Chicago, Illinois, United States · Hybrid
$140k–$155k/yr
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 Chicag…
Skills: Product Strategy, UX Design, Strategic Design, AI-Enabled Design, Product Management
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Lead the creation of product and service strategies while overseeing the end-to-end delivery of complex digital products. This role involves guiding cross-functional teams and utilizing AI-enabled tools to accelerate prototyping and product definition for clients.
Requires 10+ years of experience in product strategy and UX, including at least 6 years in a consulting environment. A Master's degree in Design, HCI, or a related field is preferred along with proficiency in Figma and Miro.
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:
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:
Environment
The Lead Designer & Strategist embodies the Highland Core Values:
Education & Experience Requirements
Compensation & Benefits
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.
Your Partner in Business Process Optimization
Inovus Technologies transforms business operations with expertly custom-configured software solutions. Our seasoned team specializes in business process mapping, consulting, custom-configuration, platform integration, and training for leading platforms like Creatio, monday.com, and SugarCRM. We are dedicated to empowering organizations and their teams to work efficiently and effectively by creating automated, no- code, seamless workflows. Our journey began over 22 years ago with the Highland Group, and in June 2023, we proudly launched Inovus Technologies to better serve our diverse client base with a focused approach. At Inovus, our values—transparency, putting people first, curiosity, and dedication—guide everything we do, ensuring we deliver high-quality solutions that make a meaningful impact.
Offices: 125 S Clark St, Suite 670, Chicago, Illinois 60603, US
Your Partner in Business Process Optimization
Inovus Technologies transforms business operations with expertly custom-configured software solutions. Our seasoned team specializes in business process mapping, consulting, custom-configuration, platform integration, and training for leading platforms like Creatio, monday.com, and SugarCRM. We are dedicated to empowering organizations and their teams to work efficiently and effectively by creating automated, no- code, seamless workflows. Our journey began over 22 years ago with the Highland Group, and in June 2023, we proudly launched Inovus Technologies to better serve our diverse client base with a focused approach. At Inovus, our values—transparency, putting people first, curiosity, and dedication—guide everything we do, ensuring we deliver high-quality solutions that make a meaningful impact.
Offices: 125 S Clark St, Suite 670, Chicago, Illinois 60603, US
