Lead Designer & Strategist

📍 Job Overview

Job Title: Lead Designer & Strategist

Company: Highland

Location: Chicago, Illinois, United States

Job Type: Full Time Team Member

Category: Product Design & Strategy Operations

Date Posted: 2026-04-10

Experience Level: Senior (10+ years)

Remote Status: Hybrid

🚀 Role Summary

• Spearhead the strategic design and product strategy for complex, client-facing digital product innovation projects, leveraging AI-enabled tools to accelerate discovery and delivery.

• Lead end-to-end project execution, from initial strategy formulation and product definition to roadmap development and the delivery of working software, ensuring alignment with client business objectives and human insight.

• Drive the integration of research and insights into actionable product strategies, utilizing strong facilitation and storytelling skills to build confidence and guide decision-making across cross-functional teams.

• Contribute to the growth and evolution of Highland's design and product practice through mentorship, knowledge sharing, and advancing capabilities in AI-enabled production and experience-led innovation.

📝 Enhancement Note: This role is positioned within a digital product and innovation consultancy, indicating a focus on client-facing engagements and project-based work. The "Lead Designer & Strategist" title, combined with "10+ years of experience" and responsibilities spanning "product strategy, UX, & strategic design," suggests a senior individual contributor role with significant autonomy and leadership expectations. The emphasis on AI-enabled design and production highlights a forward-thinking approach to service delivery. This role sits at the intersection of design, strategy, and product management, requiring a blend of creative problem-solving and business acumen.

📈 Primary Responsibilities

• Lead the conception and development of comprehensive product, service, and ecosystem strategies, translating human insights, business priorities, and technological opportunities into actionable plans.

• Facilitate strategic workshops, collaborative working sessions, and client visioning exercises to co-create future states and ensure strategic alignment.

• Drive product definition by articulating value propositions, prioritizing trade-offs, and defining key hypotheses and success measures for product roadmaps and feature sets.

• Champion the integration of generative, evaluative, and secondary research findings into strategic recommendations and clear business opportunities, supported by compelling presentations and artifacts.

• Leverage AI-enabled design and production methodologies to expedite exploration, prototyping, development, and learning cycles, fostering rapid hypothesis testing and iteration.

• Guide cross-functional teams (research, design, engineering, strategy) through complex project phases, ensuring clarity, credibility, and adherence to delivery quality standards.

• Act as a trusted advisor to client stakeholders, managing relationships and communicating complex ideas effectively to secure alignment and drive project success.

• Mentor junior designers and contribute to the continuous improvement of Highland's design and product practice through thought leadership and knowledge sharing.

• Support business development initiatives by contributing expertise and insights to proposals and client presentations.

• Actively participate in the evolution of AI-enablement within Highland's service offerings and operational workflows.

📝 Enhancement Note: The responsibilities emphasize a holistic approach to product development, starting from high-level strategy and extending through execution and team leadership. The explicit mention of "AI-enabled design & production" and "AI-enabled design & production workflows" indicates a strong expectation for candidates to be proficient with or eager to adopt AI tools in their design and strategy processes, which is a key differentiator for this role.

🎓 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.

Required Skills:

• Demonstrated expertise in leading multidisciplinary teams and managing complex client engagements from inception to completion.

• Proven ability to translate strategic opportunities into well-defined product and service strategies, with a strong understanding of business objectives.

• Extensive experience in product discovery, definition, roadmap creation, and prioritization frameworks.

• Proficiency with modern, collaborative design and strategy tools, specifically Miro and Figma, for workshop facilitation and artifact creation.

• Exceptional communication, facilitation, and storytelling skills, with the ability to articulate complex ideas clearly to diverse audiences.

• A consultative mindset, capable of acting as a trusted advisor to clients and internal stakeholders.

• Generalist mindset with the ability to integrate product management principles into design practice.

Preferred Skills:

• Experience with AI-enabled design and production workflows, including practical application in accelerating exploration, prototyping, and learning.

