Director Of Engineering – Ai - first Leadership - Remote Eligible

Director Of Engineering (AI-First)

Lead and scale a high-performing AI-first engineering organization that is pioneering the orchestration of intelligent agents and sub-agents. Drive innovation at the cutting edge of AI-enabled software development in a fast-paced, results-oriented environment, consistently delivering transformative, high-quality solutions that set new industry standards.

As Rev.io's Director of Engineering (AI-First), you will lead the evolution of our engineering organization into a model for AI-native software development. Reporting directly to the CTO, you will guide senior engineers and technical leaders in building, deploying, and orchestrating autonomous AI agents and sub-agents across our SaaS billing platform and beyond. This is a bar-raising role where success means more than incremental improvements—it means delivering breakthrough outcomes at the frontier of technology. You will shape the organizational structure, processes, and culture to support AI-first development at scale, ensuring speed, quality, and measurable business impact. You will lead a team of senior-level engineers within a growing company, balancing agent-driven greenfield innovation with modernizing core systems. Your mandate: to empower your team to solve the most complex challenges while instilling the discipline, tools, and metrics needed to achieve consistently exceptional results.

Technology & Innovation Stack

• Core AI/Agentic Development: AI agent frameworks, orchestration platforms, LLM integration, prompt engineering, sub-agent coordination.
• Languages: Python, C#, React, Lua, ASP.NET Core, SQL.
• Databases: SQL Server, Redis, PostgreSQL, MySQL.
• DevOps & Automation: GitHub/Bitbucket, CI/CD (TeamCity, Octopus Deploy), automated testing, AI-in-the-loop quality controls.
• Collaboration & Tracking: JIRA, Confluence, AI-driven project analytics.

Key Responsibilities

Strategic Leadership

• Collaborate with the CTO and senior leadership to define and execute an AI-first technical strategy.
• Champion the shift from traditional development toward agent-orchestrated engineering workflows.
• Align AI initiatives with company vision, product strategy, and client outcomes.

Team Growth & Development

• Lead, mentor, and inspire Senior Engineers and above, fostering a culture of excellence, innovation, and accountability.
• Recruit bar-raising AI-native engineering talent through your network and industry presence.
• Define advanced career growth paths for AI-first engineering roles.

Operational & AI Excellence

• Implement robust agent monitoring, evaluation, and quality-control practices.
• Establish KPIs that measure both engineering productivity and AI agent effectiveness.
• Drive agile and continuous improvement practices that integrate human + AI collaboration.

Execution & Delivery

• Ensure rapid, scalable delivery of solutions orchestrated by agents and sub-agents.
• Oversee requirements, prioritization, sprint planning, backlog management, and documentation with AI-augmented workflows.
• Balance short-term client needs with long-term AI architectural advancements.

Client & Market Alignment

• Develop a deep understanding of Rev.io's SaaS business model and emerging client needs in an AI-first world.
• Ensure solutions deliver business value, scalability, and usability through AI-driven design and execution.

Requirements

• BS in Computer Science or related field, or equivalent professional experience.
• 10+ years in software development and architecture, with proven experience leading senior engineering teams.
• Demonstrated success in AI/ML integration, agentic systems, or large-scale intelligent automation.
• Expertise in leading high-performance technical organizations in fast-paced, results-driven environments.
• Exceptional organizational, prioritization, and leadership skills, with a proven ability to inspire and drive innovation at scale.

Benefits and Perks:

• Generous HSA employer contribution
• 401k with generous company match and immediate vesting
• Unlimited PTO
• Paid Parental Leave
• Company paid for life and disability insurance
• Monthly tech reimbursement
• Monthly fitness reimbursement
• Education and development stipend
• Time off to volunteer at the organization of your choice, as well as company-level volunteer opportunities
• Clear and documented career path for your position
• True open-door policy with opportunities to give feedback to leadership on a continual basis through 1:1 sessions multiple times per year