Learning Design Manager - Technology & Operations

📍 Job Overview

Job Title: Learning Design Manager - Technology & Operations Company: HUB International Location: Chicago, IL Job Type: Full-Time Category: Learning & Development Operations / GTM Enablement Date Posted: October 1, 2025 Experience Level: 5-10 Years Remote Status: Hybrid

🚀 Role Summary

• Lead and mentor a team of learning design and development professionals to create impactful learning experiences for technology adoption initiatives.
• Drive technology mastery across a large employee base through innovative and comprehensive learning strategies aligned with organizational transformation goals.
• Design and implement multi-modal learning solutions, including e-learning, instructor-led training, microlearning, and performance support tools, with a focus on immersive and scenario-based training.
• Manage a significant portfolio of concurrent learning projects, ensuring high quality, user-centric delivery, and adherence to agile methodologies.

📝 Enhancement Note: This role sits within the Technology & Operations function, indicating a strong focus on enabling employees to effectively use new systems and processes. The emphasis on "user-first thinking," "technology adoption," and "organizational transformation" suggests this is a critical GTM enablement function, directly impacting operational efficiency and employee productivity. The direct reports list also highlights a significant team management component for this role.

📈 Primary Responsibilities

• Lead, mentor, and develop a team of approximately 10 learning designers and analysts, fostering a culture of user-centric design and continuous improvement.
• Build and enhance team capabilities in advanced instructional design principles, adult learning theories, and emerging learning technologies.
• Develop comprehensive learning strategies for large-scale technology implementations, ensuring alignment with business objectives and organizational change management efforts.
• Design and oversee the creation of diverse learning materials, including e-learning modules, instructor-led training (ILT) content, microlearning assets, and performance support tools, with a focus on immersive simulations and scenario-based learning.
• Establish, manage, and refine processes for evaluating the effectiveness and impact of training programs, utilizing data analytics and performance metrics to demonstrate ROI.
• Oversee the management of a portfolio of approximately 20 concurrent learning projects, ensuring timely, high-quality, and user-focused delivery through agile methodologies.
• Implement and monitor agile project management practices, identify and mitigate project risks, and coordinate closely with the Change Enablement team for integrated initiative delivery.
• Manage and administer the Learning Management System (LMS) specifically for the Technology & Operations department, ensuring efficient content deployment and user tracking.
• Collaborate proactively with business leaders to understand evolving learning and business needs, present strategic learning solutions, and articulate the ROI of learning initiatives.

📝 Enhancement Note: The primary responsibilities emphasize a blend of strategic leadership, team management, hands-on learning design oversight, and project portfolio management. The mention of "agile methodologies" and "integrated initiatives" with Change Enablement points to a dynamic and collaborative work environment typical in fast-paced GTM and operational transformation projects.

🎓 Skills & Qualifications

Education:

• Bachelor's degree preferred in fields such as Instructional Design, Educational Technology, Learning & Development, or a related discipline.
• Master's degree in Instructional Design, Educational Technology, or a related field is also preferred, indicating a desire for advanced theoretical knowledge.

Experience:

• 7+ years of progressive experience in instructional design and adult learning theory, with a strong emphasis on practical application in corporate environments.
• Minimum of 3 years in a leadership or management role, with proven experience leading and developing teams of learning professionals.
• Demonstrated track record of successfully supporting users through large-scale technology transformations within complex organizational structures.

Required Skills:

• Deep expertise in instructional design models such as ADDIE, SAM, and Agile methodologies, with the ability to apply them effectively.
• Profound understanding of adult learning principles and their application in designing engaging and effective learning experiences.
• Proficiency with Learning Management Systems (LMS) for administration, content deployment, and reporting.
• Strong command of authoring tools, including Articulate Suite (Storyline, Rise), Adobe Creative Suite, Camtasia, and potentially Canva for visual design.
• Experience with virtual classroom technologies (e.g., Zoom, Teams, Webex) for delivering live training sessions.
• Proficiency in learning analytics and data analysis to measure training effectiveness and demonstrate ROI.
• Exceptional communication, presentation, and facilitation skills, with the ability to engage diverse audiences.
• High emotional intelligence and strong interpersonal skills to navigate organizational politics and build relationships.
• Demonstrated capability to influence stakeholders at all levels, even without direct authority.
• Resilience and adaptability in managing ambiguity, complexity, and change.
• Background in supporting technology implementations, including ERP, CRM, and broader digital transformation initiatives.