• Experience in digital product innovation consultancy or a similar client-service environment.

• Familiarity with agile development methodologies and their integration with design and strategy processes.

• Experience with generative AI tools for ideation, content creation, or workflow automation.

• Knowledge of quantitative social science research principles as applied to product development.

📝 Enhancement Note: The emphasis on "10+ years of experience" and a "Masters degree or equivalent experience" firmly places this role at a senior level. The requirement for "Miro & Figma" is specific and actionable, while "AI-enabled design & production workflows" is a key differentiator that candidates should highlight if they have relevant experience. The "generalist mindset" suggests a need for adaptability and a broad understanding of the product lifecycle.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least two significant client engagements where you led strategic design and product strategy from discovery through product definition.

• Include case studies demonstrating your ability to translate complex human insights and business needs into clear product roadmaps and actionable experience directions.

• Present examples of how you have utilized AI-enabled tools or methodologies to accelerate learning, prototyping, or delivery cycles in past projects.

• Provide evidence of your facilitation skills through documented workshop outcomes, strategic frameworks used, or collaborative artifacts produced.

Process Documentation:

• Clearly articulate your approach to integrating research findings (generative, evaluative, secondary) into strategic recommendations and product decisions, illustrating the transition from discovery to alignment.

• Demonstrate your methodology for leading cross-functional teams through complex work, highlighting how you ensure clarity, credibility, and quality in delivery.

• Outline your process for mentoring other designers and contributing to the growth of a design and product practice, including knowledge sharing and point-of-view development.

• Showcase your experience in client leadership, including how you build trust, manage expectations, and communicate complex ideas to gain stakeholder buy-in.

📝 Enhancement Note: For a role focused on strategy and leadership, the portfolio should emphasize strategic thinking, client impact, and process leadership. Including examples of AI integration is crucial. The emphasis on "process documentation" within the portfolio means candidates should be prepared to articulate their methodologies and how they drive efficiency and quality in their work.

💵 Compensation & Benefits

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

Benefits:

• Comprehensive health, dental, and vision insurance plans.

• Generous paid time off (PTO) policy, including vacation, sick days, and holidays.

• Retirement savings plan with company matching contributions.

• Professional development stipend for conferences, training, and certifications relevant to design, strategy, and AI.

• Opportunities for remote work flexibility within a hybrid model, complementing in-office collaboration.

• Supportive work environment that fosters continuous learning and professional growth.

Working Hours: Standard 40-hour work week, with flexibility expected based on client project needs and deadlines.

📝 Enhancement Note: The provided salary range of $135,000 - $150,000 USD aligns with senior-level design and strategy roles in a major metropolitan area like Chicago, especially within a consultancy setting. The benefits package is standard for a full-time role, with specific mention of professional development and hybrid flexibility being key attractors for this type of position.

🎯 Team & Company Context

🏢 Company Culture

Industry: Digital Product & Innovation Consultancy. Highland operates within the technology services sector, specializing in helping organizations design and launch impactful digital products and services.

Company Size: While not explicitly stated, "lean, focused teams" and a consultancy model suggest a mid-sized firm, likely ranging from 50-200 employees, enabling agile operations and close-knit team dynamics.

Founded: Over 25 years ago, indicating a mature, established firm with a deep history of client partnerships and market experience.

Team Structure:

• Teams are described as "lean, focused" and assembled for specific projects, implying a matrixed or project-based organizational structure rather than rigid departmental silos.

• Project teams likely include researchers, strategists, designers, and engineers, fostering a multidisciplinary collaborative environment.

Methodology:

• Grounded in Human Flourishing principles, drawing inspiration from Harvard University research, indicating a human-centered approach to design and strategy.

• Employs AI to accelerate exploration, prototyping, and learning, integrating cutting-edge technology into their service delivery.

• Focuses on creating "Experiences that Matter," emphasizing the impact and value of digital products for both users and organizations.

• Utilizes a combination of research, strategy, design, and engineering to deliver end-to-end solutions.

