Chief of Staff: Strategy, Operations & AI-Driven Execution

Jobtailor; San Diego (CA); Hybrid; USD 130,000 - 185,000; Full time

Job summary

Jobtailor in San Diego, CA, seeks an experienced Chief of Staff / Strategic Advisor to work with the CEO, translating priorities into action and aligning the organization across functions.

You will own the OKR process, prepare board materials, manage executive meetings and offsites, and pilot AI tools to streamline operations, while championing effective communications and cross‑functional collaboration.

Qualifications

• 5+ years in executive operations, management consulting, or related roles.
• Experience supporting C-level executives or founders in Chief of Staff, Business Manager, or Strategic Advisor roles.
• Strong strategic thinking and problem-solving abilities.
• Exceptional written and verbal communication skills.
• Highly organized with attention to detail.
• Ability to manage multiple initiatives under tight deadlines.
• High EQ and interpersonal intelligence.
• Ability to influence, mediate, and build trust across levels.
• Discretion and professionalism handling confidential information.
• AI fluency and ability to identify/adopt AI tools.
• Legal eligibility to work in Canada or the USA.
• Ability to work on a hybrid model, typically three days per week at a hub location.

Responsibilities

• Act as trusted advisor to the CEO.
• Drive strategic alignment, operational execution, and organizational effectiveness.
• Translate executive priorities into action.
• Optimize internal processes and facilitate cross-functional collaboration.
• Work closely with the CEO and executive team as a thought partner, problem-solver, and operational lead.
• Own executive meetings, business reviews, board meetings, and offsites, including agendas, pre-reads, decisions, and follow-through.
• Own the OKR process end-to-end and provide business-status visibility to the CEO and leadership team.
• Prepare board materials, executive presentations, and briefings for critical meetings.
• Lead cross-functional initiatives and hand them off cleanly.
• Identify, pilot, and roll out AI tools to streamline internal processes.
• Shape communications for town halls, company updates, and speaking engagements.
• Stand in for the CEO where appropriate.
• Help the CEO prioritize and pressure-test decisions.
• Champion AI adoption across the executive team by identifying use cases, vetting tools, running trainings, and coaching executives.

Skills

Executive Operations

Strategic Thinking

Project Management

AI Fluency

Communication Skills

Organizational Skills

Interpersonal Intelligence

Influencing Skills

Discretion

Cross-Functional Collaboration

Tools

AI Tools

Presentation Software

Job description

Jobtailor in San Diego, CA, seeks an experienced Chief of Staff / Strategic Advisor to work with the CEO, translating priorities into action and aligning the organization across functions.

You will own the OKR process, prepare board materials, manage executive meetings and offsites, and pilot AI tools to streamline operations, while championing effective communications and cross‑functional collaboration.