Senior Manager, Digital Delivery & Automation

HUB International’s National Employee Benefits and Retirement Team is dedicated to driving growth and excellence across Canada by supporting our regional teams. As strategic partners, this team collaborates with local offices to expand and enhance our Employee Benefits and Retirement divisions, ensuring we deliver best-in-class solutions for clients nationwide. Through innovative strategies, expert guidance, and a shared commitment to success, the National Team empowers our regions to meet evolving market demands, strengthen client relationships, and achieve sustainable growth in the benefits and retirement space. About The Role This role is responsible for overseeing the planning, execution, and successful delivery of digital and automation projects across Canadian Employee Benefits & Retirement (EB&R). The Manager will lead all automation and efficiency initiatives spanning both Employee Benefits (EB) and Group Retirement Services (GRS), with a specific focus on automating complex documents that require data inputs from multiple sources. This individual will manage the full project lifecycle — from requirements definition through delivery and post-implementation support — while ensuring alignment with stakeholder expectations, agile best practices, and organizational strategic goals. What You’ll Do Project and Product Delivery: Plan, define, and deliver digital and automation solutions for EB&R — including automation of client-facing documents, such as: Renewals, Mid-Year Reviews, Claims Experience Reports, and Stewardship Reports — ensuring alignment with strategic goals and user needs. Team Leadership: Lead, motivate, and manage a multidisciplinary team (including a direct-report developer), as well as third-party suppliers where applicable, fostering collaboration and continuous improvement. Stakeholder Engagement: Act as the primary liaison between digital/automation teams, EB and GRS business stakeholders, and other project managers, managing expectations and cross-team dependencies. Project Facilitation: Champion best practices, remove blockers, oversee iterative planning, and ensure teams follow agile delivery and process-improvement standards. Risk and Quality Management: Ensure projects meet quality standards, comply with relevant regulations, and are delivered on time and within budget. Change and Service Management: Support service modernization, manage change initiatives, and maintain ongoing support for digital and automation solutions post-implementation. What You’ll Need for Success Degree in IT, Digital, or Management, or equivalent professional experience. Professional certifications such as PRINCE2, Agile (or equivalent) are often desirable. Experience managing complex, high-risk digital/automation projects and leading multidisciplinary teams is essential. Experience within Employee Benefits, Group Retirement Services, or the broader insurance/financial services industry is an asset Strategic and Tactical Thinking: Ability to plan at a high level while managing day-to-day project execution. Analytical and Organizational Skills: Strong problem-solving, prioritization, and resource-management capabilities. Communication and Collaboration: Excellent interpersonal skills to engage stakeholders, coach team members, and facilitate cross-functional collaboration. Technical Awareness: Understanding of digital solutions, automation technologies, emerging tech, and system integration processes. Expertise: Experience in agile project delivery is an asset. What’s in it for you? Your well-being is our priority, and we back this up with a wealth of benefits: Competitive Compensation: Benefit from a pay structure that includes incentives, bonuses, and opportunities to increase your earnings. Work-Life Balance: Enjoy flexible work arrangements and generous time off to support your personal and professional life. Tailored Benefits: Access a personalized benefits package, including company-matched RRSPs, designed to meet your unique needs. Career Growth and Support: Invest in your future with HUB! Take advantage of our sponsored training and development programs, tuition reimbursement opportunities, and coverage for professional license fees and membership dues—everything you need to support your growth and excel in your career. Exclusive Perks: Take advantage of discounts on events, travel, accommodations, and personal home & auto insurance. At HUB, we believe that diversity drives innovation, equity fosters opportunity, and inclusion creates a culture where everyone thrives. We are committed to building a workplace that reflects the communities we serve and where every employee feels valued, respected, and empowered to bring their whole self to work. By embracing diverse perspectives and fostering an inclusive environment, we cultivate a collaborative and dynamic team that delivers exceptional results for our clients and communities. Compensation The expected salary range for this position is $95,000-$120,000 and will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. Why Choose HUB? When you choose HUB, you're choosing a competitive, exciting, and friendly work environment that strategically positions you for longevity and offers significant advancement, growth, and success opportunities. To read more about HUB, please visit - About Us - HUB International About HUB International Headquartered in Chicago, Illinois, Hub International Limited is a leading full-service global insurance broker and financial services firm providing risk management, insurance, employee benefits, retirement and wealth management products and services. With more than 19,000 employees in offices located throughout North America, HUB’s vast network of specialists brings clarity to a changing world with tailored solutions and unrelenting advocacy, so clients are ready for tomorrow. We’re not just an insurance broker, we’re a team of passionate professionals dedicated to innovation, excellence, and empowering our clients and communities through personalized support and expertise. If you’re interested in learning how you can grow your career at HUB, visit our Careers Page to explore our opportunities. AI Disclosure AI and Automation Notice HUB International uses limited AI and automation tools within our recruitment systems to enhance efficiency in the hiring process and in the candidate experience. These tools do not independently make hiring decisions or screen out candidates — all decisions are made through human review. HUB International is committed to creating an inclusive and accessible recruitment process for all candidates. If you require accommodations at any stage of the interview process, please let us know, and we will work with you to ensure a fair and equitable experience. #LI-hybrid #LI-SS1 Department Information Technology Required Experience: 7-10 years of relevant experience Required Travel: Up to 25% We endeavor to make this website accessible to any and all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please contact the recruiting team . 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