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Medium

AI Consulting Director, AI Services

Medium, Chicago, Illinois, United States, 60290

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AHEAD builds platforms for digital business. By weaving together advances in cloud infrastructure, automation and analytics, and software delivery, we help enterprises deliver on the promise of digital transformation.

At AHEAD, we prioritize creating a culture of belonging, where all perspectives and voices are represented, valued, respected, and heard. We create spaces to empower everyone to speak up, make change, and drive the culture at AHEAD.

We are an equal opportunity employer, and do not discriminate based on an individual's race, national origin, color, gender, gender identity, gender expression, sexual orientation, religion, age, disability, marital status, or any other protected characteristic under applicable law, whether actual or perceived.

We embrace all candidates that will contribute to the diversification and enrichment of ideas and perspectives at AHEAD.

Role Overview The AI Engagement Director is a senior consulting leader accountable for the successful delivery of AHEAD’s agentic AI engagements. This role owns the full lifecycle of client transformations, from strategy definition through execution oversight and value realization. The Director works directly with C‑suite and senior stakeholders, shapes vision, aligns teams, removes delivery barriers, and ensures AHEAD delivers measurable, durable outcomes.

This leader blends strategic advisory, program leadership, and hands‑on engagement oversight. They are responsible for making sure the work is delivered, the risks are surfaced and managed, the client experience is exceptional, and the outcomes match what was promised.

Strategic Rationale As enterprises adopt agentic AI at scale, they need senior leadership who can translate strategy into real implementation. This role ensures clients succeed across vision setting, execution, governance, and adoption while maintaining AHEAD’s high bar for delivery excellence.

Role Scope and Focus

Engagement Ownership and Delivery Leadership

Own outcomes for client engagements from design through delivery

Lead day‑to‑day steering, issue resolution, prioritization, and executive alignment

Ensure program governance, risk mitigation, and predictable execution

Strategic Advisory

Guide definition of AI strategy, operating models, and transformation roadmaps

Translate AI capabilities into business outcomes and actionable plans

Executive Engagement

Serve as a trusted advisor to C‑suite leaders

Drive decision‑making, secure alignment, and shape client investment priorities

Oversight of Multi‑Disciplinary Teams

Lead cross‑functional squads across AI engineering, data, cloud, and change management

Ensure quality of deliverables and consistency in method and approach

Shape team structure, expectations, and execution rhythm

Governance, Risk, and Responsible AI

Establish and operationalize governance frameworks

Monitor regulatory shifts, security requirements, and responsible AI best practices

Business Alignment and Value Realization

Define KPIs and track value delivered

Ensure programs generate measurable impact and sustainable adoption

Thought Leadership and Market Presence

Represent AHEAD in client forums and industry events

Produce insights and reusable assets that elevate AHEAD’s positioning

Key Responsibilities

End‑to‑End Engagement Delivery

Lead planning, scoping, staffing, and execution of AI engagements

Conven e steering committees, guide delivery leads, and manage critical risks

Ensure solutions meet business requirements, technical standards, and timeline commitments

Strategy and Roadmap Development

Create enterprise AI strategies, operating models, and implementation plans

Ensure strategies are actionable, measurable, and tied to financial impact

Executive Advisory

Facilitate client decision‑making across use cases, architecture, readiness, funding, and governance

Build and maintain senior relationships and trusted‑advisor credibility

Governance and Risk Management

Operationalize frameworks for responsible AI, compliance, and security

Ensure AI systems meet regulatory and ethical expectations

Cross‑Functional Team Leadership

Lead teams of data engineers, ML engineers, product managers, and change leaders

Drive clarity on roles, deliverables, dependencies, and quality standards

Support talent growth, feedback loops, and performance coaching

Value Realization and Business Impact

Define KPIs, track benefits, and ensure outcomes are delivered and documented

Shape adoption plans with change and OCM teams

Internal Enablement

Contribute to best practices, playbooks, and reusable engagement models

Mentor emerging leaders in consulting craft and client leadership

Must‑Have Qualifications

10 or more years of experience in consulting or enterprise leadership roles focused on AI, analytics, or digital transformation

Strong track record leading complex engagements with ownership of outcomes

Proven ability to manage executive stakeholders, facilitate decisions, and resolve issues at the senior level

Experience guiding AI or technology programs through strategy, design, and delivery

Deep understanding of AI technologies, enterprise data platforms, and modern architectures

Familiarity with responsible AI, governance frameworks, and risk management

Exceptional communication skills and executive presence

Experience leading cross‑functional engineering and product teams

Preferred Qualifications

Experience with AHEAD’s ecosystem: cloud, data, platform engineering, AI platforms

Published thought leadership in AI or digital transformation

Certifications in AI governance, program management, or change management

Experience delivering multi‑agent or agentic automation programs

Environment and Success Metrics

High‑impact engagements with clear and measurable business outcomes

Strong executive feedback and expanded client relationships

Predictable delivery with low escalation rates and high team morale

Well‑defined strategies and roadmaps adopted by client leadership

Repeatable frameworks and playbooks contributed back into AHEAD

Visible market‑facing thought leadership aligned to AHEAD’s brand

$280,000 - $325,000 a year

Why AHEAD: Through our daily work and internal groups like Moving Women AHEAD and RISE AHEAD, we value and benefit from diversity of people, ideas, experience, and everything in between.

We fuel growth by stacking our office with top‑notch technologies in a multi‑million‑dollar lab, by encouraging cross‑department training and development, sponsoring certifications and credentials for continued learning.

USA Employment Benefits include:

Medical, Dental, and Vision Insurance

401(k)

Paid company holidays

Paid time off

Paid parental and caregiver leave

Plus more! See benefits https://www.aheadbenefits.com/ for additional details.

The compensation range indicated in this posting reflects the On‑Target Earnings (“OTE”) for this role, which includes a base salary and any applicable target bonus amount. This OTE range may vary based on the candidate’s relevant experience, qualifications, and geographic location.

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