Preferred Skills:

• Experience within the insurance or financial services industry, which can provide valuable context for industry-specific learning needs.

📝 Enhancement Note: The requirement for 7+ years of experience with 3+ years in leadership, combined with a preference for a Master's degree, positions this as a mid-to-senior level management role. The emphasis on specific instructional design models, authoring tools, and experience with large-scale tech transformations signals a need for practical, hands-on expertise in a corporate learning and development setting.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase examples of comprehensive learning strategies for technology implementations, demonstrating how you've addressed user adoption challenges.
• Present case studies of multi-modal learning solutions (e-learning, ILT, microlearning, performance support) and highlight the rationale behind the chosen modalities.
• Include examples of how you've used simulation and scenario-based training to create immersive and effective learning experiences.
• Demonstrate experience in establishing and managing processes for evaluating training effectiveness, including data collection and impact analysis.
• Provide evidence of successfully managing a portfolio of multiple concurrent learning projects, showcasing project management methodologies and delivery timelines.

Process Documentation:

• Detail your approach to applying agile methodologies in learning design and development projects, including sprint planning, risk management, and stakeholder communication.
• Illustrate your process for collaborating with Change Enablement teams on integrated initiatives, ensuring seamless communication and coordinated delivery.
• Explain your system for overseeing LMS administration, including content uploading, user management, reporting, and troubleshooting.
• Outline your methodology for partnering with business leaders to understand needs, present strategies, and demonstrate learning ROI through data analytics and performance metrics.

📝 Enhancement Note: For a Learning Design Manager role, a strong portfolio is crucial. It should not only display the quality of learning materials but also the strategic thinking behind them, the project management rigor, and the ability to measure impact. Candidates should be prepared to discuss the "why" behind their design choices and the "how" of their process management.

💵 Compensation & Benefits

Salary Range:

• The disclosed salary range for this position is $120,000 to $150,000 USD annually.
• This range is subject to adjustment based on factors such as the successful candidate's skills, experience level, and specific working location, as well as the business line, scope, and level of the position.

Benefits:

• Comprehensive health, dental, and vision insurance plans.
• Life and disability insurance coverage.
• Flexible Spending Accounts (FSA) and Health Savings Accounts (HSA) for healthcare expense management.
• 401(k) retirement savings plan, likely with employer matching contributions.
• Paid Time Off (PTO) benefits, including vacation, sick days, and personal days.
• Potential for eligible bonuses, equity participation, and commissions, depending on the specific role and performance.

Working Hours:

• Full-time position, typically aligning with standard business hours.
• The role is based in Chicago, IL, with a preferred hybrid work arrangement.
• The job description mentions "40" as the standard working hours per week.

📝 Enhancement Note: The salary range provided is a competitive market rate for a Learning Design Manager with significant leadership and technical expertise in a major metropolitan area like Chicago. The inclusion of equity and commissions suggests potential for performance-based compensation beyond the base salary, which is common for roles that directly impact revenue enablement or operational efficiency. The hybrid arrangement offers a balance between in-office collaboration and remote flexibility.

🎯 Team & Company Context

🏢 Company Culture

Industry: Insurance and Employee Benefits Brokerage. HUB International operates as a global leader in this sector, providing a wide array of business and personal insurance, employee benefits, and risk management services. Company Size: Approximately 20,000 employees across nearly 600 offices in North America, with over $5 billion in revenue. This signifies a large, established organization undergoing significant growth, partly through mergers and acquisitions. Founded: HUB International has a history of substantial growth, suggesting a dynamic and evolving corporate environment.

Team Structure:

• The Learning Design Manager reports to the Director of Learning and Change Enablement, indicating a dedicated L&D function within the broader organization.
• This role directly manages a team of approximately 10 individuals, including Senior Learning Designers, Learning Designers, and a Senior Learning & Development Program Analyst.
• Cross-functional collaboration is expected with business leaders, Change Enablement teams, and potentially IT and HR departments.

Methodology:

• Emphasis on "user-first thinking" in learning design, prioritizing the needs and experience of the end-user.
• Adoption of agile methodologies for project management, promoting flexibility and iterative development.
• A data-driven approach to evaluating learning effectiveness and demonstrating ROI through analytics and performance metrics.
• Focus on continuous learning and development, both for the team and the broader employee base, to support organizational transformation.

