Principal Consultant

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 builds platforms for digital business. By weaving together advances in cloud infrastructure, automation and analytics, and software delivery, we help enterprises deliver on the promise of digital transformation.

AtAHEAD, we prioritize creating a culture of belonging,where all perspectives and voices are represented, valued, respected, and heard. We create spaces to empower everyone to speak up, make change, and drive the culture at AHEAD.

We are an equal opportunity employer,anddo not discriminatebased onan individual’s race, national origin, color, gender, gender identity, gender expression, sexual orientation, religion, age, disability, maritalstatus,or any other protected characteristic under applicable law, whether actual or perceived.

_ We embraceall candidatesthatwillcontribute to the diversification and enrichment of ideas andperspectives atAHEAD. _

Seasoned customer facing consultant with established leadership skills directing a diverse team of advisory and delivery talent. Provides onsite, hands‑on client engagement management which involves the day‑to‑day running of a client engagement. Helps teams flourish by guiding efforts, directing talents and expanding knowledge and skills to deliver strategic solutions to clients. They are the on‑the‑ground leaders, directing work efforts, analyzing and reviewing proposals from the team, providing appropriate solutions to problems, and making decisions on the way forward by acting as liaisons between the client and the delivery team.

Focused primarily on successful delivery but utilizes their position as a trusted advisor to explore other client needs and working with the team to create proposals to address them. Principal Consultants keep in close contact with clients throughout the duration of the project as part of their official duties.

Responsibilities

• Client Delivery:
• Facilitate strategy, roadmap, design, and planning workshops
• Ensure that customer expectations are appropriately set and managed
• Lead technical project teams in the delivery of consulting service offerings
• Drive and manage the objectives, requirements gathering, project tasks/milestone, project status, dependencies, and timelines, to ensure engagements are delivered successfully and on time while meeting the business objectives
• Breaks down the problem into manageable segments, identifies the factors that affect the problem and decides how to approach the project
• Final editing and sign off on project deliverables
• Presentation of deliverables to client executive management
• Business Development:
• Support business development pursuits through client discovery meetings that help qualify opportunities and allow the ideation of a strawman proposal
• Represent service offerings during the sales cycle, including project scoping, proposal development, and presenting proposals to clients
• Develop and promote relationships with customers and present technical solutions to C-Level executives
• Practice Development & Thought Leadership:
• Develop and enhance AHEAD Advisory services offerings, including consulting offerings and deployment services
• Technology thought leader and evangelist
• Maintain a broad knowledge and understanding of the current and anticipated future state of the IT marketplace including IT trends, technologies, and standards
• Mentor to team members

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

Why AHEAD:

Through our daily work and internal groups like Moving Women AHEAD and RISE AHEAD, we value and benefit from diversity of people, ideas, experience, and everything in between.

We fuel growth by stacking our office with top‑notch technologies in a multi‑million‑dollar lab, by encouraging cross department training and development, sponsoring certifications and credentials for continued learning.

USA Employment Benefits include:

• Medical, Dental, and Vision Insurance
• 401(k)
• Paid company holidays
• Paid time off
• Paid parental and caregiver leave
• Plus more! See benefits https://www.aheadbenefits.com/ for additional details.

The compensation range indicated in this posting reflects the On‑Target Earnings (“OTE”) for this role, which includes a base salary and any applicable target bonus amount. This OTE range may vary based on the candidate’s relevant experience, qualifications, and geographic location.