CTO — AI-Driven Engineering & Platform Strategy

Jobtailor; New York (NY); On-site; USD 230,000 - 360,000; Full time

Job summary

Jobtailor is seeking a senior engineering leader to drive AI-augmented development workflows across the organization, increasing speed and quality. You will mentor teams across engineering, product, design, and business operations to make AI fluency a core competency.

You will build on modern tooling, agile practices, and continuous delivery to foster a culture of experimentation while aligning architectural strategy with business goals and risk management.

Qualifications

• Led engineering organizations through periods of significant change (post-acquisition integration, rapid scaling, or fundamental retooling).
• Hands-on experience integrating AI into engineering workflows; able to evaluate whether a solution is elegant or a mess and explain why.
• Bias toward speed; set an aggressive tempo and remove obstacles to speed up shipping.
• Sense of urgency; decisions and projects should not linger or drift.
• Connect engineering investments to business outcomes like revenue, margin, and growth.
• Approach security and infrastructure seriously as AI introduces new risk categories.

Responsibilities

• Lead the adoption of AI-augmented development workflows across the engineering organization.
• Mentor engineers, PMs, designers, and operators to make AI fluency a core competency.
• Build on the team’s tooling, agile practices, and CD to foster continuous experimentation and rapid validation.
• Assess which platform elements are durable competitive advantages vs. risk of AI commoditization.
• Develop a technical strategy with the CPO for AI agents in discovery, research, and transactions.
• Identify underinvested data, infra, APIs, or capabilities and roadmap the fixes.
• Ensure architecture remains modular and adaptable as tech and business evolve.
• Unify two legacy platforms into a coherent modern architecture for all brands and customers.
• Own security and infrastructure posture as new AI tools introduce risk.

Skills

AI Integration

Technical Architecture

Agile Practices

Change Management

Mentoring

Communication

Tools

Modern Tooling

Legacy Platforms

Development Workflows

Job description

Jobtailor is seeking a senior engineering leader to drive AI-augmented development workflows across the organization, increasing speed and quality. You will mentor teams across engineering, product, design, and business operations to make AI fluency a core competency.

You will build on modern tooling, agile practices, and continuous delivery to foster a culture of experimentation while aligning architectural strategy with business goals and risk management.