Learning Design Manager

📍 Job Overview

Job Title: Learning Design Manager - Technology & Operations

Company: HUB International

Location: Chicago, IL, United States

Job Type: Full-Time

Category: Learning & Development / Operations Enablement

Date Posted: April 30, 2026

Experience Level: 7-10 years

🚀 Role Summary

• Lead and mentor a team of learning designers focused on technology and operations initiatives, emphasizing a user-first approach to learning experience design.

• Develop comprehensive learning strategies for large-scale technology implementations, incorporating adult learning principles and multi-modal delivery methods.

• Manage a diverse portfolio of ~20 concurrent learning projects, ensuring quality, timely delivery, and alignment with business objectives.

• Drive the adoption of agile methodologies within the learning design process and collaborate with Change Enablement teams for integrated project success.

• Oversee Learning Management System (LMS) administration for the Technology & Operations department, ensuring efficient platform utilization.

📝 Enhancement Note: This role sits at the intersection of Learning and Development (L&D) and Operations, specifically focusing on enabling technology and operational transformations through effective learning solutions. The emphasis on "user-first thinking," "technology implementations," and "ROI through data analytics" positions this as a strategic operations enablement function, critical for driving adoption and efficiency in complex organizational changes.

📈 Primary Responsibilities

• Team Leadership & Development: Lead, mentor, and develop a team of approximately 8 learning designers and 1 program analyst, fostering professional growth and building expertise in instructional design principles and emerging learning technologies.

• Learning Strategy Design: Design comprehensive learning strategies for technology implementations (e.g., ERP, CRM, digital transformation), applying adult learning principles to create multi-modal solutions including e-learning, instructor-led training (ILT), microlearning, and performance support tools.

• Immersive Learning Experiences: Seek opportunities to create immersive and engaging learning experiences using simulation and scenario-based training to enhance knowledge retention and application.

• Training Effectiveness Evaluation: Establish and manage robust processes to evaluate the effectiveness of training programs, focusing on user adoption, performance improvement, and return on investment (ROI).

• Project Portfolio Management: Manage a portfolio of approximately 20 concurrent learning projects, ensuring high quality, user-centric design, and on-time delivery across all initiatives.

• Agile Implementation & Risk Management: Implement agile methodologies for learning project management, actively monitor project risks, and coordinate closely with the Change Enablement team for seamless integration with broader change initiatives.

• LMS Administration: Oversee the administration and utilization of the Learning Management System (LMS) specifically for the Technology & Operations department, ensuring data integrity and optimal user experience.

• Stakeholder Partnership & ROI Demonstration: Partner effectively with business leaders to understand critical learning and business needs, present strategic learning plans to senior leadership, and demonstrate the ROI of learning initiatives through rigorous data analytics and performance metrics.

📝 Enhancement Note: The primary responsibilities highlight a blend of people management, strategic learning design, technical proficiency, and operational execution. The emphasis on managing a large project portfolio (~20 concurrent projects) and implementing agile methodologies points to a need for strong operational rigor and process management skills. Demonstrating ROI through data analytics is a key operations-focused outcome.

🎓 Skills & Qualifications

Education: Bachelor's degree (4-year degree) preferred; Master's degree in Instructional Design, Educational Technology, or a related field is also preferred.

Experience:

• 5+ years of proven experience in managing and developing a team.

• 7+ years of progressive experience in instructional design and adult learning theory, with at least 3 years in a leadership capacity.

• Demonstrated track record of successfully developing and implementing training programs for large-scale technology transformations within complex organizations.

Required Skills:

• Team Leadership & Development: Strong people management, coaching, and team-building skills with the ability to foster a high-performing, user-focused learning design team.

• Instructional Design Expertise: Deep expertise in instructional design models (e.g., ADDIE, SAM, Agile) and foundational adult learning principles.

