Lead Designer & Strategist

Job Description

Job Title: Lead Designer & Strategist
Work Location: Hybrid at our offices in Chicago, at our client’s offices, and remote

Background

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 often refer to what we design as Experiences that Matter: digital products & services that measurably 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 clear 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.

Role Overview

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, highly 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.

This role 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.

Core Responsibilities

1. 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

Succeeding with Highland

What Success Looks Like
Within 3-4 months, a successful Lead Designer & Strategist will:

• Lead complex client engagements from discovery through product definition.
• Help clients translate strategy into clear product roadmaps and experience directions.
• Elevate the quality of strategic design thinking across Highland projects.
• Use AI-enabled tools and prototyping methods to accelerate learning and delivery.
• Become a trusted partner to Highland principals and client leadership teams.

Environment 

The Lead Designer & Strategist embodies the Highland Core Values:

• People First: What we make and how we work should make it a little bit better to be alive: for us, our clients, and their customers.
• Be Curious: The big picture is everyone's responsibility. There is always more to learn. We are generous in teaching what we know.
• Be Transparent: We respond to problems with solutions, not blame. Vulnerability, while risky, leads to trust and understanding. We're accountable to our clients and to each other. Even when things aren't going well.
• Give a Damn: Our client's goals are our goals. We do work we can be proud of. Quality is non-negotiable.

Education & Experience Requirements

• 10+ years of experience in product strategy, UX, & strategic design
  • Including 6+ years in a consulting environment (outside of an in-house role)
• Proven experience leading multidisciplinary teams and client engagements
• Strong experience translating opportunities into product & service strategies
• Experience with product discovery, definition, roadmaps, and criteria
• 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

Compensation & Benefits

• Full-time annual salary between $140,000 and $155,000 based on experience and qualifications
• Annual bonus target based on overall company performance of between $6,000 and $10,000
• Health, dental and vision insurance
• 401k retirement savings plan
• Unlimited sick time, 9 paid company holidays, 4 weeks paid time off
• 40 hours of professional development time and a $1,000 learning stipend each year
• Fully paid parental leave: 12 weeks for birth mothers or 6 weeks for non-birth parents
• Short-term and long-term disability insurance and life insurance (Highland pays 100% of the premiums)

Our Commitment to Diversity and Inclusion

Highland is committed to creating a just, equitable workplace, and is actively seeking candidates who can bring the value of diverse lived experiences to this position.  We look for candidates who have a high level of demonstrated comfort with cultural competency; women, people of color, people with disabilities, and people who identify as LGBTQ are encouraged to apply.