Executive Director of AI Research, Trilogy (Remote) - $200,000/year USD

at  Crossover

Are you tired of your technical discoveries getting lost in internal wikis and having to simplify your findings for broader audiences? We are seeking someone passionate about exploring the cutting edge of AI and eager to become a definitive expert in this field.
This role allows you to do what you love: writing code to test new AI tools, creating automated benchmarks, and identifying edge cases, all while having the freedom to share your insights publicly. You’ll play a pivotal role in shaping how over 150 enterprise software companies implement AI, influencing the frontier of AI capabilities and discovering breakthrough approaches.
With an AI-first approach, this role empowers a one-person team to achieve more than what traditional teams of 10+ people could deliver in the same time. You’ll research and develop innovative solutions and architectures that redefine what’s possible in AI. Instead of feeling constrained by management overhead or corporate politics, you’ll focus entirely on exploring AI’s potential.
Your work will involve coding prototypes, running experiments, and producing detailed technical content for engineering teams to implement. Rather than gathering dust in presentations, your research will directly impact how companies build and deploy AI systems.
If you’re excited about uncovering new AI capabilities, challenging vendor claims, and finding innovative solutions, and you enjoy sharing these discoveries, this position is perfect for you. Within a year, you will be recognized as a leading voice on AI’s practical limits and possibilities.
Ready to push the boundaries of AI? Apply today.

CANDIDATE REQUIREMENTS

• Deep understanding of LLM architectures, capabilities, and limitations
• Hands-on experience with prompt engineering and model evaluation
• Strong coding abilities across multiple languages
• Experience building automated testing and benchmarking frameworks
• Proven ability to rapidly prototype and test new technologies
• Track record of clear technical writing and public discourse
• Strong analytical skills with the ability to identify patterns and draw actionable conclusions
• Comfortable forming and defending bold technical positions
• Excited about daily content creation and public sharing

THIS POSITION IS ALSO KNOWN AS:

• VP of AI Research and Development
• VP of Artificial Intelligence
• VP of AI Research
• VP of Artificial Intelligence Innovation

WHAT YOU WILL BE DOING

• Writing code to test and benchmark AI tools and capabilities
• Creating prototype implementations to understand technical limitations
• Developing automated testing frameworks for systematic tool evaluation
• Building proof-of-concept integrations to verify vendor claims
• Producing daily technical research documents based on your hands-on testing
• Writing daily blog posts and Twitter updates sharing your discoveries
• Developing controversial but well-supported viewpoints on AI implementation
• Building a following of 50K+ technical professionals who rely on your insights

WHAT YOU WILL NOT BE DOING

• Managing teams or roadmaps
• Creating high-level strategy documents
• Building production systems
• Attending endless meetings
• Writing reports that never get implemented

KEY RESPONSIBILITIES

Produce authoritative technical research and implementation guidance that enables portfolio companies to effectively harness AI capabilities and maintain competitive advantage in AI adoption.