• Learning Technology Proficiency: Proficiency with Learning Management System (LMS) platforms (specifically Cornerstone mentioned), advanced authoring tools (e.g., Articulate Storyline/Rise, Adobe Creative Suite, Camtasia, Canva), and virtual meeting technologies (e.g., MS Teams, Zoom).

• Project Management: Strong project management skills, including planning, execution, risk management, and stakeholder communication, with experience managing multiple concurrent projects.

• Agile Methodologies: Experience implementing and leveraging agile methodologies within a learning development context.

• Data Analytics & Performance Metrics: Ability to utilize learning analytics and performance metrics to measure training effectiveness and demonstrate ROI.

• Communication & Facilitation: Exceptional verbal and written communication, presentation, and facilitation skills, with the ability to engage and influence diverse audiences from frontline staff to senior executives.

• Emotional Intelligence: High emotional intelligence and the ability to navigate organizational politics and influence stakeholders without formal authority.

• Resilience: Demonstrated resilience in managing ambiguity, complexity, and change within a dynamic environment.

Preferred Skills:

• Technology Implementation Background: Experience with technology implementations such as ERP, CRM, and other digital transformation initiatives.

• Industry Experience: Background in the insurance or financial services industry.

• AI Tools: Proficiency in leveraging AI tools to accelerate learning design workflows, enhance decision-making, and drive operational efficiency.

📝 Enhancement Note: The requirements emphasize a blend of leadership, deep instructional design expertise, and practical operational skills. The explicit mention of specific tools like Cornerstone and Articulate, along with agile methodologies and data analytics for ROI, are crucial for candidates to highlight. The preference for AI tool proficiency indicates a forward-looking approach to learning operations.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Instructional Design Case Studies: Showcase 3-5 robust case studies demonstrating the design and development of impactful learning solutions for technology and/or operational initiatives. Each case study should detail the problem, your role, the design process (mentioning methodologies like ADDIE or Agile), the chosen learning solutions (e-learning, ILT, performance support), and measurable outcomes.

• Technology Transformation Examples: Include specific examples of learning programs developed for large-scale technology implementations (e.g., ERP rollout, CRM adoption, digital transformation projects).

• Performance Improvement Focus: Highlight projects where learning interventions directly led to improved performance metrics, increased efficiency, or successful adoption of new technologies or processes. Quantify results whenever possible.

• Multi-modal Solutions: Demonstrate experience creating a variety of learning formats, including e-learning modules, instructor-led training materials, quick reference guides, video tutorials, and performance support tools.

• Process Optimization Examples: If possible, include examples of how you improved learning design processes, implemented new tools or methodologies, or streamlined workflows to increase efficiency and quality.

Process Documentation:

• Workflow Design & Optimization: Evidence of designing and documenting learning development workflows, including stages from needs analysis to evaluation. Showcase how you've optimized these workflows for efficiency and quality.

• Agile Implementation Evidence: Examples of how agile principles were applied to learning project management, including sprint planning, backlog management, and iterative development processes.

• Measurement & Analysis Frameworks: Documentation or examples of frameworks used to measure learning effectiveness, track key performance indicators (KPIs), and analyze learning data to demonstrate ROI and inform future design decisions.

📝 Enhancement Note: For this role, a portfolio is critical. It should not just showcase design skills but also operational rigor. Candidates should be prepared to discuss their process management, how they've handled multiple projects concurrently, and how they've used data to prove the value of their learning initiatives, particularly in the context of technology and operations change.

💵 Compensation & Benefits

Salary Range: $115,000 - $125,000 per year.

📝 Enhancement Note: This salary range is explicitly stated in the job description for California, Colorado, Illinois, Maryland, Minnesota, New York, New Jersey, and Washington states. For other locations, this range serves as a strong benchmark, but actual compensation may vary based on local market conditions and the candidate's specific location within the US. It's important for candidates to research cost of living and typical compensation for Learning Design Managers in their specific location if not listed.

Benefits:

• Comprehensive health, dental, and vision insurance.

