Chief of Staff - Engineering & AI Automation

If you haven't built and scaled a 0-1 product to at least 7-figure (USD) ARR and/or been part of a YC (or equivalent startup) founding engineer team we kindly ask that you don't apply for this role. Our client is looking for a hands-on engineering leader who has deep expertise in AI automation, keeps up with the latest AI research for fun, and has previously led technical early-stage startups in a YC batch (or an equivalent high-growth environment).

About Us

Our client is an innovative startup revolutionizing how businesses operate through AI and automation. With a focus on engineering excellence and scalable automation solutions, we are building the future of intelligent workflows. To drive this mission, we are seeking a highly skilled Chief of Staff - Engineering & AI Automation. This role is for someone deeply embedded in the startup and AI ecosystem, with extensive experience in engineering leadership and AI-powered automation systems.

Role Overview

As the Chief of Staff - Engineering & AI Automation, you will report directly to the CEO and play a critical role in driving the company's engineering and automation initiatives. You will lead the development of AI-powered automation systems, oversee engineering excellence, and ensure seamless integration with existing business processes. This role requires a unique combination of engineering leadership, AI expertise, and strategic thinking to develop scalable automation solutions that align with company goals. You will bridge technical teams and executive leadership, driving innovation in AI automation while maintaining engineering best practices. This is a fully remote position.

Key Responsibilities

1. Engineering Leadership & AI Automation

- Lead the architecture and development of advanced automation systems integrating LLMs and other AI technologies

- Oversee the engineering team's development of full-stack applications that leverage AI models for automation

- Design and implement scalable automation frameworks that can handle complex business workflows

- Drive engineering excellence and best practices across all automation initiatives

2. Strategic Technical Leadership

- Partner with engineering teams to identify automation opportunities and design AI-driven solutions

- Bridge technical execution and strategic decision-making to ensure engineering initiatives align with company objectives

- Develop metrics and KPIs to measure the effectiveness of automation systems and engineering processes

- Guide technical architecture decisions and technology stack choices

3. AI Research & Engineering Innovation

- Lead research initiatives in automation technologies, including LLMs, multi-agent systems, and emerging frameworks

- Architect and deploy scalable automation infrastructure suitable for high-growth environments

- Drive continuous improvement in automation systems through performance optimization and enhanced capabilities

- Establish engineering standards for AI model deployment and maintenance

4. Technical Vision & Industry Leadership

- Shape the company's technical vision for automation and engineering excellence

- Serve as an advisor to leadership on engineering trends, automation technologies, and technical strategy

- Contribute to the company's thought leadership through technical publications and speaking engagements

- Build relationships with key technology partners and industry leaders

5. Engineering Team Development

- Mentor engineering teams on automation best practices, architecture patterns, and optimization techniques

- Foster a culture of engineering excellence and innovative problem-solving

- Implement and oversee engineering processes that enable rapid, reliable automation development

- Guide the adoption of cutting-edge development tools and practices

Who You Are

- You have a proven track record of leading engineering teams and implementing large-scale automation systems

- You have significant experience in high-growth startup environments and understand how to scale engineering operations

- You are a technical visionary who can translate business needs into automated solutions

- You excel at cross-functional leadership, bridging engineering, product, and business teams

- You are deeply passionate about engineering excellence and advancing the state of AI automation

Qualifications

a. Technical Leadership

- 8+ years of experience in engineering leadership or technical management

- Strong background in automation engineering and AI system architecture

- Expertise in modern development practices, CI/CD, and engineering operations

- Deep understanding of LLMs, AI models, and automation frameworks

- Proven experience scaling engineering teams and automation systems

- Strong foundation in software architecture and system design

b. Automation & AI Expertise

- Extensive experience with automation platforms and AI technologies

- Strong proficiency in Python, JavaScript, and modern development frameworks

- Deep knowledge of LLMs, vector databases, and AI orchestration tools

- Experience with advanced automation techniques including RAG and fine-tuning

- Proven track record of implementing successful automation solutions

c. Leadership & Communication

- Outstanding leadership and team management abilities

- Excellent communication skills with both technical and non-technical stakeholders

- Strong strategic thinking and problem-solving capabilities

- Proven ability to drive engineering excellence and innovation

What We Offer

- Leadership role in shaping the future of AI automation and engineering excellence

- Opportunity to build and scale cutting-edge automation systems

- High-impact position driving technical innovation in a fast-growing startup

- Fully remote work with flexible arrangements

- Competitive compensation package

How to Apply

Please submit your resume, portfolio, and a brief cover letter detailing:

1. Your experience leading engineering teams and implementing automation systems

2. Examples of large-scale automation projects you've successfully delivered

3. Your vision for the future of AI automation and engineering excellence

If you are passionate about engineering leadership and driving innovation in AI automation within a high-growth startup, we'd love to hear from you!