Chief of Staff – AI & Automation
Location: New York, NY (Midtown)
Work Model: Primarily in-office (4+ days per week)
Bullpen is partnering with a growing New York City real estate investment sales platform to recruit a Chief of Staff – AI & Automation to help modernize and scale the business through technology, automation, and AI-driven workflows.
This is a newly created role designed to improve operational efficiency, streamline internal systems, and help leadership implement new technologies across a high-performing brokerage team.
The position will work closely with senior leadership to identify operational bottlenecks, implement AI and automation tools, and build scalable processes that allow the business to operate more efficiently as it continues to grow.
This role is ideal for someone who enjoys building systems, implementing technology, and solving complex business problems through automation and data.
The Role
The Chief of Staff – AI & Automation will sit at the intersection of operations, technology, and strategy, helping implement systems and tools that improve how the organization operates day to day.
This individual will help streamline workflows, improve data management, and ensure new systems are successfully implemented and adopted across the team.
Key Responsibilities
• Identify opportunities to automate manual workflows and operational processes
• Implement AI tools and automation solutions across the business
• Optimize CRM systems and internal technology platforms
• Manage system integrations and external technology vendors
• Improve internal data management and reporting processes
• Partner with leadership to drive operational initiatives and technology adoption
• Help implement tools that support marketing, deal tracking, and client communication
• Ensure successful rollout and training of new systems across the organization
Ideal Candidate Profile
The ideal candidate is a builder and operator who enjoys implementing technology solutions that make businesses run more efficiently.
Candidates may come from consulting, technology, proptech, or operational roles where they have led initiatives involving automation, CRM systems, or digital transformation.
Experience working in fast-paced or entrepreneurial environments is highly valued.
Qualifications
• Approximately 7–10 years of professional experience
• Experience implementing automation, AI, or digital transformation initiatives
• Familiarity with CRM systems such as Salesforce or similar platforms
• Experience managing system implementations or technical integrations
• Strong project management and problem-solving skills
• Ability to work closely with leadership and cross-functional teams
Real estate experience is helpful but not required.