• Life and disability insurance coverage.

• Flexible Spending Accounts (FSA) and Health Savings Accounts (HSA).

• 401(k) retirement savings plan.

• Generous paid-time-off (PTO) benefits, including vacation, sick days, and personal days.

• Potential for eligible bonuses, equity, and commissions (depending on specific role scope and performance).

Working Hours: The role is full-time, with an estimated 40 hours per week. Travel is required up to 10-25% of the time, indicating a need for flexibility.

📝 Enhancement Note: The listed benefits are standard for a large organization like HUB International. The mention of potential bonuses, equity, and commissions suggests that performance-based compensation is a factor, aligning with operations-focused roles that drive measurable business impact.

🎯 Team & Company Context

🏢 Company Culture

Industry: Insurance and Employee Benefits Brokerage. HUB International operates within a highly regulated and competitive financial services sector, emphasizing client relationships, risk management, and comprehensive solutions.

Company Size: HUB International is a large enterprise, with over $5 billion in revenue and nearly 20,000 employees across approximately 600 offices in North America. This scale implies a need for standardized processes, robust infrastructure, and strong operational management.

Founded: While the founding date isn't explicitly stated for HUB International as a whole, its significant growth, partly through mergers and acquisitions, suggests a dynamic and evolving corporate history.

Team Structure:

• Learning & Development Focus: The role reports into a department that is part of Information Technology, indicating a strong link between technology initiatives and the learning solutions required to support them.

• Direct Reports: The Learning Design Manager directly manages a team of 5 Senior Learning Designers, 3 Learning Designers, and 1 Senior Learning & Development Program Analyst, totaling 9 direct reports. This is a significant team size, requiring strong leadership and delegation skills.

• Cross-functional Collaboration: Close collaboration is expected with business leaders, the Change Enablement team, and potentially IT project managers, product owners, and subject matter experts (SMEs) to ensure learning strategies are aligned with business needs and technology roadmaps.

Methodology:

• User-Centric Design: The team is expected to foster a "user-first thinking" approach in all learning design efforts.

• Agile Project Management: Implementation of agile methodologies for learning project delivery is a key operational practice.

• Data-Driven Decision Making: Learning effectiveness and ROI are to be demonstrated through data analytics and performance metrics, reflecting an operations-oriented mindset.

• Continuous Improvement: Building team capabilities in emerging learning technologies and fostering a culture of innovation are encouraged.

Company Website: https://www.hubinternational.com/

📝 Enhancement Note: The company's size and industry suggest a formal but evolving corporate environment. The role's placement within IT and its focus on technology transformation highlight its operational importance in driving change and adoption across a large organization. The emphasis on M&A activity implies a continuous need for onboarding and integrating new teams and systems, making effective learning design crucial.

📈 Career & Growth Analysis

Operations Career Level: This is a managerial-level position, overseeing a team and managing a significant portfolio of projects. It sits at a senior level within the Learning & Development function, with a strong operational focus due to its ties to technology and business transformation.

Reporting Structure: The Learning Design Manager reports to a higher-level leader within the Information Technology or L&D department. They will work closely with business leaders and the Change Enablement team, influencing strategy and execution without direct reporting lines to these groups.

Operations Impact: The role's primary impact is enabling successful adoption of new technologies and operational processes across HUB International. By creating effective learning solutions, the manager directly contributes to:

• Reduced time-to-competency for employees.

• Increased user adoption rates for new systems.

• Improved operational efficiency and reduced errors.

• Higher ROI on technology investments.

Growth Opportunities:

• Leadership Advancement: Potential to move into Director-level roles within L&D or Operations, managing larger teams or broader learning functions.

• Specialization: Opportunity to deepen expertise in specific areas like learning technology, AI in learning, or complex change management enablement.

• Cross-Functional Moves: The strong operational and project management aspects of the role could open doors to program management, change management leadership, or even operational strategy roles within HUB International.

