Senior AI-Driven Design Strategist

Highland US; Chicago (IL); Hybrid; USD 140,000 - 155,000; Full time

Benefits offered by this job

Health insurance

Dental + Vision

401k retirement plan

Paid time off

Learning stipend

Parental leave

Disability insurance

Life insurance

Job summary

Highland is a Chicago-based digital product and innovation consultancy seeking a Lead Designer & Strategist. This client-facing role blends strategic design, product leadership, and AI-enabled methods to drive end-to-end delivery.

You will lead cross-functional teams, mentor designers, and shape roadmaps with client principals. The role emphasizes collaboration, storytelling, and measurable business outcomes in a fast-paced environment.

Qualifications

• 10+ years in product strategy, UX, and strategic design.
• 6+ years in a consulting environment.
• Proven experience leading multidisciplinary teams and client engagements.
• Masters degree or equivalent in Design, HCI, or related field.
• Strong communication, facilitation, and storytelling skills.

Responsibilities

• Lead the creation of product, service, and ecosystem strategies that connect insights, business priorities, and tech opportunities.
• Extend strategic design into product definition with roadmaps and criteria.
• Translate insights into clear business opportunities and strategic recommendations.
• Use AI-enabled design and production methods to accelerate learning and delivery.
• Lead cross-functional teams and guide client decisions to ensure value delivery.
• Mentor designers and advance Highland’s capabilities in strategic design leadership.

Skills

Strategic design

AI-enabled design

Client engagements

Cross-functional leadership

Facilitation

Storytelling

Education

Masters degree in Design or HCI

Tools

Miro

Figma

Job description

Highland is a Chicago-based digital product and innovation consultancy seeking a Lead Designer & Strategist. This client-facing role blends strategic design, product leadership, and AI-enabled methods to drive end-to-end delivery.

You will lead cross-functional teams, mentor designers, and shape roadmaps with client principals. The role emphasizes collaboration, storytelling, and measurable business outcomes in a fast-paced environment.