Lead Designer & Strategist

Highland • Chicago, IL

8d • $135,000 - $150,000 • Hybrid

About The Position

Highland is a digital product & innovation consultancy based in Chicago. For more than 25 years, our team of researchers, strategists, designers, and engineers has helped mission-driven organizations and customer-centric companies design and launch digital products that matter – turning uncertainty into opportunities for growth.

We refer to what we design as Experiences that Matter: digital products & services that improve people’s lives while advancing organizational goals. We partner with mid-market services organizations, membership-based institutions, and enterprise innovation teams.
Our work is grounded in Human Flourishing, inspired by research from Harvard University’s Institute for Quantitative Social Science. Our values—People First, Give a Damn, Be Curious, and Be Transparent—are expectations we hold ourselves and each other to every day.

Highland assembles lean, focused teams to research & set strategy, design solutions, and engineer products that deliver value for our clients and their customers. Increasingly, we utilize genAI to accelerate our teams, allowing our practitioners to focus energy on the things that matter most, and make our offering available to a wide range of organizations.

The Lead Designer & Strategist is a critical role, leading & taking responsibility for strategic & complex projects from start to finish.

The Lead Designer & Strategist is a role that blends:
Strategic design & product strategy
AI-enabled design & product leadership

This client-facing role is for an experienced, consultative designer, who has a generalist mindset, has incorporated product management into their practice, and uses AI-assisted tools to accelerate learning, reduce time to market, and oversee the delivery of working software.
You will lead work independently, partner closely with a client principal, and collaborate with research, design, engineering, and strategy teammates to lead end-to-end delivery of high-quality, business-conscious outcomes.

Requirements

• 10+ years of experience in product stragety, 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
• Exceptional communication, facilitation, and storytelling skills
• Masters degree or equivalent experience in Design, HCI, or related field

Nice To Haves

• Experience with AI-enabled design & production workflows is highly valued

Responsibilities

• Strategic Design Leadership: Lead the creation of product, service, and ecosystem strategies that connect human insight, business priorities, and technological opportunity into clear, actionable directions. Utilizing strategic frameworks, you will co-create future visions with client leaders; facilitate workshops and collaborative working sessions; and ensure that ideas are translated into practical solutions.
• Lean Product Leadership: Extend strategic design into product definition, helping clients & teams articulate value, weigh effort, and prioritize tradeoffs. You will partner with client & Highland leadership to define long-term roadmaps, key hypotheses, and success measures; shape product scopes, feature sets, and product criteria; and guide decisions so teams stay focused on the most valuable opportunities.
• Research & Insight Integration: Ensure decisions & direction remain grounded in evidence by supporting generative research, and guiding evaluative & secondary research; translating insight into clear business opportunities & strategic recommendations. You will help teams move from discovery to alignment & action, with strong storytelling, presentations, and artifacts that build shared confidence.
• AI-Enabled Design & Production: Use AI-enabled design & production methods to accelerate exploration, prototyping, building, and learning. You will lead teams to rapidly test solution hypotheses, including functional prototypes, collaborate with design engineers & developers, and contribute to the continued evolution of AI-enablement in Highland’s practice.
• Client & Team Leadership: Lead cross-functional teams through complex work with clarity, credibility, and discipline. You will serve as a trusted advisor to client stakeholders, guide teams across research, strategy, design, and product development, lead critical meetings & decision-making sessions, and communicate complex ideas in order to generate alignment and support delivery quality.
• Practice Leadership & Growth: Contribute to the growth of Highland’s design & product practice by strengthening people, points of view, and market presence. You will mentor other designers, share methods & learnings across the team, support business development efforts, and advance Highland’s capabilities in areas such as strategic design leadership, AI-enabled design, and experience-led innovation.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level