Senior Director, AI & Digital Transformation

APCO•Chicago, IL

1d•$215,000 - $260,000•Remote

About The Position

Are you a visionary? Someone who explores the intersection between transformation and technology? Do you have a passion for leading clients through the unknown while pushing the boundaries of what is possible as a leader? Then we have the opportunity for you! Gagen is seeking a Sr. Director, AI & Digital Transformation to serve as a senior counselor and a primary point of contact with clients, while helping the firm grow by generating new business opportunities, and lead a cross-functional team of talented consultants . This is a senior level consulting role for someone who has passion for AI and Digital Transformation readiness and adoption strategies that help organizations navigate the complex balance between technical implementation and the human struggle of change. This role is responsible for leading adoption of AI and digital transformation strategies (helping companies integrate AI and other digital technologies to enhance business operations and modernize processes through associated change management and organizational effectiveness solutions), business development and client management. The ideal candidate will have a strong background advising IT and technology executives, experience with enterprise technology adoption, and a proven ability to bridge operational change with technical execution. This person will also help shape go-to-market strategies and represent Gagen MacDonald in high-stakes client engagements. The job can be based at one of our U.S. offices (Chicago, NYC, DC, Raleigh) or a home office, and it requires some travel to client sites and company meetings.

Requirements

15+ years of experience in change management and communications, digital transformation, or a related field, with direct experience supporting change in technology implementations.
Demonstrated experience leading AI-driven change initiatives in large organizations.
Deep familiarity with Microsoft enterprise products and AI tools (Co-pilot, SharePoint, Power Apps, etc.); hands-on experience preferred.
Strong business development and client relationship management skills.
Exceptional ability to communicate complex AI concepts to non-technical audiences, clients, and executive leadership. Ability to build consensus and drive adoption across diverse teams.
Familiarity with AI governance frameworks, regulatory requirements (e.g., GDPR, EU AI Act), and best practices for responsible AI deployment. Experience developing and implementing responsible AI policies in a corporate setting.
Experience working in or with communications/change management teams is a plus.
Excellent written and verbal communication skills.
Proven ability to deliver results in fast-paced, high-stakes environments.
At least 5+ years of corporate, agency or consulting experience in strategic communication roles with a focus on technology and digital transformation. Experience consulting with global Fortune 500 corporations is preferred.
Bachelor’s degree in communications, organizational effectiveness, technology, or related field; or equivalent combination of education, experience and training. Advanced degree a plus.
Experience working both independently and collaboratively while partnering across organizational functions.
Experience building relationships and business by identifying and pursuing new opportunities with clients.
Experience navigating large, complex organizations working with the C-suite and senior leaders including technology professionals.
A large professional network that can be leveraged to grow Gagen’s market-share.

Responsibilities

Develop and own Gagen's AI Go-To-Market (GTM) strategy to drive revenue-generating AI offerings in partnership with client leads.
Build a comprehensive roadmap and strategy for AI readiness, implementation and adoption aligned with the firm’s business objectives and client needs.
Lead the identification, prioritization and execution of AI initiatives across service lines, including client solutions, internal operations and new product development.
Drive business development, prospecting and sales efforts, targeting large enterprise clients.
Contribute to the firm's growth by generating new business and leading the development of proposals and RFP responses for multi-disciplinary engagements with new clients.
Monitor and report on the performance and impact of AI initiatives, adjusting strategy as needed to maximize value and mitigate risk.
Monitor and analyze broader trends and drivers of change impacting AI adoption and organizational effectiveness—such as technological innovation, demographic shifts, regulatory developments, and evolving consumer values—to enable our clients to anticipate shifts in their operating environment and shape transformation strategies and roadmaps to position and capitalize on new opportunities or mitigate emerging risks.
Advise our clients on AI change and communications strategies and solutions to translate complex AI concepts into compelling narratives the drive AI adoption, and ensure that our offerings remain at the forefront of industry innovation.
As Senior Director of AI & Digital Transformation, enable clients to set their strategic direction for AI transformation and integration, and ensure that AI initiatives are value drivers for the organization and encompass change readiness plans.
Advise C-level executives on the strategic implications and potential value of AI implementation as it relates to the employee experience, talent retention and growth, reputational risk and the trends impacting these areas.
Drive readiness and adoption strategies for end-to-end delivery of large, complex AI projects, including defining business requirements, developing solutions, implementing readiness and adoption plans, changing communication strategy and managing project execution.
Lead project and/or account management activities to ensure execution on client requirements, managing teams on multiple projects and/or multi-disciplinary workstreams for projects of high complexity, size, and/or scale.
Responsible for revenue and sales targets at the senior director level.
Serve as a subject matter expert in client meetings, able to “speak technology” and communicate effectively with CIOs, CTOs and operational leaders.
Represent the firm in industry forums, conferences and with clients as a thought leader in AI and digital transformation; be an outspoken advocate for Gagen’s human-centric approach to AI and digital transformation.
Use your deep knowledge and mastery of technical skills to be regarded as an expert in your discipline by the client and your colleagues.
Build and manage a cross-functional team of AI and digital transformation consultants dedicated to adoption, change readiness and organizational effectiveness.
Foster a culture of innovation, continuous learning and responsible AI adoption throughout the organization.
As part of the senior leadership team, collaborate with other leaders to integrate AI into the firm’s overall strategic plan.