Director, Systems, Data & AI Transformation

Rockstar is recruiting for a dynamic SaaS company seeking to scale intelligently through systems, data, and AI. Our client is a fast-growing organization that values strategic architecture and hands-on execution to enable reliable decision-making and drive transformative growth.

We are seeking a hands-on, strategic leader to own and evolve the business systems, data architecture, and AI transformation roadmap.

This role operates at the intersection of systems, data, and execution—responsible for building the foundation that enables scalable growth, reliable decision-making, and AI-driven capabilities across the organization. The candidate will lead cross-functional technical initiatives across Finance, GTM, Product, and Operations, combining hands-on execution with clear stakeholder alignment and delivery discipline.

This is a player-coach role that combines program leadership, systems architecture, and hands-on execution in a fast-growing SaaS environment.

Key Responsibilities

AI Transformation Leadership

• Own and drive the AI transformation roadmap, advancing maturity from early-stage (Level 0–1) to scalable adoption (target: Level 3)
• Identify and prioritize high-impact AI use cases across Finance, GTM, and Product in partnership with functional leaders
• Lead execution of AI initiatives, including workflow automation and agentic AI capabilities
• Ensure foundational systems and data structures are designed to support scalable AI adoption

Enterprise Systems & Data Architecture

• Own the architecture and evolution of the business systems ecosystem across all functions
• Define how core systems (e.g., HubSpot, NetSuite, Snowflake, and others) integrate, interact, and scale
• Establish and maintain a unified data model and clear system-of-record definitions across the organization
• Evaluate and guide selection of tools, platforms, and data infrastructure (e.g., warehouse, ETL, BI)
• Design data flows and system interoperability to enable reporting, automation, and AI use cases
• Act as the primary steward of business data integrity, consistency, and accessibility

Business Systems Ownership (Hands-On)

• Own administration and optimization of key business systems, with a willingness to be hands-on where needed (e.g., configuration, field creation, workflow updates)
• Partner with RevOps, Finance, and other stakeholders to ensure systems support evolving business needs
• Provide architectural guidance for CRM (HubSpot) and ERP (NetSuite), while collaborating with functional owners on day-to-day usage
• Ensure systems are scalable, well-structured, and aligned with downstream reporting and analytics requirements

Data, BI & Decision Enablement

• Partner with Finance and RevOps to implement and scale business intelligence capabilities
• Support the development of data models, reporting layers, and dashboards that enable real-time decision-making
• Help define and standardize key metrics, KPIs, and reporting frameworks across the organization
• Improve data quality and reliability across systems and reporting environments

Cross-Functional Program Leadership

• Serve as the program manager for high-impact, cross-functional initiatives across Finance, GTM, Product, and Operations
• Establish structure, accountability, and execution rigor across strategic projects
• Align stakeholders, manage dependencies, and ensure initiatives are delivered on time and with clear outcomes
• Act as a connective layer across teams to drive progress and reduce organizational friction

Business Process & Systems Alignment

• Identify gaps where systems, data, and processes are disconnected
• Design and implement scalable workflows that improve efficiency and data integrity
• Partner with RevOps and other functional leaders to ensure process changes are supported by strong systems design

What Success Looks Like (12 Months)

• AI maturity advances to Level 4 with clearly defined and operational use cases
• A cohesive systems architecture is established, with clear integration patterns across HubSpot, NetSuite, and data platforms
• A reliable data foundation is in place, with a defined source of truth and improved data consistency across systems
• Business intelligence capabilities are implemented and actively used by leadership
• Cross-functional initiatives are executed with greater speed, clarity, and accountability
• Systems and data are structured to support automation and future AI expansion

Qualifications

• 7–12+ years of experience in business systems, systems architecture, integration engineering, enterprise applications, automation, data platforms, or technical business systems roles in a B2B SaaS environment
• Proven ability to lead cross-functional initiatives in a SaaS or technology-driven environment
• Strong understanding of systems architecture, data modeling, and data flows across business applications
• Hands-on experience working with business systems (e.g., CRM, ERP) and data platforms (e.g., Snowflake or equivalent)
• Must have personally designed, built, or implemented systems integrations, automation workflows, data pipelines, or AI-enabled workflows—not only managed teams or vendors delivering them
• Experience implementing or scaling BI tools and reporting frameworks
• Familiarity with AI, automation, or workflow tooling, with a strong interest in driving AI adoption
• Ability to operate as both a strategic architect and hands-on executor in a lean environment
• Excellent communication skills, with the ability to work across technical and non-technical stakeholders

Nice to Have

• PMP or equivalent program management experience
• Background as a developer, systems architect, or technical operator
• Experience designing or scaling data infrastructure in a SaaS environment
• Exposure to AI-enabled workflows or agentic AI systems
• Located in US East or Central time zone

Why This Role Matters
This role is central to how the company scales. The candidate will define how the systems, data, and AI capabilities come together—enabling smarter decisions, more efficient execution, and a more connected, intelligent organization.