Director, Digital Strategy

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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