• Skill Development: Continuous learning is encouraged through exposure to new technologies, methodologies, and leadership challenges.

📝 Enhancement Note: This role offers significant growth potential by combining leadership with a critical operational function. The ability to manage complex projects, influence stakeholders, and demonstrate quantifiable business impact through learning is a strong foundation for advancement within a large, acquisition-focused company like HUB International.

🌐 Work Environment

Office Type: The job is listed as "TELECOMMUTE" but also specifies a Chicago office location (200 N. La Salle St - Suite 1700). Given the "Remote Status: false" and the need for team leadership and collaboration, this role is likely hybrid, requiring presence in the Chicago office for key meetings, team collaboration, and strategic discussions, with flexibility for remote work. The mention of 10-25% travel further supports a hybrid model.

Office Location(s): Chicago, IL - 200 N. La Salle St - Suite 1700. This is a central business district location, likely offering a professional and collaborative office environment.

Workspace Context:

• Collaborative Environment: The role requires extensive collaboration with direct reports, business leaders, and cross-functional teams. The Chicago office would likely provide spaces conducive to team meetings, workshops, and brainstorming sessions.

• Operations Tools & Technology: Access to standard corporate IT infrastructure, including robust collaboration tools (MS Teams, Zoom), project management software, and the necessary hardware/software for learning design and LMS administration.

• Team Interaction: Opportunities for regular interaction with the learning design team, IT department colleagues, and stakeholders from various business units.

Work Schedule: Standard full-time business hours (approximately 40 hours per week) are expected, with flexibility for remote work. However, project deadlines and critical implementation phases may require adjusted hours or focused work periods, typical in operations and project management roles.

📝 Enhancement Note: The "TELECOMMUTE" designation alongside a specific office address often indicates a hybrid work model. Candidates should clarify expectations regarding in-office days and travel requirements, as this is crucial for operations roles that depend on in-person collaboration for critical project phases and stakeholder engagement.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: HR or Talent Acquisition will likely conduct an initial review of applications and conduct a brief screening call to assess basic qualifications and cultural fit.

• Hiring Manager Interview: A conversation with the hiring manager to delve deeper into experience, leadership style, and alignment with the role's core responsibilities. Be prepared to discuss team management philosophies and project successes.

• Portfolio Review & Presentation: A critical stage where candidates will be asked to present a selection of their best work, focusing on case studies of technology transformations and demonstrated ROI. This is where operational impact and process management skills will be evaluated.

• Team & Stakeholder Interviews: Interviews with direct reports and key stakeholders (e.g., IT project leads, business unit leaders) to assess collaboration skills, influence, and ability to work effectively across departments.

• Final Interview: Potentially a final interview with a senior leader to confirm fit and discuss overall strategic alignment.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 projects that best demonstrate your experience in technology implementations, team leadership, and ROI-driven learning design. Prioritize projects with quantifiable results.

• Structure Your Narrative: For each case study, clearly articulate the business problem, your strategic approach, the learning solutions designed, the implementation process (including any operational challenges and how you overcame them), and the measurable business impact (e.g., adoption rates, efficiency gains, cost savings).

• Highlight Process & Operations: Emphasize your process management skills, use of agile methodologies, and how you integrated learning with broader change enablement efforts. Discuss your approach to LMS administration and data analysis.

• Be Ready for Deep Dives: Anticipate questions about your leadership style, how you develop your team, and your approach to managing a large project portfolio under tight deadlines.

• Showcase AI Proficiency: If you have leveraged AI tools, be prepared to discuss specific examples and the impact on efficiency or quality.

Challenge Preparation:

• Case Study Analysis: Be prepared for a potential case study or scenario-based exercise where you might be asked to outline a learning strategy for a hypothetical technology rollout or operational challenge. Focus on your structured thinking process, data-driven approach, and stakeholder management.

