Axial Search recruits for AI transformation roles across North America, building long-term relationships with leaders across every industry vertical. Apply today to express your interest in this position and others like it. Visit our website to learn more about our process and to find free tools to support 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

Director-level digital strategy roles are hiring heavily across financial services and professional services right now, with a clear focus on building out AI-native customer and operations capabilities. In the Chicago market specifically, regional banks, insurance carriers, and specialty finance firms are all investing in next-generation platforms. Base compensation for director-level digital strategists in financial services generally lands in a $170K–$260K range, and the strongest directors we place are those who can operate jointly with the CIO and the CMO without getting crushed between them.

Job responsibilities

Own the firm's digital strategy across customer, operations, and product surfaces
Lead a team of digital strategists, experience designers, and analysts
Partner with the CIO, CMO, and business-line leadership on execution and investment
Drive market, customer, and competitive analysis that informs senior-level decisions
Set multi-year investment priorities for digital and AI-enabled capabilities
Represent digital strategy in exec and board-level forums
Own the strategic roadmap for customer-facing digital experiences
Build the analytical muscle that keeps the digital investment grounded in evidence

Candidate requirements

10+ years in digital strategy, consulting, or senior in-house roles
Direct financial services (banking, insurance, or capital markets) experience strongly preferred
Proven ability to influence senior leaders on multi-year investment decisions
Strong leadership track record — hiring and developing senior individual contributors
Excellent executive communication
Fluent across modern digital, data, and AI capabilities

Director, Digital Strategy