Director of Learning & Development

TrueNorth Companies, L.C. • Cedar Rapids, IA

1d • Hybrid

About The Position

TrueNorth is seeking a Director of Learning & Development to join its team in Cedar Rapids, Iowa. The Director will develop and lead an enterprise-wide learning and development strategy that advances TrueNorth’s vision of a lifetime learning organization, strengthens the TrueNorth Way service philosophy, and supports client trust, profitable organic growth, and long-term perpetuation. The position works across business units and leadership levels to build learning opportunities that support organizational and divisional objectives.

The role oversees staff learning and development programs, including leadership development, performance management, career development, the technical insurance academy, new-leader training, and producer development. It also owns the internal training information system and career development program, maintains and evaluates learning content, measures program effectiveness, supports change management, and advances AI and data fluency. The Director partners with leaders, colleagues, community organizations, and external learning providers to identify needs and provide relevant development opportunities. The position also leads direct reports, helps forecast and manage training budgets, and travels to regional offices as needed.

Requirements

• Bachelor’s degree.
• Ten or more years of professional work experience in training, development, higher education, and/or academia.
• Proficiency with Microsoft Office, including Word, Excel, Outlook, SharePoint, and PowerPoint.
• Prior project management experience.
• Five or more years of direct leadership experience.
• AI proficiency or experience with ChatGPT and/or Copilot’s Excel, PowerPoint, Word, and search functions.
• Senior-level accountability, sound judgment, integrity, and professional discretion.
• Strategic leadership, business acumen, and ability to translate strategy into action.
• Advanced knowledge application, including broad business expertise and deep functional expertise.
• Strong executive presence, communication, interpersonal effectiveness, and ability to inspire others.
• Ability to influence decisions, build relationships, negotiate, and create impact across organizational levels.
• People leadership skills, including delegation, performance management, mentorship, coaching, and talent development.
• Adaptability and change leadership skills, including the ability to navigate complexity, ambiguity, and organizational transitions.
• Critical thinking, innovation, conceptualization, problem-solving, and effective prioritization.
• Client-centric and culturally aware approach focused on collaboration, service, and business value.
• Financial acumen, project management, independent execution, and consistent achievement of goals and commitments.

Nice To Haves

• Experience with Learning Management Systems.
• Familiarity with training and adult education platforms; prior experience implementing and supporting them is ideal.
• Background in insurance and/or sales.
• Licenses and/or certifications, as necessary.

Responsibilities

• Set the strategic direction for staff learning and development and manage the annual learning calendar for divisions and areas of focus.
• Administer, manage, design, and facilitate training programs that support TrueNorth’s strategies, including remote learning, leadership programs, performance management, and career development.
• Meet with leaders to identify and prioritize educational objectives for specific roles and individuals, and align third-party vendors and resources to support those objectives.
• Oversee the technical insurance academy, which builds foundational knowledge and technical expertise and prepares colleagues to deliver consistent advice and exceptional client service.
• Provide leaders and colleagues with coaching tools, development resources, and expectations that encourage shared responsibility for learning and ownership of individual development.
• Partner with leaders to respond to training needs and proactively develop strategic team solutions.
• Design, maintain, curate, customize, facilitate, and localize internal and external course content, with a primary focus on corporate values and standards.
• Align the learning and development vision with leadership levels and firm and divisional objectives, and own the Annual Leadership Development Calendar.
• Build relationships with community partners and external learning providers to expand development opportunities, strengthen talent referral pathways, and support TrueNorth’s reputation as a place to build a career.
• Maintain working knowledge of business-unit products, services, and standards, and make relevant development opportunities available, including designations, training, conferences, presentations, and experiential learning.
• Enhance, facilitate, and increase participation in the new-leader training series for new and aspiring leaders.
• Develop, implement, monitor, plan, and measure program effectiveness, engagement, quality, and training outcomes.
• Oversee branding and long-term documentation for the internal certification process.
• Support guest presenters at the Cedar Rapids office, including planning, event preparation, attendance, online meeting or presentation proctoring, technology coordination, guest welcomes, and food orders.
• Contribute to producer development plans that build sales capabilities, business acumen, and entrepreneurial skills to support specialized niche practices.
• Own the internal training information system, including the career development program.
• Analyze course content and evaluate programs; recommend curriculum improvements to meet audience needs, particularly in AI, insurance, leadership development, and sales, and partner with third-party vendors as appropriate.
• Direct change-management learning and support to help leaders prepare colleagues for organizational changes, communicate expectations, and build skills for new ways of working.
• Welcome new colleagues by coordinating an individualized training plan with teammates.
• Advance AI and data fluency through practical learning that supports responsible technology use, better decisions, and capacity for work requiring human judgment and relationships.
• Ensure timely communication, engagement, and adoption of the learning and development calendar and offerings, including pre-training reminders and post-training follow-up.
• Assist with managing and facilitating resources from consulting partnerships and integrate relevant concepts throughout learning and development activities and strategy.
• Serve as the expert in DiSC and other screening or assessment approaches used for development, team building, and working relationships.
• Work with leadership to forecast and manage business-unit training budgets, track and report spending, and allocate funds billed to the Learning and Development department.
• Travel to and collaborate with regional offices as needed to align processes, initiatives, and practices.
• Lead, motivate, support, and develop direct reports, addressing concerns and providing coaching when needed.

Benefits

• Annual bonus.
• Medical, dental, vision, life, and disability insurance.
• 401(k) with company contributions.
• Responsible Time Off (RTO), with flexible time off and a required minimum to ensure rest and balance.
• 11 paid holidays.
• Paid volunteer time off and donation match program.
• Tuition reimbursement and paid certifications, licenses, and designations.
• Employee Assistance Program (EAP) and wellness program with financial incentives.
• Hybrid work schedule.
• $3,000 referral bonus.

What This Job Offers

• Job Type: Full-time
• Career Level: Director