• Process Improvement Scenario: You might be asked to describe how you would improve a learning design process, manage a project risk, or measure the effectiveness of a specific training program.

• Leadership & Team Management: Prepare to discuss how you handle performance issues, motivate teams, and foster a collaborative and innovative work environment.

📝 Enhancement Note: The emphasis on portfolio review and presentation is paramount. Candidates must be ready to not only show what they've done but how they've done it, focusing on process, operational efficiency, and measurable business outcomes. This is where operations-minded candidates will shine.

🛠 Tools & Technology Stack

Primary Tools:

• Authoring Tools: Articulate Storyline/Rise, Adobe Creative Suite (e.g., Captivate), Camtasia, Canva. Proficiency with these is essential for creating engaging e-learning content.

• Virtual Meeting & Collaboration: MS Teams, Zoom. Crucial for remote collaboration, virtual training delivery, and team meetings.

• Project Management Tools: While not specified, experience with tools like Asana, Jira, Trello, or MS Project is highly relevant for managing a portfolio of ~20 concurrent projects and implementing agile methodologies.

• AI Tools: Proficiency in leveraging AI tools to accelerate workflows, enhance decision-making, and drive operational efficiency in learning design.

Analytics & Reporting:

• Learning Management System (LMS): Cornerstone (specifically mentioned). Expertise in administration, reporting, and leveraging LMS data is required.

• Learning Analytics Tools: Ability to extract and analyze data from the LMS and other sources to measure training effectiveness, track KPIs, and report on ROI.

• Data Visualization Tools: Experience with tools like Tableau, Power BI, or even advanced Excel for creating dashboards and reports to communicate performance metrics to leadership.

CRM & Automation:

• CRM Systems: Experience with CRM platforms (e.g., Salesforce) is beneficial, as many technology transformations involve CRM implementations. Understanding how learning supports CRM adoption is key.

• Workflow Automation: Familiarity with concepts of workflow automation within learning development or broader operational processes.

📝 Enhancement Note: The explicit mention of Cornerstone LMS and specific authoring tools is critical. Candidates should be prepared to discuss their experience with these tools in detail and demonstrate how they've used them to drive operational efficiency in learning development and delivery. The mention of AI tools is a forward-looking requirement that signals innovation.

👥 Team Culture & Values

Operations Values: HUB International emphasizes:

• Entrepreneurship: Encouraging initiative, innovation, and a proactive approach to problem-solving within the learning function.

• Teamwork: Fostering collaboration both within the learning team and across departments to achieve common goals.

• Integrity: Upholding ethical standards in all dealings, especially in data handling and reporting on training effectiveness.

• Accountability: Taking ownership of project delivery, team performance, and the measurable impact of learning initiatives.

• Service: A client-focused mindset, ensuring that learning solutions meet the needs of employees and contribute to business success.

Collaboration Style:

• Cross-functional Integration: The role requires seamless collaboration with IT, Change Enablement, and various business units to ensure learning strategies are integrated with broader organizational initiatives.

• Process Improvement Culture: A willingness to continuously review and improve learning design and delivery processes to enhance efficiency and effectiveness.

• Knowledge Sharing: Encouraging a culture where team members share best practices, learnings, and insights to elevate the entire team's capabilities.

📝 Enhancement Note: The company values align well with operations roles that require accountability, efficiency, and a service-oriented approach. The emphasis on teamwork and collaboration is crucial for a role that bridges technology, operations, and employee development.

⚡ Challenges & Growth Opportunities

Challenges:

• Managing Ambiguity & Complexity: Navigating the complexities of large-scale technology transformations and integrating learning into evolving business processes requires resilience and strong problem-solving skills.

• Balancing Multiple Projects: Effectively managing a portfolio of ~20 concurrent learning projects with varying priorities and deadlines requires exceptional organizational and time management skills.

• Demonstrating ROI: Quantifying the impact of learning initiatives, especially in complex, multi-faceted technology projects, can be challenging but is a key expectation.