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

📝 Enhancement Note: HUB International's description as a "team of entrepreneurs" and its focus on protecting "aspirations" suggests a culture that values initiative, client focus, and growth. The company's significant size and M&A activity imply a need for robust and scalable learning solutions to onboard new employees and integrate new systems and processes effectively. The L&D team plays a critical role in this integration and growth.

📈 Career & Growth Analysis

Operations Career Level: This role is a management position within the Learning & Development (L&D) function, specifically focused on technology and operations enablement. It sits at a mid-to-senior management level, responsible for a team and a significant project portfolio. Reporting Structure: The Learning Design Manager reports to the Director of Learning and Change Enablement. This indicates a clear hierarchy within the L&D department, with potential for upward mobility to Director-level roles or specialized leadership positions within broader HR or Transformation functions. Operations Impact: This role has a direct impact on the operational efficiency and productivity of HUB's 20,000+ employees by ensuring successful technology adoption. Effective learning design and implementation directly contribute to reducing errors, increasing process adherence, improving employee performance, and accelerating the realization of benefits from technology investments. This role is crucial for driving the successful adoption of GTM and operational technologies.

Growth Opportunities:

• Leadership Advancement: Potential to advance to a Director of Learning & Development role, overseeing larger teams or broader L&D functions, or to specialized leadership roles in areas like Change Management or Digital Transformation Enablement.
• Skill Specialization: Opportunity to deepen expertise in cutting-edge learning technologies, AI in learning, advanced analytics for learning impact, and complex change management strategies.
• Strategic Influence: Grow into a more strategic advisory role, influencing the company's overall approach to technology adoption, employee development, and organizational change.
• Cross-Functional Mobility: Potential to move into other leadership roles within HR, Operations, or specific business units by leveraging a strong understanding of business processes and employee enablement.

📝 Enhancement Note: The role's focus on technology and operations enablement within a large, growing company offers significant career advancement potential. The blend of people management, strategic planning, and technical learning expertise makes candidates well-rounded for future leadership opportunities.

🌐 Work Environment

Office Type: The role is based in Chicago, IL, with a preferred hybrid work arrangement. This suggests a modern office environment designed to support collaboration and focused work. Office Location(s): Chicago, IL - 200 N. La Salle St - Suite 1700. This is a prime downtown Chicago location, indicating a professional and accessible office setting. Workspace Context:

• The hybrid model allows for a blend of in-office collaboration with team members and business partners, and remote work for focused design and analysis tasks.
• The office environment likely provides access to necessary technology, meeting spaces, and resources to support learning design and development activities.
• Opportunities for direct interaction with the learning design team, the Director of Learning, and various stakeholders across technology and operations departments are inherent in the role.

Work Schedule:

• Standard full-time hours are expected, likely around 40 hours per week.
• The hybrid arrangement offers flexibility, allowing employees to balance in-office and remote work, which can be beneficial for managing deep work sessions required for learning design and analysis.

📝 Enhancement Note: The hybrid work model in a major city like Chicago is attractive for talent acquisition and retention. It balances the need for in-person collaboration essential for team management and stakeholder engagement with the flexibility that many professionals seek for focused work.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Likely a phone or video call with an HR representative or recruiter to assess basic qualifications, salary expectations, and cultural fit.
• Hiring Manager Interview: A deeper dive into your experience, leadership style, and approach to learning design and team management. Expect questions about your experience with technology transformations and managing learning portfolios.
• Team/Stakeholder Interviews: Meetings with direct reports, peers, and key stakeholders (e.g., IT leaders, Operations managers) to evaluate collaboration skills, leadership approach, and understanding of business needs.
• Portfolio Presentation/Case Study: A critical stage where you will be asked to present examples from your portfolio, demonstrating your instructional design philosophy, project management capabilities, and ability to measure impact. Be prepared to discuss a specific technology implementation and the learning strategy you developed.
• Final Interview: May involve senior leadership or the Director of Learning to make a final decision based on overall fit and strategic alignment.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your most impactful projects, focusing on those involving technology adoption, large-scale transformations, or complex business challenges.
• Structure for Impact: For each project, clearly articulate the business problem, your role and responsibilities, the learning objectives, your design strategy (including modalities and rationale), the project management approach, and quantifiable results (ROI, adoption rates, performance improvements).
• Highlight Process: Be ready to discuss your design process (e.g., ADDIE, Agile), your approach to needs analysis, content development, pilot testing, and evaluation.
• Showcase Leadership: If possible, include examples of how you've mentored or developed team members, managed project timelines, or navigated stakeholder challenges.
• Technology Focus: Ensure examples clearly demonstrate your expertise in designing learning for technology implementations.

