Director, Digital Transformation

Axial Search; Chicago (IL); On-site; USD 190,000 - 420,000; Full time

Job summary

Axial Search is a specialist executive search firm focused on leaders who guide organizations through AI transformation. We track market trends and provide tools including a live job market dashboard with salary and hiring data across AI roles.

The market shows 300+ senior digital transformation postings with compensation ranging from $190K to $420K annually, highlighting the demand for strong leadership and enterprise-scale modernization experience.

Qualifications

• 10+ years in digital transformation, enterprise modernization, operations, or strategy roles.
• At least 5 years leading teams at the director level or equivalent.
• Strong technical literacy: enterprise architecture, cloud platforms, data integration, and modern app development.
• Experience with change management, organizational design, and building high-performing teams in matrix environments.
• Track record of managing complex P&Ls and communicating ROI.

Responsibilities

• Own the strategy and roadmap for digital transformation across the organization, identifying high-impact initiatives.
• Lead cross-functional teams to design and execute multi-year modernization programs.
• Partner with CTO/CIO and leaders to assess legacy systems and cloud strategies.
• Build and mentor a team of transformation managers, architects, and analysts; establish governance.
• Communicate progress, risks, and ROI to the executive team and board; own the business case.
• Drive organizational change management—defining operating models and embedding continuous improvement.
• Oversee vendor relationships and external partnerships critical to transformation delivery.

Skills

Digital transformation

Enterprise modernization

Leadership

Cross-functional collaboration

Strategic planning

Tools

Cloud platforms

Enterprise architecture

Job description

Axial Search is a specialist executive search firm built for one kind of hire: leaders who help organizations navigate AI transformation.

Visit our website to learn more about our process and explore free tools for your job search, including our live job market dashboard with salary, skills and hiring trend data from thousands of AI transformation roles.

What The Market Looks Like

We’ve tracked 300+ senior-level digital transformation postings across the US in the last six months, with concentrated hiring in Texas, California, and New York — though Chicago remains a strong hub for this work. These roles span professional services, financial services, manufacturing, healthcare, and technology sectors. Compensation for this cohort typically lands between $190K and $420K annually. The strongest candidates bring hands‑on experience leading large-scale modernization initiatives, deep fluency with enterprise technology stacks, and the ability to translate technical complexity into business outcomes for C-suite and board audiences.

Job Responsibilities

• Own the strategy and roadmap for digital transformation across the organization, identifying high-impact initiatives that align with business objectives and competitive positioning
• Lead cross-functional teams (technology, operations, finance, business units) to design and execute multi-year modernization programs, ensuring alignment on priorities and milestones
• Partner with the CTO, CIO, and business leaders to assess legacy systems, evaluate cloud migration strategies, and recommend technology investments that reduce technical debt
• Build and mentor a team of transformation managers, architects, and analysts; establish governance, accountability, and best-practice frameworks
• Communicate progress, risks, and financial impact to the executive team and board; own the business case and ROI tracking for transformation initiatives
• Drive organizational change management — defining new operating models, upskilling talent, and embedding a culture of continuous improvement and innovation
• Oversee vendor relationships, third-party integrations, and external partnerships critical to transformation delivery

Candidate Requirements

• 10+ years in digital transformation, enterprise modernization, operations, or strategy roles; at least 5 years leading teams at the director level or equivalent
• Proven track record designing and delivering large-scale technology transformations (cloud migration, legacy system replacement, process automation) with measurable business impact
• Strong technical literacy: comfortable discussing enterprise architecture, cloud platforms, data integration, and modern application development with technical teams
• Demonstrated ability to influence across silos — building trust with C-suite, IT leadership, and business units to align on vision and drive execution
• Experience with change management, organizational design, and building high-performing teams in matrix or matrixed environments
• Track record of managing complex P&Ls and communicating ROI; comfort with financial modeling and business case development