Operations Manager, Customer Success & AI Enablement

Whip Around

8d•$105,000 - $125,000•Remote

About The Position

Whip Around is seeking an Operations Manager to support AI tools and Customer Success systems. This role will work closely with the Director of Operations to support AI development and accuracy, maintain integrations and Customer Success tools, and strengthen AI models. The position also supports the systems that drive AI models and focuses on AI enablement for Customer Success, identifying opportunities for AI and automation, turning experiments into repeatable use cases, and embedding tools into workflows. The ideal candidate has hands-on experience improving Customer Success outcomes through AI use cases and can demonstrate delivered value.

Requirements

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.
Evaluate emerging AI models, tools, and techniques, and recommending pragmatic adoption.
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.
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.
Experience implementing, configuring, or significantly expanding Customer Success applications and workflows.
Ability to translate operational requirements into practical, scalable system solutions.
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.
Able to work independently from high-level technical or process direction.
Comfortable balancing project-based system development with day-to-day Salesforce and Customer Success platform administration and support.
Well organized and dependable, with the ability to manage multiple priorities, work independently, and bring structure to ambiguity.
Strong analytical and problem-solving skills.
Excellent interpersonal and written communication skills.
Able to communicate complex technical concepts clearly and document system design, configuration, decisions, and dependencies.
Comfortable working from defined architectural direction while independently determining and executing the detailed steps required to deliver a solution.
Collaborative approach to systems development.
Ability to design solutions with maintainability, extensibility, and future change in mind.
Strong attention to detail, accuracy, and data integrity.
Experience with process improvement and project coordination.
Solid working understanding of data and metadata.
Comfortable working in a fast-moving, growing environment where requirements evolve.
Receptive to feedback and willing to challenge or refine an approach constructively.
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.
Experience owning or contributing substantially to system implementations, integrations, migrations, or significant platform changes.
Hands-on experience delivering automation or AI solutions for real-world business workflows.

Nice To Haves

Experience with enterprise security, governance, privacy, compliance, and access-control practices.
Familiarity with Git, source control, deployment practices, and software engineering principles.
Experience with API-based integrations, including REST/SOAP concepts, authentication, data mapping, error handling, and troubleshooting.
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.
Strong proficiency with Microsoft Excel, including advanced formulas and data manipulation.
Experience with BI and visualization tools such as Tableau or Power BI.
Prior experience implementing, configuring, migrating, or redesigning Customer Success platforms or related business applications.
Experience supporting system integrations, platform migrations, or application transitions.
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.
Experience evaluating new tools or platform capabilities with consideration for integration requirements, long-term maintainability, scalability, and total operational impact.
Experience designing, building, or deploying generative AI or agentic solutions.

Responsibilities

Manage day-to-day operations within Customer Success tools, supporting workflows, resources, and projects.
Track and report on operational KPIs against targets, flagging performance gaps and implementing corrective actions.
Manage operational budgets and tools, monitoring spend and ensuring value from systems and vendors.
Support the rollout and adoption of AI and automation tools through guides, training, and hands-on assistance.
Identify and prioritize practical AI use cases focused on reducing manual effort, improving consistency, and saving time or cost.
Develop promising AI experiments into reliable, repeatable use cases, including gathering requirements, validating outputs, supporting rollout, and ongoing maintenance.
Deliver early "quick wins" and establish routines for monitoring and improving solutions.
Ensure live AI tools are fed with accurate, current information for reliability and trust.
Map and improve core operational processes, identifying bottlenecks for automation or AI.
Maintain and improve core systems (e.g., Salesforce, Hubspot, Jira, Mixmax), flagging integration gaps or usability issues.
Document processes, tools, and standard operating procedures.
Manage and monitor new system integrations for the Customer Success team.
Gather data needs from teams and translate them into reports, dashboards, and insights.
Run regular audits of key business data to ensure accuracy and resolve variances.
Prepare monthly and quarterly analytics for leadership, explaining findings to technical and non-technical audiences.
Collaborate with the Director of Operations and partner with Sales, Customer Success, Finance, and Product Operations.
Bring structure, timelines, and follow-through to operational projects.
Provide documentation, support, and training for internal users.
Follow and help maintain responsible-use, data privacy, and quality controls for AI and automation.
Support compliance with data privacy regulations and partner with the Tech team on security.
Flag operational risks early and perform other duties as assigned.