Lead Designer & Strategist

📍 Job Overview

Job Title: Lead Designer & Strategist

Company: Highland

Location: Chicago, Illinois (Hybrid)

Job Type: Full Time Team Member

Category: Design & Strategy Operations

Date Posted: April 10, 2026

Experience Level: 10+ Years

🚀 Role Summary

• Lead the end-to-end delivery of complex digital product and service engagements, blending strategic design, product management principles, and AI-enabled workflows.

• Drive the creation of innovative product, service, and ecosystem strategies that align human insights, business objectives, and technological opportunities.

• Act as a consultative, client-facing leader, partnering with principals and cross-functional teams to translate strategy into actionable product roadmaps and tangible outcomes.

• Leverage AI-assisted tools and methodologies to accelerate research, exploration, prototyping, and development cycles, enhancing team efficiency and speed to market.

• Foster a culture of continuous learning and practice growth within Highland's design and product teams, mentoring others and contributing to business development efforts.

📝 Enhancement Note: This role is positioned as a senior contributor within a digital product and innovation consultancy. While not a traditional "operations" role in the sense of Sales Ops or Rev Ops, the strategic leadership, process definition, client engagement management, and cross-functional team guidance all fall under the broader umbrella of GTM (Go-To-Market) and service delivery operations. The emphasis on AI-enabled workflows and accelerating delivery cycles highlights a focus on operational efficiency within the design and development process.

📈 Primary Responsibilities

• Strategic Design Leadership: Lead the development of product, service, and ecosystem strategies by synthesizing human insights, business priorities, and technological potential into clear, actionable plans. Facilitate workshops and collaborative sessions with clients to co-create future visions and translate them into practical solutions.

• Lean Product Leadership: Define product value, prioritize efforts, and manage trade-offs by integrating strategic design with product management practices. Partner with leadership to establish long-term roadmaps, key hypotheses, and success metrics, guiding teams to focus on high-value opportunities.

• Research & Insight Integration: Champion data-informed decision-making by supporting generative, evaluative, and secondary research. Translate research insights into compelling business opportunities and strategic recommendations through strong storytelling and clear artifacts that build confidence.

• AI-Enabled Design & Production: Utilize generative AI and other AI-enabled tools to accelerate design exploration, rapid prototyping, and learning cycles. Collaborate with design engineers and developers to test solution hypotheses and contribute to the evolution of AI enablement within the practice.

• Client & Team Leadership: Guide multidisciplinary teams (research, strategy, design, engineering) through complex projects with clarity and credibility. Serve as a trusted advisor to client stakeholders, lead critical meetings, and effectively communicate complex ideas to ensure alignment and high-quality delivery.

• Practice Leadership & Growth: Contribute to the advancement of Highland's design and product practice by mentoring designers, sharing methods and learnings, supporting business development initiatives, and enhancing capabilities in strategic design, AI-enabled design, and experience-led innovation.

📝 Enhancement Note: The core responsibilities clearly indicate a senior role focused on project leadership, client management, and strategic output. The integration of "AI-enabled design & production" and "lean product leadership" points to a strong emphasis on efficient, outcome-oriented project execution, which is a key aspect of operational excellence in a consultancy setting.

🎓 Skills & Qualifications

Education: Master's degree or equivalent experience in Design, Human-Computer Interaction (HCI), or a related field.

Experience: 10+ years of progressive experience in product strategy, User Experience (UX) design, and strategic design. Proven experience leading multidisciplinary teams and complex client engagements from inception to completion.

Required Skills:

• Strategic Design & Product Strategy: Demonstrated ability to conceptualize and articulate high-level strategies for digital products, services, and ecosystems.

• UX Design Expertise: Deep understanding and practical application of UX principles, research methodologies, and design best practices.

• Product Management Acumen: Familiarity with product discovery, definition, roadmap creation, and prioritization frameworks.

• Cross-Functional Leadership: Proven experience leading and motivating diverse teams, fostering collaboration, and driving consensus.

• Client Engagement & Facilitation: Exceptional skills in client communication, workshop facilitation, and building trusted advisor relationships.

