Overview
Senior Vice President, Engineering & AI Transformation
Chicago, IL | Reports to Chief Product & Technology Officer
The Opportunity
Our client is entering a defining phase of growth as it scales beyond $1B in revenue. Technology is central to this evolution, powering customer-facing platforms, mission-critical internal systems, and data-driven capabilities that directly impact revenue, operational performance, and customer experience.
We are seeking a transformational Senior Vice President of Engineering & AI Transformation to lead the next chapter of engineering scale, modernization, and intelligent automation across the enterprise.
This is a true ownership mandate.
Reporting directly to the Chief Product & Technology Officer, this executive will define how engineering operates at scale, elevate execution rigor, guide platform evolution, and embed AI capabilities aligned to measurable business value.
Scope & Impact
The SVP will lead and evolve a growing, multi-layer engineering organization that includes senior leaders, managers, and distributed teams. This role owns engineering strategy and delivery across multiple product lines and enterprise platforms.
Key areas of leadership include:
Enterprise Engineering Strategy & Delivery
Own end-to-end engineering execution across software development, architecture, platform, and quality
Establish a scalable operating model that drives predictable, high-confidence delivery
Elevate governance, estimation discipline, and executive-level visibility
Architecture, Platform & Modernization
Guide platform evolution to ensure scalability, resilience, and long-term maintainability
Lead modernization initiatives while balancing innovation with operational stability
Champion cloud-native engineering and DevOps best practices
AI & Intelligent Automation
Partner with Product and Data leaders to prioritize AI and GenAI use cases grounded in business impact
Drive responsible, secure AI adoption across products and internal workflows
Establish scalable governance frameworks for experimentation and deployment
Organization & Culture
Design and scale a high-performing engineering organization aligned to business growth
Build leadership bench strength and clear accountability structures
Foster a culture grounded in ownership, technical excellence, and continuous improvement
Executive Partnership
Serve as a trusted partner to executive stakeholders and cross-functional leaders
Translate complex technical realities into clear business decisions
Operate with high visibility across senior leadership
What We’re Looking For
15+ years of progressive software engineering experience with senior leadership responsibility
Proven ownership of enterprise-level engineering delivery outcomes
Experience leading and scaling mid-to-large engineering organizations, including distributed or global teams
Strong foundation in modern engineering practices, cloud-native platforms, and DevOps operating models
Experience modernizing complex environments
Executive-level communication skills and strong cross-functional influence
Experience in high-growth or transformation-driven environments is highly valued. Exposure to AI-enabled product initiatives tied to measurable business outcomes is a plus.
What Success Looks Like
Within the first year, this leader will:
Establish engineering as a predictable, trusted execution partner
Introduce scalable operating standards and executive-level reporting visibility
Strengthen platform reliability and operational maturity
Build a durable leadership bench and scalable organizational structure
Advance AI initiatives aligned to tangible business value
Location
This role is based in the bustling neighborhood of Fulton Market in Chicago with a regular on-site executive presence expected.
Compensation
Executive compensation package includes a competitive base salary starting at $250K+, performance-based bonus, and comprehensive benefits.
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