Chief of Staff (Remote AI Evaluation Contract)

Join Jobtacular as a remote Chief of Staff (Remote AI Evaluation Contract) ($150,000 - $250,000/year). We partner with leading AI research laboratories across major English-speaking markets to evaluate complex responses, design realistic domain scenarios, and calibrate next-generation foundation models using deep professional expertise in Strategic Thinking & Business Acumen, Operational Excellence & Execution, Executive Communication & Stakeholder Management, AI Fluency & Automation Mindset.

What You Will Do

• Drive cross-functional initiatives, align stakeholders, track milestones, and ensure critical deliverables are completed.
• Identify inefficiencies, improve processes, and build scalable systems that increase organizational effectiveness.
• Develop reporting frameworks, monitor KPIs, and surface actionable insights to support business decisions.
• Prepare presentations, draft internal communications, and ensure alignment on executive priorities.
• Research business challenges, evaluate opportunities, and develop data-driven recommendations.
• Own high-impact, ambiguous initiatives that fall outside traditional departmental responsibilities.
• Leverage AI tools and automation to streamline workflows, improve productivity, and accelerate execution.

Who We Are Looking For

• Experience supporting a CRO, CEO, or other C-level executive.
• Background in AI companies, high-growth startups, or B2B SaaS.
• Working knowledge of go-to-market strategies, revenue operations, sales pipelines, and CRM systems.
• Experience building KPI dashboards, executive reporting systems, or operational workflows from scratch.
• Background in management consulting, strategic finance, or a founder's office.
• Practical background using LLMs, AI agents, and workflow automation platforms.
• Compensation & Benefits Notice

Compensation & Remote Structure

• Compensation Rate: $150,000 - $250,000/year (contract specialist remuneration)
• Work Arrangement: 100% Remote / Work From Home
• Eligible Remote Countries: United States, United Kingdom, Canada, Australia, New Zealand, Ireland, and South Africa
• Core Competencies: Strategic Thinking & Business Acumen, Operational Excellence & Execution, Executive Communication & Stakeholder Management, AI Fluency & Automation Mindset
• Hiring Agency: Jobtacular

Direct Application Process: Click the Apply button on this page to proceed directly to our partner application portal and submit your profile for immediate consideration.