• Storytelling & Communication: Ability to articulate complex ideas concisely and persuasively to various stakeholders.

• Modern Design Tools: Proficiency with collaborative design platforms such as Miro and Figma.

• AI-Enabled Workflows: Experience or strong aptitude for integrating AI tools into design and production processes.

Preferred Skills:

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

• Familiarity with generative AI tools for ideation, prototyping, and content creation.

• Experience in digital product and innovation consultancy environments.

• Demonstrated ability to contribute to business development and client acquisition efforts.

📝 Enhancement Note: The requirements emphasize a blend of strategic thinking, design execution, and leadership. The explicit mention of AI-enabled workflows and tools like Miro and Figma signals a modern, agile approach to project delivery, which is critical for operational efficiency in a consultancy. The "10+ years" and Master's degree requirement indicate a senior, highly experienced candidate.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Case Studies of End-to-End Engagements: Demonstrate leadership in complex projects from initial research and strategy through product definition and delivery. Showcase your ability to connect human insight with business goals.

• Strategic Frameworks & Deliverables: Include examples of strategic frameworks, roadmaps, and product visions you've developed. Highlight how these artifacts guided decision-making and aligned teams.

• AI Integration Examples: Showcase projects where AI-enabled tools were used to accelerate exploration, prototyping, or learning. Detail the impact on efficiency and outcomes.

• Collaboration & Facilitation Evidence: Provide examples of how you've led workshops, facilitated client sessions, and managed cross-functional teams to achieve alignment and drive progress.

• Problem-Solving & Impact: Detail specific challenges faced on projects and how your strategic and design leadership led to measurable business outcomes or improved user experiences.

Process Documentation:

• Workshop Design & Facilitation: Document your approach to designing and leading client and team workshops, including agenda setting, activity design, and outcome anchoring.

• Strategic Planning Methodologies: Outline the methodologies you employ for strategic planning, product discovery, and roadmap development, emphasizing how you integrate research and business needs.

• AI-Enhanced Workflow Implementation: Describe how you've implemented or would implement AI tools within design and production processes to improve efficiency, accelerate iteration, and enhance output quality.

• Cross-Functional Team Management: Detail your strategies for leading and coordinating diverse teams, ensuring clear communication, alignment, and effective delivery.

📝 Enhancement Note: For a role focused on strategic design and product leadership within a consultancy, a portfolio is crucial. It needs to demonstrate not just design output, but the strategic thinking, process leadership, and client management capabilities required to drive complex projects. The emphasis on AI integration and efficiency is a key differentiator.

💵 Compensation & Benefits

Salary Range: $135,000 - $150,000 per year

Benefits:

• Full-time team member benefits package (details not specified, but typically includes health, dental, vision insurance).

• Opportunities for professional development and continuous learning.

• Contribution to a dynamic and innovative work environment focused on mission-driven organizations.

• Hybrid work model offering flexibility between office, client sites, and remote work.

• Opportunity to work on impactful digital products and services that improve people's lives.

Working Hours: 40 hours per week, with flexibility inherent in a hybrid work model.

📝 Enhancement Note: The salary range provided is competitive for a senior-level design and strategy role in a major metropolitan area like Chicago. Benefits are not detailed but are expected to align with full-time employment in a professional services firm. The hybrid nature of the role offers operational flexibility for the employee.

🎯 Team & Company Context

🏢 Company Culture

Industry: Digital Product & Innovation Consultancy. Highland partners with mid-market services organizations, membership-based institutions, and enterprise innovation teams to design and launch digital products that matter.

Company Size: Not explicitly stated, but the description implies a lean, focused team structure, suggesting a medium-sized consultancy.

Founded: Over 25 years ago, indicating a stable, experienced firm with a long-standing reputation.

Team Structure:

• Lean, focused, and multidisciplinary teams comprising researchers, strategists, designers, and engineers.

• Collaborative environment where practitioners partner closely to deliver end-to-end solutions.

Methodology:

• Human-Centered & Research-Grounded: Work is grounded in Human Flourishing principles, inspired by research from Harvard University.

• AI-Accelerated: Increasingly utilizes generative AI to enhance team efficiency, accelerate learning, and broaden access to their offerings.