Company Website: https://highland.bamboohr.com/careers

📝 Enhancement Note: Highland's positioning as an "innovation consultancy" with a 25+ year history suggests a stable yet forward-thinking company. The emphasis on "Human Flourishing" and "Experiences that Matter" points to a mission-driven culture with a focus on impactful work. The integration of AI is presented as a core part of their modern approach.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior leadership position within the design and strategy practice. It is a critical individual contributor role focused on leading complex projects, mentoring others, and contributing to practice development, rather than direct people management.

Reporting Structure: The Lead Designer & Strategist will work closely with Highland principals and client principals, indicating a collaborative reporting structure that emphasizes client partnership and internal mentorship.

Operations Impact: The role has a direct and significant impact on client success by shaping product strategy, driving innovation, and ensuring the delivery of high-quality digital products. It influences both client business outcomes and Highland's service offerings and market reputation.

Growth Opportunities:

• Specialization: Deepen expertise in AI-enabled design, strategic product leadership, or specific industry verticals served by Highland.

• Leadership: Progress towards Principal Designer/Strategist roles, taking on larger client portfolios, business development responsibilities, and strategic practice leadership.

• Mentorship: Formalize mentorship of junior team members, contributing to their career development and building a stronger internal talent pipeline.

• Thought Leadership: Contribute to Highland's intellectual property, industry presence, and go-to-market strategies through speaking engagements, publications, and development of new service offerings.

📝 Enhancement Note: The growth path for a Lead Designer & Strategist at a consultancy typically involves moving towards more strategic client leadership, business development, and practice management responsibilities, often culminating in a Principal or Partner-level role. The emphasis on "practice leadership" suggests active involvement in shaping the company's future offerings.

🌐 Work Environment

Office Type: Hybrid work model. This involves a blend of working from Highland's Chicago offices, client sites, and remotely.

Office Location(s): Chicago, Illinois, with client office engagements also specified. The physical office location in Chicago (ZIP code 60603) is in a central business district, likely offering good accessibility and proximity to other professional services firms.

Workspace Context:

• Collaborative Environment: Expect a dynamic and collaborative setting, with regular in-person and virtual sessions for team strategy, client workshops, and ideation. The hybrid nature requires strong self-management and communication skills.

• Tools & Technology: Access to industry-standard design and strategy tools like Miro and Figma, with an emphasis on leveraging AI-enabled technologies to enhance productivity and innovation.

• Client Interaction: Significant portion of time will be spent interacting with clients, both on-site and remotely, requiring adaptability to various client environments and cultures.

Work Schedule: A standard 40-hour work week is the baseline, but the nature of consulting and client-facing roles often necessitates flexibility. Be prepared for periods of higher intensity to meet project deadlines or client needs, balanced by the flexibility offered by the hybrid model.

📝 Enhancement Note: The hybrid nature of this role is a key aspect, requiring candidates to be comfortable with a mix of in-person and remote collaboration. The mention of client site visits highlights the client-facing aspect of the consultancy model.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application and portfolio to assess alignment with the role's requirements.

• Hiring Manager/Principal Interview: Discussion focused on your strategic design and product leadership experience, client management skills, and approach to complex problem-solving. Expect questions about your experience with AI in design.

• Case Study Presentation/Workshop: You may be asked to present a past project or participate in a simulated client workshop to demonstrate your strategic thinking, facilitation skills, and ability to translate insights into actionable plans. This is a critical opportunity to showcase your portfolio.

• Team Interviews: Meetings with potential teammates (designers, strategists, engineers) to assess cultural fit, collaboration style, and technical capabilities.

• Final Interview: Typically with a senior leader or partner to discuss overall fit, career aspirations, and confirm alignment with Highland's values and business goals.

Portfolio Review Tips:

• Curate Strategically: Select 2-3 of your most impactful projects that best represent your leadership in strategic design, product strategy, and AI-enabled production.

