Principal, Executive Operations & AI Enablement

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.

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 unwaversion ownership mindset with obsessive attention to detail, strong systems thinking, and a calm demeanor under high-stakes pressure.

Qualifications

We take into account an individual’s qualifications, skillset, and experience in determining final salary.

Benefits

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

Pay

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