Principal AI Strategist

One North is a digital experience agency that combines curiosity, scale, and agility to shape the future. As part of TEKsystems, a leading provider of business and technology services, we offer boutique solutions to solve complex problems. Our multidisciplinary teams of strategists, designers, and technologists excel in research and discovery, experience strategy, design, experience management, and technology implementation. Whether clients are establishing a vision for an experience or

optimizing an existing one, we help businesses understand their audiences, design experiences, maximize technology, and bring their digital ideas to life. The world’s most successful companies rely on us to forge the future through electrifying work that sparks innovation and drives results.

Here’s what the opportunity supported through our TEKsystems Global Services (TGS) Talent Acquisition Team requires:

Position Overview

We are seeking a Principal AI Strategist to play a lead role in our AI Innovation team. This position is for an elite professional who combines business strategy acumen, deep AI expertise, presales excellence, and solution development leadership. You will own key strategic client relationships, lead high-stakes pre-sales engagements, drive the creation of AI service offerings, and deliver executive-level AI strategy workshops and other services as required.

This role demands strategic ownership, enterprise-wide influence, and thought leadership both internally and externally. The Principal AI Strategist will directly shape the growth of One North’s and TEKsystems’ AI advisory and solutions portfolio.

This role will ideally be based in the Chicagoland area, but we are open to remote locations across the U.S.

Key Responsibilities

Executive Client Engagement and Leadership:

- Act as the principal advisor on AI strategy for our most strategic customers.

- Lead high-profile executive briefings, advisory sessions, and workshops with C-level client stakeholders and other services or offerings as required.

- Own pre-sales and deal qualification processes for AI engagements, including solution shaping, storytelling, pricing strategies, and securing large-scale engagements.

- Build trusted advisor relationships that position One North as an indispensable strategic partner.

Offering Ownership and Marketing Impact:

- Architect, design, and own new AI offerings and go-to-market strategies across AI strategy, governance, and emerging technologies (e.g., LLMs, Agentic AI, Predictive Analytics).

- Identify emerging AI trends and translate them into new services, solutions, and market opportunities.

- Produce high-impact thought leadership (e.g., white papers, keynote presentations, published articles) to establish One North’s authority in the AI space.

- Act as an external evangelist, participating in select industry forums, panels, and events.

Solution Design and Delivery Leadership:

- Lead the design and delivery of transformative AI strategies, roadmaps, governance frameworks, services, and POCs for Fortune 1000 clients.

- Advise customers on AI platforms and ecosystems (e.g., OpenAI, Claude, Anthropic, LangChain, HuggingFace, Databricks, AWS Bedrock/Sagemaker, Azure OpenAI).

- Ensure AI initiatives drive measurable business outcomes, ethical use, and long-term value.

Organizational Leadership:

- Mentor and guide senior strategists, architects, and consultants across TEKsystems and One North.

- Align business, technical, and executive stakeholders on bold, enterprise-level AI transformation initiatives.

- Foster a culture of excellence, innovation, collaboration, and responsible AI use.

Skills & Qualifications

- 12 or more years of experience in strategy consulting, technology advisory, or innovation leadership roles

- 7 or more years of hands-on AI leadership experience, including:

- Designing enterprise AI strategies, governance frameworks, and AI transformation roadmaps

- Leading presales, solutioning, and deal shaping for AI and emerging tech opportunities

- Deep experience with LLMs, Generative AI, Predictive Analytics, and emerging AI architectures (agentic, composable)

- Proven success delivering high-impact workshops and advisory sessions at the C-level

- Strong business acumen combined with a technical understanding of modern AI stacks

- Exceptional executive presence, communication, and storytelling skills

- Track record of thought leadership, publication, and/or public speaking is highly desirable

- Experience navigating regulatory, ethical, and governance aspects of AI at enterprise scale

Success Metrics

- Growth of AI strategy revenue and AI service line expansion

- Win rate of AI-related pre-sales opportunities and pursuits

- Client satisfaction and executive endorsements

- Thought leadership output (white papers, conferences, industry publications)

- Expansion of internal AI capabilities and talent development