Startup CEO

The Role

As a CEO, you’ll bring strategic judgment, pattern recognition, and organizational insight shaped by real leadership experience. You’ll help design and review complex decision-making datasets that mirror the tradeoffs faced by senior executives — resource allocation, risk management, growth strategy, culture, and crisis response.

The work calls for clarity of thought under constraint. You’ll model how experienced leaders synthesize incomplete information, align stakeholders, and chart decisive paths through uncertainty. Your perspective will help train systems to think not just analytically, but executively — to reason in terms of impact, sequence, and consequence.

What we’re Looking for

• Executive Leadership Experience – Former CEO, President, or equivalent senior executive at a VC-backed or bootstrapped startup (required)
• Strategic Acumen – Track record of navigating complex tradeoffs and setting organizational direction across competing priorities
• Operational Depth – Understanding of how strategy translates into execution, metrics, and accountability systems
• ‍Communication Mastery – Ability to articulate decisions with clarity, empathy, and narrative coherence for diverse stakeholders

Work You Might Do

• Reviewing and refining strategic reasoning tasks to reflect how experienced executives make tradeoffs in real-world contexts
• Evaluating model-generated recommendations for clarity, realism, and operational soundness
• Contributing decision scenarios — mergers, pivots, org design, crisis management — and assessing reasoning quality
• Partnering with Surge researchers to define benchmarks for executive-level reasoning, prioritization, and judgment under pressure