Lead Digital Strategy Manager (Digital Strategy)

TL;DR

Lead Digital Strategy Manager (Project Management): Strategizing and executing complex cross-functional digital initiatives for Cat Digital with an accent on operational rhythms and stakeholder alignment. Focus on translating strategic objectives into actionable roadmaps and ensuring structured oversight of digital projects to completion.

Location: Must be based in Chicago or Peoria, Illinois, USA

Salary: $128,470 - $192,710

Company

Cat Digital is the digital and technology arm of hirify.global Inc., leveraging data, advanced analytics, and AI to build industry-leading digital solutions for customers and dealers.

What you will do

• Manage day-to-day project delivery activities, coordinating stakeholder alignment, communications, and change readiness.
• Translate strategic objectives into actionable roadmaps, aligning long-term vision with near-term execution.
• Develop contingency plans for delivery, dependency, and adoption risks, escalating issues with clear business and technical impacts.
• Maintain a cohesive operating rhythm to align cross-functional teams around shared outcomes and resource allocations.
• Monitor project results and adherence to quality standards, incorporating stakeholder feedback into delivery adjustments.
• Champion a culture of strategic thinking to connect daily execution with broader business impact.

Requirements

• Extensive experience in program/project management including charters, scheduling, scope, risk, and governance.
• Proven ability to engage stakeholders and collaborate across business, product, and engineering functions.
• Strong leadership presence with the ability to motivate teams and drive momentum in ambiguous situations.
• Knowledge of tactical and strategic planning techniques (short-term to 5-year horizons).
• Visa Sponsorship is not available for this position.
• Must be located in the USA (Chicago or Peoria, IL).

Nice to have

• Experience building or refining delivery processes aligned to PMO standards.
• Strong storytelling skills to synthesize complex information into compelling narratives.
• Proven ability to lead through organizational shifts and drive adoption of new tools or processes.

Culture & Benefits

• Comprehensive medical, dental, and vision benefits.
• 401(k) savings plans, Health Savings Account (HSA), and Flexible Spending Accounts (FSAs).
• Paid time off including vacation, holidays, and volunteer days.
• Tuition reimbursement and continuous career development opportunities.
• Parental leave and adoption benefits.