Challenge Preparation:

• Be prepared for a potential case study or simulation exercise. This could involve analyzing a learning need for a new technology, designing a learning intervention, or outlining a strategy for measuring training effectiveness.
• Practice articulating your thought process and strategic reasoning clearly and concisely.
• Understand HUB International's business and industry to tailor your responses and demonstrate a genuine interest.
• Prepare questions that demonstrate your understanding of the role, the team, and the company's strategic objectives related to technology and learning.

📝 Enhancement Note: The emphasis on portfolio presentation and case studies for this role is significant. Candidates should prepare to not only show what they've done but also explain their strategic thinking, process, and measurable impact, especially concerning technology adoption and operational improvement.

🛠 Tools & Technology Stack

Primary Tools:

• Authoring Tools: Articulate Suite (Storyline, Rise), Adobe Creative Suite, Camtasia, Canva. Proficiency in these is essential for creating e-learning, video, and visual assets.
• Virtual Classroom Technologies: Zoom, Microsoft Teams, Webex, or similar platforms for delivering synchronous training sessions.
• Learning Management System (LMS): Experience with LMS administration is required, and familiarity with specific platforms (e.g., Workday Learning, Cornerstone OnDemand, Docebo) would be beneficial.
• Project Management Software: Familiarity with tools like Asana, Trello, Jira, or Monday.com for managing agile projects and team workflows.

Analytics & Reporting:

• Learning Analytics Tools: Experience with LMS reporting capabilities, and potentially broader analytics platforms (e.g., Tableau, Power BI) to analyze learning data and demonstrate ROI.
• Data Analysis Tools: Proficiency in Excel for data manipulation and analysis is assumed.

CRM & Automation:

• CRM Systems: While not directly managed, understanding how CRM systems (e.g., Salesforce) are used in a business context can be helpful for designing sales enablement or customer-facing technology training.
• Automation Tools: Familiarity with workflow automation concepts can be beneficial when discussing efficiency improvements in learning delivery or administration.

📝 Enhancement Note: The specific mention of authoring tools and LMS administration highlights the technical backbone of this role. Candidates with experience in these areas will be well-positioned. The inclusion of data analytics tools suggests a move towards more data-driven L&D strategies.

👥 Team Culture & Values

Operations Values:

• Entrepreneurship: Encouraging initiative, innovation, and a proactive approach to problem-solving in learning design and delivery.
• Teamwork: Fostering a collaborative environment where team members support each other, share knowledge, and work together to achieve common goals.
• Integrity: Upholding ethical standards in all learning development and interactions, ensuring accuracy and transparency.
• Accountability: Taking ownership of projects, deliverables, and team performance, with a focus on delivering measurable results.
• Service: A commitment to serving internal stakeholders and employees by providing high-quality, effective learning solutions that support their success.

Collaboration Style:

• Cross-functional Integration: Actively partnering with IT, Operations, HR, and business unit leaders to understand needs and ensure learning solutions are aligned with business objectives.
• User-Centric Feedback Loops: Regularly seeking and incorporating feedback from end-users and stakeholders to refine learning content and strategies.
• Knowledge Sharing: Promoting a culture of sharing best practices, lessons learned, and emerging trends within the L&D team and across relevant departments.
• Agile & Iterative: Embracing an iterative approach to learning development, allowing for flexibility and continuous improvement based on feedback and performance data.

📝 Enhancement Note: The core values of HUB International emphasize a dynamic, client-focused, and accountable work environment. For this role, it means leading a team that is not just creating training, but actively contributing to the company's growth and operational excellence through effective employee enablement.

