Chief Technology Officer

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

• Lead the adoption of AI-augmented development workflows across the engineering organization, fundamentally increasing what the team can ship and how fast they can ship it


• Mentor engineers, product managers, designers, and business operators in new ways of working, making AI fluency a core competency across the org, not just a tooling layer for a few


• Build on the team’s existing foundation of modern tooling, agile practices, and continuous delivery to foster a culture of continuous experimentation where the team is always testing what’s newly possible and incorporating it into how they work


• Assess which elements of our platform represent durable competitive advantages and which are at risk of being commoditized or disrupted by AI


• In close partnership with the CPO, develop a technical strategy for the agentic future: how our platform should work when users discover, research, and transact through AI agents and intermediaries rather than traditional interfaces


• Identify where we are underinvested, in data, infrastructure, APIs, or capabilities, and build the roadmap to close those gaps


• Ensure our architecture is modular and adaptable, designed to evolve quickly as both the business and the underlying technology landscape change


• Unify two legacy technology platforms into a coherent, modern architecture that serves both brands and all customer segments


• Own the company’s security and infrastructure posture as AI tooling and agentic product surfaces introduce new categories of risk and complexity

Requirements

• You’ve led engineering organizations through periods of significant change: post-acquisition integration, rapid scaling, or fundamental retooling, and you have the judgment that comes from having done it, not just studied it


• You have real, hands‑on experience integrating AI into engineering workflows and are a strong enough technical architect to evaluate whether a solution, AI‑generated or otherwise, is elegant or a mess, and explain why to both technical and non‑technical audiences


• You bias toward speed. You know how to set an aggressive tempo, clear the obstacles that slow teams down, and create a culture where shipping is the default, not the exception


• You bring a sense of urgency to the work. You don't let decisions linger, you don't let projects drift, and you hold yourself and your teams to a standard that's obvious to everyone around you


• You think critically about moats and defensibility, and you connect engineering investments to business outcomes. You're comfortable in conversations about revenue, margin, and growth


• You take security and infrastructure seriously, particularly as AI introduces new categories of risk across development and product surfaces

Core Competencies

Demonstrates expertise in leading engineering organizations through significant change while integrating AI into workflows. Capable of developing technical strategies that align with business outcomes and ensuring security and infrastructure resilience in evolving technology landscapes.

Highest-signal resume keywords

• AI Integration


• Technical Architecture


• Agile Practices


• Security Posture


• Change Management

ATS Optimization Keywords

Hard Skills

• AI‑Augmented Development


• Continuous Delivery


• Modular Architecture


• Data Infrastructure


• API Development

Soft Skills

• Mentoring


• Critical Thinking


• Sense of Urgency


• Judgment


• Communication

Industry Keywords

• Competitive Advantage


• Business Outcomes


• Post‑Acquisition Integration


• Rapid Scaling


• Defensibility

Tools & Technologies

• Modern Tooling


• Legacy Technology Platforms


• Development Workflows