Director, Systems, Data & AI Transformation

Rockstar

About The Position

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.

Requirements

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 Haves

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

Responsibilities

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
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
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
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
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
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