Head of Data, AI Enablement
PushPress
full-time
Posted on:
Location Type: Remote
Location: United States
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Job Level
About the role
- We're looking for a senior leader to own our data function and AI infrastructure.
- As our first Head of Data & AI Enablement, you'll define and execute the company's data strategy from the ground up — and critically, you'll need to build organizational buy-in for that strategy and drive it to measurable outcomes. You'll own data engineering, pipeline architecture, analytics, and the data layer that feeds our AI and reporting products. Our engineering team currently owns AI infrastructure and feature development — this role ensures they have the clean, reliable, well-structured data foundation to do that effectively.
- This is a player-coach role at a growth-stage company. You'll set the vision and roadmap, but you'll also roll up your sleeves early on. A key challenge of this role is balancing the day-to-day demands — data quality issues, stakeholder requests, system syncs — with execution on a longer-term data roadmap. We need someone who won't let firefighting crowd out the strategic work.
- This role sits at the intersection of data, business strategy, and AI. You'll work closely with Dan and the leadership team to ensure our data platform powers both internal decision-making and the products our engineering team is building for customers. You'll serve as a critical bridge between the business side and the data engineering function — translating business needs into data requirements, and ensuring data work is always grounded in business context and value. On AI specifically, you'll be a key voice in shaping our approach — bringing experience with LLMs and AI agents to the table — but you won't be doing it alone. How we adopt and operationalize AI tooling is something the company is actively figuring out, and this role will help shape that alongside engineering and product leadership.
Requirements
- 8+ years of experience across data engineering, analytics, and AI, with at least 2 years in a senior leadership role
- Deep hands-on experience building and scaling data platforms in a cloud environment (we're on AWS)
- Strong IC foundation across multiple data disciplines — you've done the work yourself before leading others through it
- A systems thinker who understands business context deeply, not just technical architecture
- Strong understanding of modern data stack tooling — warehousing, ETL/ELT, orchestration, and BI
- Familiarity with the AI/ML landscape — you don't need to train models from scratch, but you should know how to evaluate tools, APIs, and approaches and make smart infrastructure decisions that support AI-powered products
- Track record of building and managing high-performing technical teams
- Proven ability to develop a data strategy, build cross-functional buy-in, and execute it to measurable results — whether hands-on or by empowering your team
- Ability to think strategically about where AI creates real value and where it doesn't
- Comfortable operating in a fast-moving, resource-constrained environment where you'll need to prioritize ruthlessly
- Excellent communicator who can translate technical concepts for non-technical stakeholders and serve as a bridge between business teams and data engineering
- Hands-on experience with LLMs and AI agents in production systems
- Background in data synchronization across multiple product surfaces and third-party integrations
Benefits
- Health insurance
- Retirement plans
- Paid time off
- Flexible work arrangements
- Professional development opportunities
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
data engineeringanalyticsAI infrastructuredata platform developmentcloud environmentAWSdata warehousingETLELTbusiness intelligence
Soft Skills
leadershipstrategic thinkingcommunicationcross-functional collaborationsystems thinkingprioritizationproblem-solvingstakeholder managementteam managementtranslating technical concepts