Lead Designer – Strategist

Highland

Lead Designer & Strategist integrating strategic design and AI tools at a product consultancy in Chicago. Overseeing multidisciplinary teams to deliver quality client-centered outcomes.

Posted 4/11/2026full-timeChicago • Illinois • 🇺🇸 United StatesSenior💰 $135,000 - $150,000 per yearWebsite

About the role

Key responsibilities & impact

Lead the creation of product, service, and ecosystem strategies that connect human insight, business priorities, and technological opportunity into clear, actionable directions.
Extend strategic design into product definition, helping clients & teams articulate value, weigh effort, and prioritize tradeoffs.
Ensure decisions & direction remain grounded in evidence by supporting generative research, and guiding evaluative & secondary research.
Use AI-enabled design & production methods to accelerate exploration, prototyping, building, and learning.
Lead cross-functional teams through complex work with clarity, credibility, and discipline.
Contribute to the growth of Highland’s design & product practice by strengthening people, points of view, and market presence.

Requirements

What you’ll need

10+ years of experience in product strategy, UX, & strategic design
Proven experience leading multidisciplinary teams and client engagements
Strong experience translating opportunities into product & service strategies
Familiarity with product discovery, definition, roadmaps
Experience with modern, collaborative design tools such as Miro & Figma
Experience with AI-enabled design & production workflows is highly valued
Exceptional communication, facilitation, and storytelling skills
Masters degree or equivalent experience in Design, HCI, or related field

Benefits

Comp & perks

N/A 📊 Check your resume score for this job Improve your chances of getting an interview by checking your resume score before you apply. Check Resume Score

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

product strategyUXstrategic designproduct discoveryproduct definitionproduct roadmapsAI-enabled designproduction workflows

Soft Skills

communicationfacilitationstorytellingleadershipclaritycredibilitydiscipline

Certifications

Masters degree in DesignMasters degree in HCI