experience with AI agent builders, workflow automation platforms, or low-code/no-code automation tools
• SQL experience and familiarity working with relational or structured datasets
• Experience with BI and visualization platforms such as Power BI, Tableau, Looker, or similar tools
• Familiarity with APIs, integrations, or data pipelines sufficient to collaborate effectively with technical teams; hands-on software development experience is not required
• Experience with process improvement, operational analytics, program coordination, or project management
• Experience working in SaaS, software development, technology, or other fast-moving product environments
• Familiarity with Agile development practices and software-development lifecycle concepts
• Experience with AI governance, data governance, security, privacy, or compliance practices is a plus

Benefits

• 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.
• Remote work arrangement
• Full-time employment