Highland
Lead Design Researcher & Strategist
Chicago, Illinois
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- Seniority
- Lead / management
- Country
- US
- Work mode
- On-site / unstated
- First seen by hirly
- 4 Sept 2026
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Background
Highland is a digital product and innovation consultancy based in Chicago. We research, design, and build digital products and experiences for mission-driven organizations and customer-centric companies. Over 25 years, our team of researchers, strategists, designers, and developers has helped organizations launch over 300 digital products, turning their biggest uncertainties into opportunities for growth.
We often refer to what we design as ‘Experiences that Matter’: digital products and experiences that make the world a better place to live in. We primarily work with leaders of mid-market services companies and enterprise leaders within digital, design, and innovation.
Our mission is rooted in Human Flourishing—inspired by research conducted at Harvard University’s Institute for Quantitative Social Science . We design our work to help human beings flourish, while allowing ourselves to flourish as well. For us, our values—People First, Give a Damn, Be Curious, and Be Transparent—are not just things to hang on the wall, but something we live by every day.
Project Context & Responsibilities
Highland serves clients at every stage in their journey—from early stage, generative research all the way to new product/experience launch. The Lead Design Researcher & Strategist can expect to work across the following realms:
Executing Product/Design Research
Methods Mastery : Demonstrate mastery over a range of Design Research methods and design original research for unique contexts.
Research Execution : Lead the definition, planning, and facilitation of research, using Research Plans, Recruitment, Screeners, Discussion Guides, Deliverables, Reports, etc. as needed for projects.
Synthesis Mastery : Define new methods of synthesizing research to fulfill client goals desirably, feasibly, and viably for design opportunities.
Product-based Research: Adapt exploratory/generative research methods for fast-cycle, product-based research to drive product design and development.
Design Action : Connect the dots from research to ideation, taking responsibility for the team’s translation of insights into ideas, concepts, and value propositions for user co-creation.
Enabling Systemic Action : Capture systemic understanding through frameworks, exposing previously unknown dimensions at play, inspiring new ways for implementation across clients’ limitations & priorities.
Project Leadership : Lead project teams throughout the process, managing timelines, deliverables, & budgets.
Contributing to Design/Product Strategy
Data Analysis : Comfort with data analysis tools like Excel, Google Analytics, Tableau, etc. to analyze and interpret market, user, or product data.
Market Research : Familiarity with market research tools and methods to understand industry/market trends, assemble competitive analyses, identify threats/opportunities.
Business Modeling : Ability to construct preliminary business models for emergent product/service/offerings for viability considerations.
Market Definition : Familiarity with defining initial market size for uncovered opportunities in support of financial modeling and pricing strategies.
GTM and Roadmap planning : Organizing initial go-to-market planning and prioritization of roadmap alongside design development.
Deepening relationships and mentorship
Mentorship: Devote time to guide and support the team/client through the value of Design Thinking as well as product-led approaches.
Strengthening Relationships: Deepen client relationships through an understanding of their organizational context, mission, champions, and barriers.
Networker: Nurturing a growing network of mentors, peers, mentees, and other analogous creatives.
Evolving, framing, and promoting work
Framing New Work: Help frame and plan new projects with potential clients, skilfully advocating for Design Research methods and outcomes in environments new to Design Thinking.
Evolving Methods/Practice: Continuously develop and prototype new research & synthesis methods and processes internally.
Thought-leadership: Leader in the Design Research / Service Design / Design Strategy sphere, contributing across writing, podcasts, teaching, and other channels/media.
Presentation and oration: Sharing reflections & experience with wider audiences through mastery in presentation skills across events, networks, and other professional platforms.
Environment
The Lead Design Researcher & Strategist embodies the Highland Values, People First, Be Curious, Be Open, and Give a Damn. In a Lead Design Researcher & Strategist, we’d love to see:
Self-awareness and knowledge of what you seek in your professional career
An ‘ask for forgiveness rather than permission’ mindset, ability to pivot quickly
Restless desire to learn and ample energy to try new things
Confident interpersonal skills and an impulse to co-create
Ability to think visually and a tendency to forget whose idea it was
Lack of fear to express opinions, question things, and suggest wild ideas
Self-motivation, constantly finding ways to contribute, able to manage ambiguity
Disposed to check-in with others frequently, willing to listen and learn from others
Able to demonstrate genuine concern and thoughtfulness for the well-being of others around you
Discerning and observant, able to connect the dots between seemingly unrelated domains
Time-conscious and organized; able to inspire trust and confidence by meaning what you say
Ability to think big picture, beyond immediate context and issues across work or other work contexts.
Position Requirements:
Preference for an undergraduate degree in design, architecture, anthropology, or humanities, and an MDes, MA, MSc, or MBA. Other comparable training is acceptable.
9+ years of design work experience across diverse contexts/geographies/industries.
At least 7 years of human-centered, exploratory/generative research experience, with a preference for significant experience in consulting, managing clients, teams, & projects.
Strong experience in coaching and mentoring on Design Thinking methods.
Excellent written, visual, and verbal communication skills, with ability to communicate confidently and effectively.
Must be able to converse fluently in English, with a preference for additional languages.
Skill in quantitative research construction and analysis is valued but not required.
Currently have the legal right to work for any employer in the United States.
Hybrid Work Model
The Lead Design Researcher & Strategist role is a high-ranking consulting position with significant client facing responsibilities. Our lead consultants travel, primarily in the US, up to 15% on an annualized basis and attend client and internal events throughout Chicagoland on a regular basis, based on client and internal business needs.
Compensation & Benefits
Full-time annual salary between $132,000 and $142,000 based on experience and qualifications
Annual bonus target based on overall company performance of between $5,000 and $8,000
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)
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Application Guidelines:
Please attach a professional resume.
Please share a PDF or website link of your portfolio giving us a detailed view of your process, team, responsibilities, decisions, and outcomes.
Instead of a cover letter, please build and share a visual framework describing what would make you successful in this role.
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