Chief of IT and AI
About The Position
We're looking for a sharp, forward-thinking Chief of IT & AI who brings energy, curiosity, and a passion for AI to one of the most unique work environments around. You'll be the driving force behind our technology strategy — helping our team work smarter, our operations run smoother, and our members enjoy an experience that feels seamless, modern, and exceptional. As our Chief of IT & AI, you'll own our technology ecosystem from end to end — infrastructure, applications, data, and the AI-powered tools that make our operations hum. You'll work side-by-side with department heads, frontline staff, and senior leadership to identify opportunities, build solutions, and deliver measurable results. You're as comfortable presenting to the board as you are rolling up your sleeves with the team.
Requirements
- 3+ years of hands-on experience taking AI and automation tools from concept to execution — real implementations, real results
- Proven ability to translate technical complexity into plain language for non-technical stakeholders; you build consensus, not confusion
- Experience deploying automation that reduces manual work, eliminates bottlenecks, and empowers teams with better data
- Comfort moving quickly across industries or contexts — you learn the workflows, pain points, and KPIs that matter and get up to speed fast
- Strong proficiency with modern tools such as Python, SQL, Power BI/Tableau, Power Automate, UiPath, Azure ML, or AWS SageMaker
- Excellent communication skills — whether you're presenting to senior leadership, facilitating a staff training, or writing up a proposal, you're clear, confident, and engaging
- A collaborative spirit and low ego — you succeed when the team succeeds
- Passion for continuous learning and a genuine excitement about what AI can do next
Nice To Haves
- Experience in hospitality, golf, country club, or member services environments
- Familiarity with golf management platforms or club operations software
- A single-digit handicap (okay, this one's optional — but we won't complain)
Responsibilities
- Lead the adoption and implementation of AI and automation tools that turn operational challenges into competitive advantages — from process optimization and quality control to reporting and day-to-day efficiency
- Bridge the gap between our technical infrastructure and business goals — communicating complex solutions in plain language and building buy-in across every level of the organization
- Deploy smart automations that eliminate manual bottlenecks, giving our team better data to make faster, smarter decisions
- Identify and leverage technology to elevate the member experience — think digital check-ins, personalized communications, tee time optimization, and beyond
- Manage and support core IT systems including networks, hardware, cloud platforms, and business applications
- Be the go-to resource for staff at all levels — delivering training, support, and guidance with patience and clarity
- Stay ahead of emerging tech trends, especially in AI/ML, and bring the best ideas back to the team
- Own IT vendor relationships, contracts, and budgets
Benefits
- Comprehensive health, dental, and vision insurance
- Retirement plan with employer contribution
- Generous PTO and paid holidays
- Professional development budget — we invest in your growth
- Employee perks including golf privileges
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