• Tell a Story: For each project, clearly articulate the client's challenge, your role and approach, the strategic thinking involved, the methodologies used (including AI), the outcomes achieved, and your key learnings. Quantify impact wherever possible.

• Highlight AI Integration: Explicitly demonstrate how you've used AI tools to accelerate processes, generate insights, or enhance deliverables. This is a key differentiator for this role.

• Showcase Facilitation: Include examples of how you've led workshops, facilitated discussions, or created artifacts that drove alignment and decision-making.

• Be Prepared to Discuss: Be ready to dive deep into the strategic rationale, trade-offs considered, and the "why" behind your decisions for each project presented.

Challenge Preparation:

• Strategic Frameworks: Familiarize yourself with common strategic design frameworks (e.g., Design Thinking, Lean UX, Jobs-to-be-Done) and how to apply them in a consultancy context.

• AI in Design: Be prepared to discuss current trends and your practical experience with AI tools for ideation, prototyping, research analysis, and content generation in design and strategy.

• Client Scenarios: Think through how you would approach common client challenges, such as defining a new digital product, optimizing an existing service, or navigating market uncertainty.

• Communication: Practice articulating complex strategies and design decisions concisely and persuasively, anticipating stakeholder questions and concerns.

📝 Enhancement Note: The interview process emphasizes practical application of skills, strategic thinking, and client-facing capabilities. The portfolio review is a critical component, and candidates should tailor their presentations to highlight experience with AI and strategic leadership.

🛠 Tools & Technology Stack

Primary Tools:

• Miro: Essential for collaborative ideation, workshop facilitation, journey mapping, and strategic planning. Proficiency in creating structured and visually engaging Miro boards is expected.

• Figma: The primary tool for interface design, prototyping, and design system management. Experience with advanced features, collaboration, and potentially design systems is valued.

• AI-Enabled Design Tools: This is a broad category, but candidates should be prepared to discuss their experience with AI tools for ideation (e.g., ChatGPT, Midjourney for concept generation), research synthesis, content creation, and potentially code generation or prototyping acceleration.

Analytics & Reporting:

CRM & Automation:

• Experience with CRM systems (e.g., Salesforce, HubSpot) is generally valuable in understanding client business contexts, although not a direct requirement for this design/strategy role. Familiarity with project management and collaboration tools (e.g., Jira, Asana, Slack) is also expected for team coordination.

📝 Enhancement Note: The explicit mention of Miro and Figma points to the core design and collaboration tools. The "AI-enabled design & production workflows" is a key indicator that candidates should be ready to discuss their proficiency with AI tools relevant to the design and strategy process, rather than just general AI knowledge.

👥 Team Culture & Values

Operations Values:

• People First: A commitment to creating positive experiences for clients, their customers, and internal team members. This translates to empathetic design and considerate collaboration.

• Be Curious: A drive for continuous learning, exploration, and understanding the "big picture." This encourages asking questions, seeking new knowledge, and sharing insights openly.

• Be Transparent: A culture of accountability, honesty, and solution-oriented problem-solving. This means addressing challenges directly, offering solutions, and fostering trust.

• Give a Damn: A dedication to client success, quality of work, and doing work that is meaningful and impactful. This emphasizes ownership and a commitment to excellence.

Collaboration Style:

• Cross-functional Integration: Highland emphasizes assembling "lean, focused teams" with researchers, strategists, designers, and engineers, indicating a highly integrated, collaborative approach where different disciplines work closely together.

• Client Partnership: A strong emphasis on building trusted advisor relationships with clients, involving them actively in the strategic and design process.

• Knowledge Sharing: The value "Be Curious" implies a culture where sharing methods, learnings, and best practices across the team is encouraged and expected.

📝 Enhancement Note: The company's core values are clearly articulated and are central to their culture. Candidates should be prepared to demonstrate how they embody these values in their work and interactions, particularly "People First" and "Give a Damn" in client-facing roles, and "Be Curious" and "Be Transparent" in team collaborations and problem-solving.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Client Ambiguity: Clients often come with complex, ill-defined problems. A key challenge will be to bring clarity through strategic design and research, guiding them towards actionable solutions.

