Principal, Executive Operations & AI Enablement

Job Description:

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

• 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.

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.

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.

• Overall Experience: 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.

• Executive Operations Expertise: Proven experience supporting executive leadership teams and Board governance processes, including executive meetings, Board administration, agenda management, executive communications, and confidential leadership operations.

• AI Technical Literacy: 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).

• Tooling Expertise: Mastery of modern productivity and collaboration platforms including Google Workspace, Microsoft 365, Slack, Notion, Asana, ClickUp, Jira, Monday.com, or similar operational systems.

• Communication & Presence: Exceptional verbal and written communication skills with the professional presence required to comfortably influence senior executives, investors, and Board members.

• Execution Style: An unwavering ownership mindset with obsessive attention to detail, strong systems thinking, and a calm demeanor under high-stakes pressure.

We take into account an individual’s qualifications, skillset, and experience in determining final salary. This role is eligible for health insurance, life insurance, retirement benefits, participation in the company’s equity program, paid time off, including vacation and sick leave.The actual offer will be at the company’s sole discretion and determined by relevant business considerations, including the final candidate’s qualifications, years of experience, skillset, and geographic location. The expected salary range for this position is:

$125,000.00 - $165,000.00 Annual

Cityblock values diversity as a core tenet of the work we do and the populations we serve. We are an equal opportunity employer, indiscriminate of race, religion, ethnicity, national origin, citizenship, gender, gender identity, sexual orientation, age, veteran status, disability, genetic information, or any other protected characteristic.

We do not accept unsolicited resumes from outside recruiters/placement agencies. Cityblock will not pay fees associated with resumes presented through unsolicited means.