Jobs › STV

Digital Strategy Lead

STV · Chicago, IL · $132,709–$151,667 a year · Full time

Posted Sep 22, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a digital initiative you carried from concept through adoption. What made people actually use it?

What they are checking: Whether they know that adoption is the hard part and have done the training and follow-through to get it.

Tell me about a time you had to translate between a technical team and a non-technical client.

What they are checking: Whether they can act as the liaison the role describes, making both sides understand each other.

This role is hands-on. How much do you build yourself versus manage specialists who build?

What they are checking: Whether their working style matches a hands-on lead role rather than a purely strategic or managerial one.

What would you do

A program team built its own spreadsheets because the official system was too slow. How would you handle that?

What they are checking: Whether they find out why people work around the system and fix the cause, instead of just forcing compliance.

You're running an executive briefing and a leader challenges the numbers in your dashboard. What do you do?

What they are checking: Whether they stay calm, trace the data and follow up, keeping credibility with senior program leaders.

Several clients and project teams all want their requests done first. How do you decide what to do?

What they are checking: Whether they can manage competing priorities openly, which the posting says this fast-moving role demands.

How would you run a workshop to figure out what reporting a new transportation program owner actually needs?

What they are checking: Whether they can lead discovery that uncovers real decisions, not just list every report someone could ask for.

About the work

You'd support PMIS, reporting and data governance for large infrastructure programs. Tell me about a PMIS or program reporting system you've helped run.

What they are checking: Whether they have real hands-on experience with program management systems, not just a general digital background.

How would you explain the difference between owner-side and contractor-side infrastructure delivery, and why it matters for the tools we build?

What they are checking: Whether they understand owner needs like oversight and reporting, which the posting says the role must know.

How would you set up data governance so that cost and schedule reports from different teams can be trusted?

What they are checking: Whether they understand data ownership, definitions and quality checks, since leaders make decisions from these reports.

What SharePoint workflows or automations have you built, and what problems did they solve?

What they are checking: Whether they can build practical workflow improvements, which the posting names as part of the job.

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The full job description

As published by STV.

STV is seeking a Digital Strategy Lead to join our firm in CA, IL, FL or WI. Responsibilities • Develop management approaches for clients to suit specific governance requirements, efficient and appropriately scaled, using digital tools properly on a strategic or advisory basis or a more tactical implementation and delivery basis. • Find new ways to turn client information into valuable insights and services, aiding the stakeholder engagement process in new ways. • Build and lead a diverse team that’s fully engaged, with strong retention and that builds market position, develops new client relationships, and oversees and leads market pursuits. • Advise clients on program management, delivery strategy, leadership and engagement, vision and outcomes, business case development, establishing governance, structuring a program organization, developing the delivery model, stakeholder management, and employment. Identify new opportunities for working collaboratively on projects. • To establish, foster, and maintain relationships with people at all levels in the business internally and externally. Develop processes and manage downstream contract administration, including Request For Information (RFI’s), submittals, change management, contract closeout, documentation, and claims mitigation with the Program Management team. • Strategize, develop, deploy, and maintain design technology standards and workflows. A broad unique knowledge expertise, uses skills to contribute to development of company objectives and principles and to achieve goals in creative and effective ways. Works on significant and issues and projects requiring an evaluation of intangibles. • Expectations • Exercises independent judgment in methods, techniques and evaluation criteria for obtaining results. Significant coordination among groups. • Occasionally provides consultation and advice to management regarding matters of considerable importance to the functional area. • Exercises independent judgment to occasionally provides direct or indirect supervision to other personnel. • Degreed professional with 10 years related experience. Compensation Range: $132,708.77 - $151,667.16 STV offers the following benefits • Health insurance, including an option with a Health Savings Account • Dental insurance • Vision insurance • Flexible Spending Accounts (Healthcare, Dependent Care and Transit and Parking where applicable) • Disability insurance • Life Insurance and Accidental Death & Dismemberment • 401(k) Plan • Retirement Counseling • Employee Assistance Program • Paid Time Off • Paid Holidays • Back-Up Dependent Care • Parental Leave • Continuing Education Program • Professional Licensure and Society Memberships STV is committed to paying all of its employees in a fair, equitable, and transparent manner. The listed pay range is STV’s good-faith salary estimate for this position. Please note that the final salary offered for this position may be outside of this published range based on many factors, including but not limited to geography, education, experience, and/or certifications. Not sure this role is the perfect match? We encourage you to apply if STV’s work and values resonate with you. We know great candidates don’t always meet every qualification, and research shows women and people of color are less likely to apply unless they do. At STV, we believe strong talent comes from a wide range of backgrounds, and your skills and experience may align with this or another opportunity as we continue to grow.

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