Senior Advisory Consultant - Digital Transformation & Delivery

AHEAD; Chicago (IL); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Medical Insurance (US)

Dental Insurance

Vision Insurance

401(k)

Paid holidays

Paid time off

Parental and caregiver leave

Job summary

AHEAD is seeking a seasoned client-facing consultant in Chicago to lead advisory and delivery engagements, guiding diverse teams to implement strategic IT modernization. You will manage day-to-day client engagement activities and serve as a trusted advisor on expanding services with clients.

Responsibilities include delivering strategy workshops, leading delivery teams, shaping proposals, and mentoring colleagues while maintaining executive relationships and driving business growth.

Qualifications

• Senior-level consulting experience.
• Minimum 15 years of experience as senior information technology leader overseeing transformative modernization initiatives (e.g., cloud adoption, automation, platform engineering, agile-at-scale adoption).
• Strong understanding of business measurement frameworks (e.g., OKRs).
• Familiarity with Agile methodologies and Software Development Lifecycle principles.
• Minimum of five years of executive technology consulting experience.
• Undergraduate degree in Computer Science, Mathematics, or similar discipline.
• Excellent verbal and written communication skills.
• Demonstrated Business Acumen.
• Ability to solve complex, abstract problems.
• Excellent interpersonal skills, good listener, ability to connect with different personalities.
• Executive presence.
• Demonstrated experience as a technology change agent.
• MBA is a plus.

Responsibilities

• Facilitate client strategy, roadmap, design, and planning workshops.
• Ensure that customer expectations are appropriately set and managed.
• Lead technical project teams in delivering consulting offerings.
• Drive and manage objectives, requirements gathering, tasks/milestones, dependencies, and timelines to deliver engagements on time.
• Breaks down problems into manageable segments and decides how to approach the project.
• Final editing and sign-off on project deliverables.
• Presentation of deliverables to client executive management.
• Support business development pursuits through client discovery meetings and strawman proposals.
• Represent service offerings during sales cycles, including scoping, proposal development, and presenting proposals to clients.
• Develop and promote relationships with customers and present technical solutions to C-Level executives.
• Develop and enhance AHEAD Advisory services offerings and deployment services.
• Act as technology thought leader and evangelist within the organization.
• Maintain knowledge of current and future IT marketplace trends, technologies, and standards.
• Mentor to team members.

Skills

Senior-level consulting experience

Executive technology consulting

Excellent verbal and written comms

Executive presence

Business acumen

Problem solving

Interpersonal skills

Education

Bachelor's degree in Computer Science, Mathematics, or related field

MBA (preferred)

Job description

AHEAD is seeking a seasoned client-facing consultant in Chicago to lead advisory and delivery engagements, guiding diverse teams to implement strategic IT modernization. You will manage day-to-day client engagement activities and serve as a trusted advisor on expanding services with clients.

Responsibilities include delivering strategy workshops, leading delivery teams, shaping proposals, and mentoring colleagues while maintaining executive relationships and driving business growth.