Note: The job is a remote job and is open to candidates in USA. Cityblock Health is a company focused on transforming healthcare delivery through innovative operational strategies. They are seeking a Principal, Executive Operations & AI Enablement to serve as the primary operational catalyst for the Executive Leadership Team, managing governance processes and driving AI-enabled operational excellence.

Responsibilities

• AI Prototyping & Workflow Transformation: Act as the internal benchmark for AI productivity. Partner 1:1 with ELT leaders to build custom AI assistants, engineer advanced prompts, automate legacy manual tasks, and introduce modern, scalable operating practices to maximize executive leverage
• Executive Governance & Board Operations: Own the end-to-end strategy and precision execution of all ELT and Board of Directors meetings. Manage complex calendars, design high-impact agendas, track action items, and maintain absolute version control over critical governance assets
• Materials & Communications QA: Serve as the final line of defense for executive outputs. Author, edit, and rigorously quality-assure Board decks, investor presentations, and strategic briefs for absolute polish, accuracy, and clarity
• Strategic Initiatives & Special Projects: Partner directly with the CEO and C-suite to independently drive high-priority cross-functional initiatives under tight deadlines, proactively surfacing operational risks and clearing execution bottlenecks
• Discretion & Trust: Handle highly confidential business matters with exceptional judgment, professionalism, and executive maturity

Skills

• Bachelor's degree in Business, Computer Science, Engineering, or a related field preferred
• 8+ years of progressive experience in Chief of Staff functions, strategic operations, management consulting, or high-level executive operations within fast-paced, high-growth environments
• Proven experience supporting executive leadership teams and Board governance processes, including executive meetings, Board administration, agenda management, executive communications, and confidential leadership operations
• Advanced hands-on proficiency with modern generative AI tools and platforms (e.g., OpenAI, Claude, custom GPTs, Microsoft Copilot, AI-enabled workflow automation tools such as Zapier or Make, and productivity-enhancing AI applications)
• Mastery of modern productivity and collaboration platforms including Google Workspace, Microsoft 365, Slack, Notion, Asana, ClickUp, Jira, Monday.com, or similar operational systems
• Exceptional verbal and written communication skills with the professional presence required to comfortably influence senior executives, investors, and Board members
• An unwavering ownership mindset with obsessive attention to detail, strong systems thinking, and a calm demeanor under high-stakes pressure
• Familiarity with the operational, regulatory, and compliance considerations within value-based healthcare or high-growth technology environments is a strong plus

Benefits

• Health insurance
• Life insurance
• Retirement benefits
• Participation in the company’s equity program
• Paid time off, including vacation and sick leave

Company Overview