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VP of Operations, Office of the Chairman

Remote

SUMMARY

The VP of Operations serves as the operational leader and strategic partner across the Chairman's portfolio of businesses, investments, and new ventures. This role owns the execution engine that translates vision into outcomes—building systems, driving accountability, and ensuring velocity across all initiatives. The VP of Operations will lead complex multi-stakeholder projects end-to-end, architect operational infrastructure, and maintain the high-urgency operating cadence required to scale multiple ventures simultaneously.

This is a hands-on leadership role responsible for driving AI-enabled initiatives from concept through deployment. The ideal candidate has run operations at a software development firm or digital agency and is ready for broader strategic scope. They bring strong technical fluency, experience implementing AI-enabled workflows, and the confidence to hold senior contributors accountable. This role also includes oversight of executive scheduling and time management to protect the Chairman's capacity for highest-impact work.

It is ideal for a builder and operator who thrives in fast-paced, entrepreneurial environments—someone who navigates ambiguity with confidence, creates structure where none exists, and brings relentless execution discipline to every initiative.

KEY RESPONSIBILITIES

Operational Leadership & Systems Building

  • Own the operational infrastructure across the Chairman's ventures—designing and implementing systems, processes, and tools that create leverage and eliminate inefficiencies.
  • Establish operating rhythms including dashboards, reporting structures, review cadences, and communication protocols across all portfolio companies.
  • Manage information flow to ensure the right inputs reach the right people at the right time.
  • Protect the Chairman's time through strategic calendar management and meeting prioritization.

Technical Execution & AI Systems Delivery

  • Lead AI-enabled initiatives from concept to live deployment, ensuring measurable business impact.
  • Design, prototype, and implement AI workflows, automation systems, and operational tools that increase speed and leverage across ventures.
  • Drive adoption of modern technical solutions that enhance operational efficiency.

Project & Venture Execution

  • Lead high-impact projects from concept through completion, coordinating across internal teams, partners, and external vendors.
  • Establish aggressive execution timelines with clear ownership, tight feedback loops, and minimal bureaucracy.
  • Escalate risks directly and immediately when deliverables or response times fall short.
  • Manage special initiatives including new business development, investment diligence, strategic partnerships, and corporate innovation.
  • Track progress, risks, deliverables, and KPIs—ensuring alignment with the Chairman's goals.

Strategic Partnership

  • Serve as a trusted thought partner to the Chairman, helping evaluate opportunities, shape priorities, and pressure-test decisions.
  • Translate high-level vision into clear plans, structures, and next steps that drive measurable progress.
  • Anticipate needs, identify blind spots, and proactively surface insights to keep initiatives on track.

Stakeholder and Relationship Management

  • Represent the Chairman in select meetings, communications, and negotiations—ensuring continuity and alignment.
  • Prepare briefs, talking points, memos, and follow-ups for internal and external engagements.
  • Maintain and strengthen relationships with senior executives, partners, investors, board members, and strategic collaborators.

Communications and Analysis

  • Produce executive-level summaries, recommendations, presentations, and research that support strategic decisions.
  • Synthesize information across businesses, markets, and teams into concise, actionable insights.
  • Drive follow-through to ensure decisions become outcomes.

QUALIFICATIONS

  • 7-12 years of operational leadership experience, ideally as a COO, VP of Operations, Development Manager, or senior technical leader at a software development firm, digital agency, or technology company.
  • Demonstrated experience building and implementing AI workflows, automation systems, or AI-enabled operational tools—not just experimentation or prompt usage.
  • Track record of building operational systems and processes that scale.
  • Experience managing cross-functional teams and holding senior contributors accountable.
  • Strong technical fluency—comfortable working alongside engineers and evaluating technical approaches.
  • Exceptional written and verbal communication skills with executive presence.
  • Highly organized with the ability to manage complex workflows across many concurrent initiatives.
  • Strong analytical and problem-solving skills; able to synthesize complexity quickly.
  • High integrity, emotional intelligence, and discretion.

PREFERRED

  • Experience as a Chief of Staff or in close operational partnership with a founder, CEO, or principal.
  • Background in a fast-paced, entrepreneurial environment with shifting priorities.
  • Bachelor's degree in Business, Information Science, Computer Science, or related field; advanced degree a plus.
  • Advanced proficiency in productivity platforms, project management tools, and modern collaboration software.

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