Principal - AI Strategy

Overview

Keystone is a premier economics, technology, and strategy consulting firm built to help companies lead through transformation. Keystone advises technology leaders, Fortune 100 companies, their legal counsel, and governments on business, economic, litigation, and regulatory strategy in relation to innovations and competitive ecosystems. We operate globally from offices in New York City, Boston, San Francisco, Seattle, London, Dubai, and Washington, D.C.

About The Principal – AI Strategy Role

This is not a traditional advisory-only role. We are looking for a leader who combines executive-level strategic judgment with hands-on AI fluency — someone who can identify high-value AI use cases, shape practical roadmaps, guide rapid prototyping, and help clients embed AI into real workflows.

The ideal candidate has led complex AI, digital, technology, analytics, or transformation programs and is comfortable translating between business leaders, technical teams, and operators. Industry depth is welcome but not required; the core requirement is the ability to rapidly understand client environments and drive AI-enabled value across contexts.

• Lead AI Strategy and Transformation Engagements: lead senior client engagements focused on AI strategy, generative AI adoption, agentic workflows, digital transformation, and operating model redesign.
• Identify high-impact AI use cases across business functions, workflows, products, and decision systems.
• Translate ambiguous executive priorities into clear workplans, hypotheses, analyses, solution concepts, and implementation roadmaps.
• Define the business case, value pools, ROI logic, risks, and organizational requirements for AI-enabled transformation.
• Advise senior executives on how AI can reshape cost structures, revenue opportunities, productivity, customer experience, decision-making, and competitive positioning.

• Move beyond strategy decks into prototypes, pilots, workflow redesign, and implementation-ready concepts.
• Partner with technical teams to shape solutions involving LLMs, AI agents, data pipelines, cloud infrastructure, APIs, analytics platforms, and enterprise software ecosystems.
• Help clients evaluate, select, and deploy AI tools in ways that are practical, secure, measurable, and aligned to business goals.
• Design human-in-the-loop processes, governance structures, quality-control mechanisms, and adoption plans for AI-enabled workflows.
• Deliver tangible early value while building toward scalable, enterprise-ready AI capabilities.

• Own senior client relationships, including C-suite and executive stakeholders.
• Lead multi-disciplinary teams across strategy, analytics, technology, product, economics, and operations.
• Develop client-ready narratives that synthesize complex technical, analytical, and strategic findings into clear recommendations.
• Contribute to business development, proposals, thought leadership, and new AI strategy offerings.
• Help define Keystone’s AI-native consulting model and challenge traditional consulting delivery approaches.

What You’ll Bring

• 10+ years of experience in strategy consulting, AI strategy, technology strategy, digital transformation, product strategy, enterprise transformation, analytics, or a related field.
• Demonstrated experience advising senior executives on complex business, technology, or transformation questions.
• Proven ability to identify, prioritize, and deliver high-impact AI or technology-enabled use cases.
• Strong understanding of modern technology architecture, including cloud infrastructure, data pipelines, LLM integration, APIs, and enterprise software ecosystems.
• Hands-on comfort with AI tools, generative AI systems, AI agents, workflow automation, or analytics platforms.
• Track record of acting as a builder, not just an advisor — including prototyping, piloting, implementing, or operationalizing technology-enabled solutions.
• Strong structured problem-solving, analytical rigor, and ability to operate in ambiguous, high-stakes environments.
• Excellent communication and executive presentation skills, with…