• Keeping Pace with Technology: The rapid evolution of learning technologies and AI necessitates continuous learning and adaptation to maintain cutting-edge solutions.

• Influencing Without Authority: Effectively driving change and gaining buy-in for learning strategies from senior leaders and diverse stakeholders across the organization.

Learning & Development Opportunities:

• Operations Strategy & Process Excellence: Deepen understanding of operational strategies and how learning directly impacts business efficiency and ROI.

• Emerging Learning Technologies: Opportunity to explore and implement new tools, including AI-powered solutions for learning design and delivery.

• Leadership Development: Formal and informal opportunities to hone leadership skills, manage a growing team, and influence strategic decisions.

• Industry Exposure: Gain exposure to the insurance and financial services industry, understanding its unique learning and operational challenges.

• Cross-functional Exposure: Work closely with IT, Change Management, and business units, broadening understanding of the company's overall operations and strategic objectives.

📝 Enhancement Note: The challenges presented are typical for senior operations and enablement roles. The growth opportunities are significant, particularly for individuals looking to bridge the gap between L&D and core business operations and technology implementation.

💡 Interview Preparation

Strategy Questions:

• "Describe your philosophy for leading a learning design team, especially in the context of supporting large technology transformations." (Focus on user-centricity, team development, and operational delivery.)

• "Walk me through your process for managing a portfolio of ~20 concurrent learning projects. How do you prioritize, mitigate risks, and ensure quality?" (Highlight agile methodologies, project management tools, and communication strategies.)

• "How do you measure the ROI of learning initiatives, particularly for technology implementations? Provide a specific example." (Prepare a case study demonstrating your data analytics skills and ability to link learning outcomes to business impact.)

Company & Culture Questions:

• "Based on your understanding of HUB International, how would you align your team's learning strategies with the company's core values and growth objectives?" (Research HUB's values and recent news/initiatives.)

• "How do you foster a culture of continuous learning and innovation within your team, especially when working with established operational processes?" (Discuss team development, knowledge sharing, and embracing new technologies like AI.)

Portfolio Presentation Strategy:

• Start with Impact: Begin by clearly stating the business problem and the desired outcome for each project.

• Showcase Your Process: Detail your methodology (e.g., ADDIE, Agile), tools used, and how you collaborated with SMEs and stakeholders.

• Quantify Results: Present data and metrics that demonstrate the effectiveness of your learning solutions (e.g., improved performance, adoption rates, efficiency gains, cost savings). Use charts and graphs for clarity.

• Highlight Operational Relevance: Emphasize how your learning solutions supported operational efficiency, technology adoption, or business transformation goals.

• Be Prepared for Q&A: Anticipate detailed questions about your design choices, project management approach, and the data presented.

📝 Enhancement Note: Candidates should prepare to discuss their experience through a lens of operational impact and process efficiency. Demonstrating how they manage complex projects, leverage technology, and drive measurable business results will be key to success in this role.

📌 Application Steps

To apply for this Learning Design Manager position:

• Submit your application through the provided link on the HUB International Workday portal.

• Curate Your Portfolio: Select 3-5 of your strongest instructional design case studies, specifically highlighting experience with technology implementations, team leadership, and demonstrable ROI. Ensure these showcase your process management skills and understanding of operational impact.

• Tailor Your Resume: Optimize your resume to clearly articulate your experience in instructional design, adult learning theory, team management, project portfolio management, and proficiency with relevant tools (LMS, authoring tools, Agile). Use keywords from the job description.

• Prepare Your Presentation: Practice walking through your selected portfolio projects, focusing on the problem, your solution, the process, and the measurable business outcomes. Be ready to discuss your leadership style and operational approach.

• Research HUB International: Familiarize yourself with HUB's industry, core values, recent news, and their approach to technology and employee development. Understand how your role contributes to their overall business objectives.

⚠️ 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.