• Integrating AI Effectively: Moving beyond theoretical AI applications to practical, impactful integration into client projects requires continuous learning, experimentation, and demonstrating tangible value.

• Balancing Strategy & Execution: The role requires bridging the gap between high-level strategy and the practicalities of product development, ensuring strategic vision translates into tangible, high-quality deliverables.

• Managing Diverse Stakeholders: Effectively aligning and communicating with a range of client stakeholders and internal team members with different perspectives and priorities.

Learning & Development Opportunities:

• AI Advancement: Opportunities to become an expert in leveraging emerging AI tools and methodologies for design and strategy, potentially shaping Highland's future service offerings.

• Strategic Leadership: Deepen expertise in complex product strategy, service design, and ecosystem thinking, leading to more significant client engagements and higher-level strategic influence.

• Mentorship Programs: Formal and informal opportunities to mentor junior talent, refining leadership and knowledge-sharing skills.

• Industry Exposure: Potential to attend industry conferences, participate in thought leadership initiatives, and contribute to Highland's reputation as an innovation leader.

📝 Enhancement Note: The challenges presented are typical for a senior role in a consultancy, focusing on strategic problem-solving, client management, and adapting to new technologies like AI. The growth opportunities are geared towards deepening expertise and expanding influence within the firm and the industry.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex product strategy you developed for a client. What was the challenge, your approach, and the business outcome?" (Focus on your strategic frameworks, research integration, and quantifiable results.)

• "How have you utilized AI tools to accelerate your design or strategy process? Provide a specific example and discuss the impact." (Be ready to detail the AI tools used, the problem they solved, and the measurable benefits.)

Company & Culture Questions:

• "How do you embody Highland's core values of People First, Be Curious, Be Transparent, and Give a Damn in your work?" (Prepare specific anecdotes for each value.)

• "What does 'Human Flourishing' mean to you in the context of digital product design, and how has it influenced your work?" (Show your understanding of the company's foundational principles.)

Portfolio Presentation Strategy:

• Structure for Impact: For each case study, use a clear narrative: Problem -> Your Role/Approach -> Strategy/Methodology (highlighting AI) -> Solution/Outcome -> Learnings.

• Quantify Everything Possible: Use metrics to demonstrate the impact of your work, whether it's user adoption, conversion rates, efficiency gains, or client satisfaction.

• Emphasize AI Integration: Make AI a visible thread throughout your presentation, explaining how and why you used specific AI tools to achieve better results.

• Facilitation & Collaboration: Be prepared to discuss how you facilitated workshops and collaborated with cross-functional teams, perhaps even demonstrating a small interactive element if appropriate.

📝 Enhancement Note: Interview preparation should focus on showcasing strategic thinking, practical application of AI, client leadership, and alignment with Highland's specific values and methodologies. The portfolio presentation is a critical component and should be meticulously prepared to highlight these areas.

📌 Application Steps

To apply for this operations position:

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

• Optimize Your Resume: Tailor your resume to highlight 10+ years of experience in product strategy, UX, and strategic design. Explicitly mention your experience with AI-enabled design, client leadership, and your proficiency with Miro and Figma. Use action verbs and quantify achievements wherever possible.

• Curate Your Portfolio: Select 2-3 impactful projects that demonstrate your strategic leadership, ability to translate insights into roadmaps, and practical application of AI in design and production. Ensure each case study clearly outlines the challenge, your role, methodology, outcomes, and learnings.

• Prepare Your Presentation: Practice presenting your portfolio with a focus on storytelling, strategic rationale, and the quantifiable impact of your work. Be ready to discuss your approach to client engagements and AI integration in detail.

• Research Highland: Thoroughly review Highland's website, understand their approach to "Experiences that Matter," their core values, and their methodology, particularly their use of AI. Prepare to articulate how your skills and experience align with their mission and culture.

⚠️ 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.