Jobgether
AI Chief of Staff
TLDR
High-impact, executive-facing role driving enterprise AI transformation for mid-market organizations, aligning strategy with measurable business outcomes.
Accountabilities:
- Lead executive-level AI transformation engagements, acting as a trusted advisor to C-suite stakeholders across priority client accounts
- Facilitate monthly AI steering committee sessions, aligning executives on strategy, priorities, KPIs, and transformation roadmaps
- Translate business strategy into actionable AI transformation roadmaps tied to financial and operational outcomes
- Drive execution between executive sessions by coordinating internal delivery teams and client stakeholders to maintain momentum
- Identify and remove organizational and operational blockers that slow down AI adoption and workflow transformation
- Produce board-ready reporting and ROI analyses that clearly connect AI initiatives to measurable business value
- Surface new growth opportunities within client relationships and support expansion scoping through consultative engagement
- Act as the primary liaison between executive leadership and technical delivery teams, ensuring alignment and clarity across all workstreams
- Capture insights from client engagements to inform product development, playbooks, and AI adoption frameworks
- Help shape and refine the AI Chief of Staff operating model as the function scales
- 8–10+ years of experience in management consulting, professional services, or strategic advisory roles working with senior executives
- Proven ability to facilitate C-suite discussions and drive alignment across complex, multi-stakeholder organizations
- Strong understanding of business models, P&L structures, KPIs, and enterprise operating rhythms across industries
- Experience delivering executive-level deliverables, including strategic roadmaps and board-ready presentations
- Demonstrated ability to drive complex, cross-functional initiatives from strategy through execution
- Strong commercial acumen with experience identifying and supporting expansion opportunities within client accounts
- Familiarity with AI tools and a strong interest in applying AI to business transformation and operational redesign
- Ability to quickly understand new industries and translate business context into structured execution plans
- Exceptional communication and stakeholder management skills, with presence in executive environments
- Self-directed, highly organized, and comfortable operating in ambiguous, fast-moving transformation programs
- Competitive compensation with potential for performance-based incentives
- Opportunity to work directly with executive leadership on high-impact AI transformation initiatives
- Flexible remote-first work environment within the United States
- Exposure to cutting-edge AI adoption and enterprise transformation programs
- Direct involvement in shaping a new, high-growth function and operating model
- Support from specialized delivery teams (product, engineering, adoption, and project management)
- Opportunity to influence product direction, client strategy, and organizational playbooks
- High autonomy role with significant ownership over client success and strategic outcomes.
Requirements:
Benefits:
How Jobgether works:
We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.
We appreciate your interest and wish you the best!
Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.
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Benefits
Remote-Friendly
Flexible remote-first work environment within the United States
Jobgether runs the largest remote job platform, effectively linking job seekers with over 200,000 flexible and remote opportunities that match their unique skills and preferences. Our focus is on enhancing the hiring process, ensuring efficiency while prioritizing the candidate experience, particularly in the growing health and wellness sector.
- Founded
- Founded 2020
- Employees
- 11-50 employees
- Industry
- Professional Services
Chief of Staff