⚡ Challenges & Growth Opportunities

Challenges:

• Managing a Large, Diverse Workforce: Designing learning solutions that cater to the varied needs and technical proficiencies of 20,000+ employees across different roles and regions.
• Rapid Technology Evolution: Keeping pace with the rapid pace of technological change and ensuring learning content remains relevant and effective.
• Measuring ROI: Quantifying the impact of learning initiatives on business outcomes and demonstrating tangible ROI to leadership, especially in a complex organizational structure.
• Balancing Project Demands: Effectively managing a portfolio of ~20 concurrent projects, prioritizing effectively, and ensuring quality delivery under tight deadlines.
• Change Management Integration: Seamlessly integrating learning strategies with broader change management efforts to drive successful technology adoption and minimize resistance.

Learning & Development Opportunities:

• Advanced Learning Technologies: Exploring and implementing emerging learning technologies, such as AI-powered learning platforms, immersive VR/AR experiences, and advanced simulation tools.
• Data Science in L&D: Developing deeper expertise in learning analytics and data science to drive more sophisticated impact measurement and personalized learning paths.
• Leadership Development: Opportunities for formal leadership training and mentorship to further hone management and strategic planning skills.
• Industry Certifications & Conferences: Participating in relevant L&D and technology conferences (e.g., ATD, DevLearn) and pursuing certifications to stay current with industry best practices.
• Strategic Impact: Contributing to high-level discussions on talent development, digital transformation, and organizational effectiveness.

📝 Enhancement Note: The challenges presented are typical for a senior L&D role in a large, dynamic organization undergoing significant technological change. The growth opportunities emphasize continuous learning and strategic contribution, aligning with the evolving landscape of corporate learning and development.

💡 Interview Preparation

Strategy Questions:

• "Describe your approach to developing a comprehensive learning strategy for a major ERP system implementation across 20,000 employees. How would you involve stakeholders and measure success?" (Focus on strategic planning, stakeholder engagement, and impact measurement).
• "How do you foster a culture of user-first thinking and continuous improvement within a learning design team? Provide specific examples." (Focus on team leadership, process improvement, and user-centric design philosophy).
• "Walk me through a time you had to manage conflicting priorities across multiple learning projects. How did you decide what to focus on, and what was the outcome?" (Focus on project management, prioritization, and risk mitigation).

Company & Culture Questions:

• "Based on your understanding of HUB International and the insurance industry, what do you see as the biggest learning challenges related to technology adoption?" (Demonstrates research and industry understanding).
• "How would you ensure your learning solutions align with HUB's core values of entrepreneurship, teamwork, integrity, accountability, and service?" (Focus on cultural fit and value alignment).
• "Describe a situation where you had to influence senior leadership to gain buy-in for a learning initiative. What was your strategy, and what was the result?" (Focus on influence, communication, and stakeholder management).

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly outline the problem, your solution (design strategy, modalities used), your execution (project management, team involvement), and the measurable impact (KPIs, ROI, adoption rates).
• Quantify Achievements: Use specific numbers and data points to demonstrate the success of your projects.
• Explain Your 'Why': Be prepared to articulate the rationale behind your design choices and methodologies.
• Highlight Leadership: Showcase how you led your team, managed resources, and collaborated with stakeholders.
• Tailor to HUB: Connect your experience and portfolio examples to HUB International's business, industry, and stated values where possible.

📝 Enhancement Note: Interview preparation for this role should focus on demonstrating strategic thinking, strong leadership, practical application of learning design principles, and the ability to measure and articulate impact, especially within the context of technology adoption and operational efficiency.

📌 Application Steps

To apply for this Learning Design Manager position:

• Submit your application through the provided Workday link: https://hubinternational.wd1.myworkdayjobs.com/HUBInternational/job/Chicago-IL/Learning-Design-Manager---Technology---Operations_R0032325-1
• Curate Your Portfolio: Select 3-5 of your most relevant projects, emphasizing technology implementations and team leadership. Prepare detailed case studies that highlight your strategic approach, design process, and measurable impact.
• Optimize Your Resume: Ensure your resume clearly articulates your experience in instructional design, adult learning theory, team leadership, project management, and your proficiency with relevant authoring tools and LMS platforms. Use keywords from the job description.
• Prepare for Portfolio Presentation: Practice presenting your case studies clearly and concisely, focusing on the "why" behind your decisions and the quantifiable results. Be ready to discuss your leadership style and approach to team development.
• Research HUB International: Familiarize yourself with HUB's business, industry, core values, and recent growth initiatives. Understand their approach to technology and employee development.

⚠️ 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.