Ken Judy

I'm a Senior Partner at Stride, combining strategic leadership with hands-on development to modernize legacy systems using AI and advanced compiler technology. Based in New York, I help organizations address the common problem where AI pilots fail to deliver meaningful ROI within the agreed timeframe.

"I believe in responsible development practices that benefit both organizations and the people who build and maintain software over time."

My work focuses on moving teams beyond adoption metrics toward actual business outcomes, building practical governance approaches that scale. I use a structured Plan-Do-Check-Act approach for AI code generation that brings proven quality practices to human-AI collaboration.

As a CTA certified coach, I mentor technical leaders on practical AI adoption and help teams avoid common implementation pitfalls. I'm also a contributor to peer-reviewed publications on agile values and innovative methodologies, with certifications in software development, Scrum, and information privacy.

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Background

My career spans over two decades in technology leadership, from hands-on software development to C-suite executive roles. I've led transformations at organizations ranging from mid-size consultancies to major media companies.

Recent Work

At Stride, I design and implement responsible AI solutions integrated with advanced compiler technology to solve critical .NET modernization challenges. I've led enterprise modernization of complex legacy systems (1000+ assemblies), achieving 25% reduction in analysis time while maintaining verifiable accuracy.

Key achievements include integrating Roslyn Compiler analysis with GPT-4 and Claude, developing the Plan-Do-Check-Act framework for AI code generation, and building AI adoption assessment methodologies that help organizations move from pilot phases to measurable business outcomes.

Leadership Experience

During four years leading Stride's Leadership Team (two years as CEO, two as COO), we maintained profitability during the COVID-19 pandemic, shifted from staff augmentation to team-based projects, transitioned to remote-first operations, and reframed our core values with consent of the entire organization.

I increased transparency through health dashboards of financial, sales, and hiring metrics. We fostered equity through pay bands and capability matrices, supported well-being through progressive expense and leave policies, and raised morale as measured by NPS and engagement surveys.

Prior Experience

As Chief Technology and Product Officer at The Daily Beast, I transformed the product and technology organization, replacing a legacy Java-based CMS with modern Node.js/React.js services. This eliminated $1M in licensing costs, contributed to 30-50% increase in ad revenue, and reduced publishing time from an hour to minutes.

At Simon & Schuster, I led strategic consumer digital initiatives and evangelized iterative software development practices. I championed tools for enriching book metadata that increased discoverability and facilitated promotions, enabling the company to increase direct consumer annual revenue by an order of magnitude over three years.

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Values

Throughout my career, I've been guided by a consistent set of principles that inform how I work with teams and organizations:

"Do what you say and say what you mean, respect people, help others, practice humility, and learn."

Transparency. I believe in sharing essential performance measures openly and communicating changes as soon as they're well-formed. Transparency builds trust and enables teams to make informed decisions.

Accountability. Real accountability comes from empowering individuals, removing obstacles, recognizing domain expertise, and organizing into cross-functional, self-organizing teams.

Learning. I constantly learn and step well out of my comfort zone. The best solutions come from curiosity, experimentation, and willingness to be proven wrong.

Equity. Everyone deserves fair treatment, clear expectations, and opportunities for growth. I've championed pay bands, capability matrices, and inclusive policies throughout my leadership roles.

Sustainability. Technology should advance people, profit, and planet. I focus on practices that create lasting value rather than short-term wins that leave teams burned out or systems unmaintainable.

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Experience Highlights

Technical Expertise

  • .NET/Roslyn static analysis and compiler technology
  • ANTLR SQL parsing and business rule extraction
  • Azure OpenAI/GPT-4 and Anthropic Claude integration
  • Governance frameworks for responsible AI adoption
  • Legacy system modernization and refactoring
  • Agile software development and XP practices

Certifications

  • Certified Software Development Professional (CSDP)
  • Certified Scrum Professional - ScrumMaster & Product Owner
  • CTA Certified Coach, an ICF Accredited Training Program
  • Data Ethics, AI and Responsible Innovation
  • Certified Information Privacy Professional - United States (CIPP/US)

Publications

  • Agile Principles and Agile Conduct
  • Agile Values, Innovation and the Shortage of Women Software Developers
  • Great Scrums Need Great Product Owners: Unbounded Collaboration and Collective Product Ownership
  • Ript: Innovation and Collective Product Ownership
  • Using Agile Practices to Spark Innovation in a Small to Medium Sized Business

Education

BA in Mathematics-Physics and Theater from Whitman College

Beyond Technology

Before my technology career, I spent eight years as an Artistic Associate at Annex Theatre in Seattle, producing forty developmental workshops and collaborating with playwrights, directors, and actors. This experience taught me about collaboration, creative problem-solving, and the importance of creating safe spaces for experimentation—lessons that have served me well in technology leadership.

Let's Connect

If you're interested in discussing AI adoption, legacy system modernization, or leadership development, I'd be happy to connect. I'm always open to conversations about how we can build better software and better organizations.