Principal - AI Strategy

 

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.  

 

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Key Responsibilities 

 

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. 
   

Build, Prototype, and Deliver Practical AI Solutions  

• 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. 

 

Drive Client Leadership and Commercial Impact  

• 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. 

 

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What You’ll Bring 

 

Required 

• 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 the ability to translate technical complexity into business implications.  

• Experience leading teams, managing client relationships, and owning engagement delivery from scoping through execution.  

• Commercial orientation, including experience supporting business development, proposal development, account growth, or practice-building. 
   

Preferred 

• Experience building or operating within an AI-native business, AI product environment, venture-backed company, technology firm, or advanced analytics team.  

• Exposure to agentic AI systems, RAG, LLM orchestration, AI copilots, workflow automation, or human-in-the-loop AI design.  

• Experience across multiple industries or business functions.  

• Experience with enterprise AI governance, model risk, data governance, privacy, security, change management, or responsible AI.  

• Background in consulting, product, engineering, data science, economics, business analytics, or a related quantitative field.  

• MBA, advanced technical degree, or equivalent professional experience. 
   

What Sets You Apart 

• You are a strategy leader who can build.  

• You can earn credibility with executives, technical teams, and frontline operators.  

• You move quickly from ambiguity to structure, from strategy to prototype, and from prototype to business impact.  

• You understand AI as a business transformation tool, not just a technology trend.  

• You are intellectually rigorous, commercially sharp, and comfortable challenging legacy consulting models.  

• You can operate across industries without needing a narrow sector playbook. 

 

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Why Join Us 

• Shape a differentiated AI Strategy practice at a moment when AI is redefining how organizations compete, operate, and create value. 

• Work at the frontier of AI-enabled transformation, workflow redesign, and new operating models across complex client environments. 

• Partner with exceptional colleagues across technology, economics, management science, strategy, and AI implementation. 

• Lead high-impact engagements where practical AI adoption can change how critical work gets done — from strategy through execution. 

 

Why Join Us 

• Shape a differentiated AI Strategy practice serving legal sector clients at a moment of structural change. 

• Work at the frontier of legal AI, workflow transformation, and professional-services operating model redesign. 

• Partner with exceptional colleagues across technology, economics, management science, law, and strategy. 

• Lead high-impact engagements where practical AI adoption can change how legal work is delivered.