• Agile & Iterative: Focus on iterative development, rapid testing of hypotheses, and delivering working software.

• Strategic & Outcome-Oriented: Emphasis on connecting human insight with business priorities and technological opportunity to achieve measurable outcomes.

Company Website: inovustech.io (derived from domain_derived)

📝 Enhancement Note: Highland positions itself as a thoughtful, values-driven consultancy that leverages modern methodologies, including AI, to deliver impactful digital products. The company culture emphasizes collaboration, continuous learning, and a commitment to client success and human well-being. The "25+ years" of experience suggests a mature, established, yet forward-thinking organization.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position within the design and strategy practice. It is a "Lead" role, signifying responsibility for project direction, team mentorship, and contributing to the firm's strategic growth. It sits above individual contributor designers and strategists and likely reports to a Principal or Director.

Reporting Structure: The Lead Designer & Strategist will partner closely with a "client principal" and collaborate with research, design, engineering, and strategy teammates. This indicates a matrixed reporting structure common in consultancies, with both project-specific leadership and functional reporting lines.

Operations Impact: The role directly impacts the operational success of client engagements by ensuring strategic alignment, efficient delivery, and high-quality outcomes. By leveraging AI and lean principles, the role contributes to the consultancy's ability to deliver more value, faster, and potentially at a more competitive cost, thereby enhancing its market position and revenue generation.

Growth Opportunities:

• Leadership Advancement: Potential to grow into Principal or Director roles within the consultancy, taking on larger client portfolios and broader practice leadership responsibilities.

• Specialization & Expertise: Deepen expertise in AI-enabled design, strategic product innovation, or specific industry verticals.

• Mentorship & Practice Development: Contribute significantly to shaping Highland's methodologies, training junior staff, and building the firm's reputation and capabilities.

• Client Relationship Management: Develop long-term strategic partnerships with key clients, becoming a trusted advisor.

📝 Enhancement Note: The career path for this role is clearly within the consultancy's leadership track. The emphasis on practice development and business development suggests opportunities for individuals with entrepreneurial drive and a desire to shape the future of the firm's offerings.

🌐 Work Environment

Office Type: Hybrid work environment, combining in-office collaboration at Highland's Chicago offices, client site visits, and remote work. This offers a blend of structured team interaction and individual flexibility.

Office Location(s): Chicago, Illinois. Specific client office locations will vary based on project needs.

Workspace Context:

• Collaborative Hub: Highland's Chicago office serves as a hub for team collaboration, client meetings, and fostering company culture.

• Technology-Enabled: Expect access to modern design tools (Miro, Figma) and potentially AI-powered platforms to support work.

• Dynamic Project Teams: Work within project-specific teams, fostering close collaboration with diverse specialists on each engagement.

• Client-Facing Interaction: Significant interaction with client stakeholders, requiring adaptability to different professional environments.

Work Schedule: Standard 40-hour work week, with the expectation of flexibility to meet client needs and project deadlines. The hybrid model allows for personal management of work location and time within these parameters.

📝 Enhancement Note: The hybrid model is a key feature, offering operational flexibility. Candidates should be comfortable working autonomously and collaboratively, both in-person and remotely, and be prepared for client-site engagements.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess experience, skills, and alignment with the role's requirements.

• Portfolio Presentation & Discussion: Candidates will likely present key case studies from their portfolio, detailing their strategic approach, leadership, and impact on project outcomes. Expect detailed questions about their process, decision-making, and use of tools, including AI.

• Client-Facing Scenario / Case Study: A potential exercise or discussion simulating a client engagement, assessing strategic thinking, problem-solving, and communication skills. This might involve analyzing a business problem and proposing a strategic approach.

• Team & Culture Fit Interviews: Discussions with Highland principals and team members to evaluate cultural alignment with Highland's values (People First, Be Curious, Be Transparent, Give a Damn) and collaborative style.

• Final Interview: Discussion with senior leadership to confirm fit and discuss terms of employment.

Portfolio Review Tips:

• Focus on Impact: Clearly articulate the business impact and user value delivered by your projects. Quantify results wherever possible (e.g., increased engagement, reduced time-to-market, improved conversion rates).

