Director, Digital Transformation

Axial Search is a specialist executive search firm built for one kind of hire: leaders who help organizations navigate AI transformation. Apply today to express your interest in roles like this one. 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 positioningLead cross-functional teams (technology, operations, finance, business units) to design and execute multi-year modernization programs, ensuring alignment on priorities and milestonesPartner with the CTO, CIO, and business leaders to assess legacy systems, evaluate cloud migration strategies, and recommend technology investments that reduce technical debtBuild and mentor a team of transformation managers, architects, and analysts; establish governance, accountability, and best-practice frameworksCommunicate progress, risks, and financial impact to the executive team and board; own the business case and ROI tracking for transformation initiativesDrive organizational change management — defining new operating models, upskilling talent, and embedding a culture of continuous improvement and innovationOversee 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 equivalentProven track record designing and delivering large-scale technology transformations (cloud migration, legacy system replacement, process automation) with measurable business impactStrong technical literacy: comfortable discussing enterprise architecture, cloud platforms, data integration, and modern application development with technical teamsDemonstrated ability to influence across silos — building trust with C-suite, IT leadership, and business units to align on vision and drive executionExperience with change management, organizational design, and building high-performing teams in matrix or matrixed environmentsTrack record of managing complex P&Ls and communicating ROI; comfort with financial modeling and business case development