Director, Digital Transformation
Chicago, IL · Hybrid · Permanent
Heads up: this posting is for future opportunities rather than one specific open role. If you apply, we'll add you to our candidate network and may reach out when relevant roles come up.
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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