• Showcase Strategic Thinking: Go beyond visual design; demonstrate how you identified problems, developed strategies, and guided teams toward solutions.

• Highlight Leadership: Provide examples of how you led multidisciplinary teams, facilitated complex discussions, and managed client relationships.

• Demonstrate AI Integration: If applicable, clearly explain how AI tools were used, the specific benefits achieved, and your role in implementing them.

• Structure for Clarity: Organize your portfolio with clear case studies, outlining the challenge, your role, the process, the solution, and the results.

Challenge Preparation:

• Understand Highland's Methodology: Familiarize yourself with their values, approach to Human Flourishing, and use of AI.

• Prepare Strategic Scenarios: Be ready to discuss how you would approach common design strategy challenges (e.g., defining a new digital product, pivoting a failing product, integrating AI into an existing service).

• Articulate Your Values: Be prepared to discuss how your personal values align with Highland's core values.

• Practice Your Storytelling: Develop compelling narratives for your portfolio case studies that clearly communicate your strategic contribution and leadership.

📝 Enhancement Note: The interview process is designed to assess strategic capability, leadership, client management, and cultural fit. A strong portfolio that demonstrates end-to-end project leadership and strategic thinking, with specific attention to AI integration and impact, will be critical.

🛠 Tools & Technology Stack

Primary Tools:

• Miro: Essential for collaborative ideation, workshop facilitation, journey mapping, and strategic planning.

• Figma: Core tool for UI/UX design, prototyping, and design system development.

• AI-Enabled Design & Production Tools: This is a broad category, but candidates should be prepared to discuss their experience with AI tools for:

  • Generative Design Exploration: Tools for rapid ideation and concept generation.
  • Content Creation: AI for text generation, image creation, or data synthesis.
  • Prototyping Acceleration: AI tools that can speed up the creation of interactive prototypes.
  • Research Synthesis: AI for analyzing qualitative and quantitative data.

Analytics & Reporting: While not explicitly mentioned as a primary tool for this role, familiarity with analytics platforms (e.g., Google Analytics, Mixpanel, Amplitude) and data visualization tools (e.g., Tableau, Power BI) would be beneficial for grounding strategic recommendations in data.

CRM & Automation: Experience with CRM systems (e.g., Salesforce, HubSpot) and project management/collaboration tools (e.g., Asana, Jira, Notion) is common in consultancy environments and can be beneficial for understanding client contexts and managing internal workflows.

📝 Enhancement Note: Proficiency in Miro and Figma is explicitly required. The emphasis on AI-enabled tools suggests a need for candidates who are not only aware of AI but actively integrating it into their design and strategy workflows to drive efficiency and innovation.

👥 Team Culture & Values

Operations Values (Highland's Core Values):

• People First: Prioritize making a positive impact on individuals' lives, including employees, clients, and end-users. This translates to empathetic design and considerate collaboration.

• Be Curious: Foster a continuous learning environment where understanding the big picture and seeking new knowledge is encouraged and shared. This drives innovation and deeper insights.

• Be Transparent: Promote open communication, accountability, and problem-solving without blame. This builds trust internally and with clients.

• Give a Damn: Demonstrate a deep commitment to client goals and delivering high-quality work that is a source of pride. This ensures dedication and excellence in execution.

Collaboration Style:

• Cross-Functional Integration: Seamless collaboration across research, strategy, design, and engineering disciplines is fundamental.

• Client Partnership: A consultative and collaborative approach with clients, acting as a trusted advisor and co-creator.

• Mentorship & Knowledge Sharing: An environment where experienced practitioners actively mentor others and share learnings to elevate the entire team's capabilities.

• Agile & Iterative: Embracing iterative processes, feedback loops, and adaptability to achieve optimal outcomes.

📝 Enhancement Note: The company's values are central to its identity and operational approach. Candidates who can demonstrate alignment with these values, particularly "Be Curious" and "Give a Damn," will likely be strong fits, as they directly relate to the drive for innovation and quality service delivery.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Client Ambiguity: Helping clients, who may have varying levels of digital maturity, define clear strategies and product visions from ambiguous starting points.

