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Planning Director

STV · Chicago, IL · $164,279–$187,748 a year · Full time

Posted Jun 11, 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 your relationships with agencies like IDOT, CTA, Metra or the City of Chicago. What work have you done with them?

What they are checking: Whether they bring real local client relationships, which this growth role depends on.

Tell me about a planning team you built or grew. How did you hire and develop people?

What they are checking: Whether they can build and mentor a high-performing local team, a central part of the role.

Where do you see the biggest planning opportunities in the Chicago region over the next five years?

What they are checking: Whether they have a real view of the local market to shape STV's long-term strategy here.

How do you work with other STV offices nationally to bring in expertise you do not have locally?

What they are checking: Whether they will use the firm's national resources to win and deliver bigger work.

What would you do

Your team is overloaded with current work, and a big pursuit just came out. What do you do?

What they are checking: Whether they can balance delivery and growth without letting either suffer.

A client is unhappy with a study's draft recommendation because of community pushback. How do you handle it?

What they are checking: Whether they can manage public and political pressure while keeping the analysis credible.

How do you decide which pursuits are worth chasing and which to pass on?

What they are checking: Whether they make disciplined go or no-go decisions that protect the practice's win rate.

About the work

How would you go after a large on-call planning contract with a public agency?

What they are checking: Whether they understand the public procurement and positioning that win on-call contracts.

Walk me through how you would structure an alternatives analysis for a new transit corridor.

What they are checking: Whether they can lead the technical work as project manager or principal, not just sell it.

How do environmental reviews such as NEPA shape a planning study's schedule and approach?

What they are checking: Whether they know how federal environmental processes drive planning decisions and timelines.

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The full job description

As published by STV.

Planning Director – Transportation Planning (Chicago, IL) Lead Growth. Shape the Future of Transportation. STV is seeking a Planning Director to lead and grow our Transportation Planning Practice in Chicago. This is a high-impact leadership role focused on expanding market presence, building client relationships, and delivering complex planning programs across the region. Your Impact • Drive growth with key clients including IDOT, CTA, Metra, and City of Chicago • Lead major pursuits, on-call contracts, and strategic planning initiatives • Serve as PM/Principal on feasibility studies, alternatives analyses, and environmental reviews • Build and mentor a high-performing local planning team • Shape STV’s long-term planning strategy in Chicago What You Bring • 10+ years in transportation planning • Strong client relationships and BD experience • Expertise in planning studies and project delivery • Experience with public agencies (federal, state, local) • AICP or PE required Why STV • Lead a growing Midwest planning practice • Influence high-profile infrastructure investments • Advance your career through leadership opportunities and national collaboration Compensation Range: $164,279.49 - $187,747.98 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 (starting at 16 days) • Paid Holidays (9 days) • Back-Up Dependent Care (up to 10 days per year) • Parental Leave (up to 80 hours) • 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.

Apply at STV