Chief of Staff & AI Transformation Leader

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Position Summary

The Chief of Staff & AI Transformation Leader is a newly created executive role that sits at the intersection of strategic execution and enterprise AI adoption. Reporting directly to the CEO, this individual will act as a force multiplier for the executive team driving alignment on top company priorities, running the operating cadence of the business, and leading Avionte's AI transformation agenda across both internal operations and the company's product and customer experience.
This is a hybrid strategy-and-execution role for someone equally comfortable advising the CEO on organizational priorities and rolling up their sleeves to stand up AI tools, workflows, and governance across the company. The ideal candidate combines chief-of-staff rigor structured thinking, cross-functional influence, and flawless execution with genuine depth in applied AI and a track record of driving adoption at scale.

Key Responsibilities

Chief of Staff & Executive Operations
  • Serve as a trusted strategic advisor and thought partner to the CEO, providing counsel on priorities, decisions, and organizational design.
  • Own the operating rhythm of the executive team: leadership meetings, quarterly planning, OKRs/goal-setting, and board meeting preparation with the CFO
  • Drive cross-functional alignment on top company priorities, ensuring initiatives move from strategy to execution with clear ownership and accountability.
  • Lead special projects and high-priority initiatives end-to-end, from problem framing through execution and results reporting.
  • Synthesize input from across the organization into clear recommendations and decision-ready materials for the executive team and board.
AI Transformation — Internal Adoption & Productivity
  • Develop and lead Avionte's enterprise AI strategy and roadmap for internal operations, in partnership with IT, People, and functional leaders.
  • Drive adoption of AI tools and workflows across departments (Sales, Customer Success, Engineering, Marketing, People, Finance) to improve productivity and decision-making.
  • Identify, prioritize, and stand-up automation and AI use cases with measurable ROI; track and report on productivity and efficiency gains.
  • Establish responsible AI governance: usage policies, data/security guardrails, and vendor evaluation criteria, in partnership with IT/Security and Legal.
  • Build AI literacy across the organization through training, enablement resources, and a network of AI champions in each function.
AI Transformation — Product & Customer Experience
  • Partner with Product and Engineering leadership to help shape how AI is embedded into Avionte's staffing and recruiting software roadmap.
  • Support Marketing and Sales with AI-related value proposition, messaging, and enablement for customer-facing conversations.
  • Monitor competitive and industry trends in AI for staffing, recruiting, and broader HR technology, translating them into actionable recommendations with the CPO
Change Leadership & Communication
  • Build a coalition of sponsors and champions across the business to drive sustained AI adoption and cultural change.
  • Communicate the AI transformation vision, progress, and impact clearly to employees, executives, and the board.
  • Anticipate and manage change resistance with empathy, clear communication, and pragmatic sequencing of initiatives.

Qualifications

Required
  • 8–10+ years of experience in strategy, business operations, management consulting, or a chief of staff / chief operating role.
  • Demonstrated experience leading AI, automation, or digital transformation initiatives at an organizational level.
  • Strong working knowledge of AI/ML concepts, generative AI and large language models, and their practical enterprise applications.
  • Proven ability to operate as a trusted advisor to senior executives, with excellent judgment and discretion.
  • Exceptional program and project management skills, with a track record of driving complex, cross-functional initiatives to completion.
  • Outstanding written and verbal communication skills; able to distill complexity into clear, actionable recommendations.
  • Bachelor's degree required.
Preferred
  • MBA or other advanced degree.
  • Experience in SaaS, HR technology, or the staffing and recruiting industry.
  • Prior experience partnering directly with a CEO or founder in a Chief of Staff, VP Strategy, or similar capacity.
  • Hands-on experience evaluating or deploying enterprise AI tooling (e.g., Copilot, Claude, custom LLM applications, workflow automation platforms).

Success Metrics

  • Adoption rate and utilization of AI tools across departments.
  • Measurable productivity and efficiency gains (time saved, cost avoided/reduced) tied to AI initiatives.
  • Number and impact of AI-enabled product features shipped in partnership with Product/Engineering.
  • Employee AI literacy and training completion rates.
  • Executive team and board satisfaction with strategic execution and operating cadence.
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