• Integrating AI Effectively: Successfully adopting and scaling AI tools within design and production workflows while ensuring quality, ethical considerations, and demonstrable ROI.

• Balancing Strategy with Execution: Ensuring that strategic vision translates into practical, implementable product solutions that meet both user needs and business objectives.

• Leading Diverse Stakeholders: Managing expectations and driving alignment among various client stakeholders and internal team members with potentially competing priorities.

• Continuous Skill Evolution: Staying ahead of rapid advancements in design technology, AI, and product development methodologies.

Learning & Development Opportunities:

• Advanced AI in Design: Opportunities to explore and master cutting-edge AI tools and techniques for design and product development.

• Strategic Leadership Development: Formal and informal training in client principalship, business development, and practice leadership.

• Industry Conferences & Workshops: Participation in events focused on design, innovation, AI, and product management.

• Mentorship Program: Access to senior leaders for guidance on career progression, skill development, and navigating complex challenges.

• Exposure to Diverse Industries: Working with a wide range of clients allows for broad learning across different sectors and business models.

📝 Enhancement Note: The challenges highlight the dynamic nature of consultancy work and the forefront of technological adoption. Growth opportunities are substantial, focusing on leadership, specialized expertise, and continuous professional development within a supportive environment.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led a complex digital product strategy initiative from conception to definition. What were the key challenges, and how did you overcome them?" (Focus on your strategic framework, decision-making process, and leadership.)

• "How would you approach defining a product roadmap for a client facing significant market disruption?" (Assess your ability to integrate research, business goals, and future vision.)

• "Walk us through a project where you leveraged AI-enabled tools to accelerate design exploration or prototyping. What was the impact?" (Demonstrate your practical experience with AI and its benefits.)

Company & Culture Questions:

• "How do Highland's core values (People First, Be Curious, Be Transparent, Give a Damn) resonate with your own professional philosophy?" (Be prepared to provide specific examples of how you embody these values.)

• "Describe your ideal collaborative environment. How do you foster strong relationships with cross-functional teams and client stakeholders?" (Highlight your teamwork and client management skills.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly articulate the client's challenge, your role and responsibilities, the strategic approach you took, the solutions developed, and the measurable outcomes achieved.

• Emphasize Your Leadership: Highlight instances where you led teams, facilitated critical discussions, managed client relationships, and drove decision-making.

• Showcase Process & Tools: Explain your design process, including how you integrated research and utilized tools like Miro and Figma. If AI was involved, detail its application and impact.

• Quantify Impact: Whenever possible, present data and metrics that demonstrate the success of your projects (e.g., user engagement, conversion rates, time-to-market reduction).

• Be Ready for Deep Dives: Anticipate detailed questions about your decisions, methodologies, and problem-solving approaches.

📝 Enhancement Note: Preparation should focus on articulating strategic thinking, leadership capabilities, and a practical understanding of modern design/product methodologies, including AI. Demonstrating alignment with Highland's values is also paramount.

📌 Application Steps

To apply for this Lead Designer & Strategist position:

• Submit your application through the provided link on Highland's BambooHR careers page.

• Customize Your Resume: Tailor your resume to highlight your 10+ years of experience in product strategy, UX, and strategic design, emphasizing leadership roles and client engagement successes. Incorporate keywords from the job description such as "AI-enabled design," "product roadmaps," and "cross-functional leadership."

• Curate Your Portfolio: Select 2-3 key projects that best showcase your end-to-end strategic leadership, AI integration experience (if applicable), and ability to drive tangible business outcomes. Ensure your portfolio clearly details the challenge, your strategic approach, your leadership role, and the results achieved.

• Prepare Your Narrative: Practice articulating your portfolio case studies with confidence, focusing on your strategic decision-making, leadership impact, and how you leverage modern tools and methodologies. Be ready to discuss how you embody Highland's core values.

• Research Highland: Familiarize yourself with Highland's website (inovustech.io), their approach to "Human Flourishing," their client work, and their core values to demonstrate genuine interest and cultural alignment.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.