Principal, Executive Operations & AI Enablement

Cityblock Health

3d•$125,000 - $165,000

About The Position

The Principal, Executive Operations & AI Enablement serves as the primary operational catalyst, executive governance lead, and AI enablement partner for the Executive Leadership Team (ELT) and Board operations. This is not a traditional administrative role; it is a high-impact, forward-looking position designed for an elite operator with exceptional executive presence, operational rigor, AI fluency, and judgment. The role combines three critical dimensions: AI-enabled executive workflow transformation and operational optimization, End-to-end governance and executive operations management for the ELT and Board of Directors, and Strategic execution support for high-priority initiatives and executive priorities. Acting as a trusted advisor and execution partner to senior leadership, this individual orchestrates executive and Board governance processes, drives operational excellence, and continuously identifies opportunities to leverage AI and automation to increase organizational efficiency and executive leverage. Success in this role requires obsessive attention to detail, exceptional organizational discipline, executive maturity, professionalism in high-stakes environments, and a relentless commitment to quality, precision, and follow-through. This individual must thrive in a fast-paced environment while seamlessly balancing strategic thinking with hands-on execution.

Requirements

Bachelor’s degree in Business, Computer Science, Engineering, or a related field preferred.
Familiarity with the operational, regulatory, and compliance considerations within value-based healthcare or high-growth technology environments is a strong plus.
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.

Nice To Haves

Familiarity with the operational, regulatory, and compliance considerations within value-based healthcare or high-growth technology environments is a strong plus.

Responsibilities

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.
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.
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.
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.
Handle highly confidential business matters with exceptional judgment, professionalism, and executive maturity.