Trustwell

Human Resources

• Ensuring employees are paid accurately and on schedule.
• Administer employee benefits programs, including enrollments, changes, and terminations.
• Maintain compliance with applicable federal, state, and local employment laws and regulations.
• Own detail-oriented HR operations, including HRIS (Rippling) data integrity, employee files, and routine HR reporting.
• Support candidate filtering and screening for standard, high volume roles, and provide light recruiting support.

HR Generalist

Revenue Operations

• The VP, Sales Enablement & GTM Strategy is responsible for maximizing revenue productivity and driving execution excellence across Trustwell’s go-to-market organization.
• This leader serves as a strategic partner to the Chief Revenue Officer and is accountable for ensuring sales teams have the processes, training, methodologies, content, tools, and operational discipline required to consistently achieve revenue objectives.
• This role owns sales enablement, onboarding, sales readiness, forecast governance, GTM program execution, product launch readiness, performance management frameworks, and strategic revenue initiatives.
• Working closely with Revenue Operations, Marketing, Product Management, Customer Success, and Sales Leadership, this individual will translate company strategy into repeatable programs that improve effectiveness across the entire customer lifecycle.

Vice President, Revenue Enablement & GTM Strategy

Product Manager

• Understand market needs and guide product management best practices.
• Collaborate across functional teams to ensure high-quality deliverables.
• Maintain a prioritized product roadmap and overall product vision.
• Adapt project scope, schedules, and resource assignments as needed.
• Perform customer demonstrations and lead advisory boards/requirements gathering sessions.
• Identify opportunities for additional product market fit through TAM analysis and ongoing feedback.

Senior Product Manager

Data Scientist

• Define and help execute Trustwell’s applied AI strategy across product, engineering, data, and internal business operations.
• Lead the implementation of AI capabilities that are practical, measurable, secure, and aligned to business outcomes.
• Establish AI governance practices, including usage policies, risk controls, evaluation standards, approval processes, and ongoing monitoring.
• Partner with Engineering to design repeatable AI implementation patterns for LLMs, agents, retrieval-augmented generation, structured outputs, model evaluation, observability, and production operations.
• Partner with Product to identify, evaluate, and prioritize AI-enabled product opportunities that improve customer value and operational efficiency.
• Develop frameworks for assessing AI use cases, including feasibility, risk, data availability, implementation complexity, cost, and expected business impact.
• Create and maintain standards for responsible AI usage, including data handling, prompt management, model selection, explainability, auditability, and human-in-the-loop controls.
• Build and guide AI evaluation processes, including test datasets, regression testing, hallucination detection, quality scoring, accuracy measurement, and production feedback loops.
• Help establish internal AI adoption processes, including development workflows, engineering enablement, training, approved tooling, and practical usage guidelines.
• Work with Security, Legal, Compliance, and IT stakeholders to ensure AI implementations align with Trustwell’s data protection, privacy, contractual, and security obligations.
• Analyze structured and unstructured data to identify opportunities for automation, prediction, classification, summarization, enrichment, and decision support.
• Develop prototypes, proofs of concept, and production-ready analytical or AI workflows where appropriate.
• Provide technical leadership on model selection, vendor evaluation, build-versus-buy decisions, AI cost management, and long-term platform strategy.
• Collaborate with data engineering and application teams to improve data readiness, data quality, metadata, lineage, and retrieval strategies for AI-enabled systems.
• Define metrics and reporting to measure AI adoption, performance, quality, cost, risk, and business impact.
• Act as a trusted advisor and mentor to engineering, product, and business teams as they adopt AI responsibly and effectively.
• Other duties as required.

HR Generalist

Vice President, Revenue Enablement & GTM Strategy

Senior Product Manager

Lead AI & Data Scientist