Vice President, Learning & Development

Alera Group • Chicago, IL

6d • Remote

About The Position

We’re seeking a visionary Vice President of Learning & Development to shape the strategy, elevate leadership capability, and accelerate growth across our organization. In this high‑impact role, you’ll champion a culture of continuous learning, architect innovative development programs, and partner with leaders at every level to prepare our workforce for what’s next. If you’re passionate about transforming talent and building enterprise-wide capability, this is your opportunity to lead the way.
Alera Group was founded in 2017 and has grown to become the 14th largest broker of US business. We are passionate about our clients’ success in the areas of Employee Benefits, Property and Casualty Insurance, Retirement Plan Services, and Wealth Services. With a network of offices nationwide, our commitment to collaboration allows us to offer national resources combined with local service.
The Vice President of Learning & Development (L&D) will be responsible for driving the learning strategy, programs, and initiatives that enhance the skills, knowledge, and leadership capabilities of colleagues across all levels of the organization. This role is essential to fostering a culture of continuous learning, ensuring that colleagues are well-prepared to meet current and future business demands. The VP will lead the development and execution of comprehensive learning programs, leadership development, organizational development, succession planning, and career progression initiatives that align with the company’s strategic goals.
As a key member of the HR leadership team, the VP of Learning & Development will collaborate with business leaders across the organization, including sales, account management, operations, shared services, and compliance, to develop tailored learning programs that address the specific needs of each function. The role also requires a deep understanding of industry trends, best practices in L&D, and an innovative approach to delivering high-impact learning solutions.
As VP of Learning & Development, you’ll shape a company‑wide strategy that builds stronger leaders, sharpens skills, and drives a culture of continuous growth. Partnering across the business, you’ll design innovative, high‑impact programs that prepare our teams to meet today’s needs and tomorrow’s opportunities. If you’re driven to transform talent into performance, this role puts you at the center of that impact.

Requirements

• Bachelor’s degree in Human Resources, Organizational Development, Business, or related field (Master’s degree preferred).
• 10+ years of experience in learning and development, with at least 5 years in a senior leadership role.
• Proven track record of developing and implementing L&D strategies in a large, multi-regional organization.
• Strong knowledge of learning methodologies, including instructional design, leadership development, and adult learning principles.
• Experience managing LMS platforms and other learning technologies.
• Demonstrated success in driving leadership development and managing succession planning efforts.
• Excellent project management and organizational abilities.
• Exceptional communication, presentation, and influence skills to engage and motivate senior leaders and frontline sales teams.
• Results-driven with a proactive and hands-on approach to driving initiatives.
• Adaptable and able to thrive in a fast-paced, dynamic environment.
• Strong leadership presence with the ability to inspire and influence at the office, regional, and executive level.
• Collaborative mindset, with a commitment to fostering a positive and inclusive company culture.
• Understanding of various learning methodologies and proven ability to tailor training programs accordingly.

Nice To Haves

• Experience in the insurance industry or a similarly regulated environment is preferred.

Responsibilities

• Develop and lead the overall learning and development strategy for the organization, ensuring alignment with company goals and growth objectives.
• Design, implement, and manage leadership development programs to build strong leaders across all levels, from first-time managers to senior executives.
• Oversee the creation of technical and functional training programs, including product training, compliance, client management, and industry-specific knowledge for roles like sales, operations, and account management.
• Champion career development initiatives that provide colleagues with clear pathways for growth and skill enhancement.
• Foster a culture of continuous learning by driving initiatives such as coaching, mentoring, and self-directed learning opportunities.
• Design and execute programs to identify and develop high-potential colleagues for leadership roles within the organization.
• Collaborate with senior leadership to ensure alignment of development programs with the company’s succession planning efforts.
• Create executive coaching programs and leadership assessments to cultivate key leadership behaviors and competencies.
• Partner with external vendors or consultants to enhance leadership offerings when necessary.
• Lead the adoption and use of learning technologies to deliver scalable, engaging, and measurable learning experiences.
• Drive innovation in training delivery, utilizing a blend of online, in-person, and hybrid learning approaches to meet the diverse needs of the workforce.
• Measure and analyze the impact of learning initiatives on colleague performance, engagement, and business outcomes, adjusting as needed to ensure maximum effectiveness.
• Partner with business leaders to identify learning and development needs and tailor programs that are function-specific, addressing both technical skills and soft skills.
• Work closely with HR, talent management, operations, and other functions to ensure L&D programs support broader talent initiatives, such as colleague engagement, inclusion, and retention.
• Lead a team of L&D professionals, providing guidance, mentorship, and development to ensure high-quality program delivery and continuous improvement.
• Build relationships with external training providers, universities, and industry organizations to ensure access to cutting-edge content and resources.
• Work closely with HR leadership on talent management initiatives, ensuring that learning programs are integrated with performance management, succession planning, and colleague retention strategies.
• Develop career development frameworks and competency models that support colleague growth across various functions within the brokerage.
• Provide strategic input on succession planning by identifying critical roles and developing bench strength through tailored training programs.
• Provide support for succession planning discussions with key leaders enhancing the transition of leadership.
• Ensure that all learning programs comply with relevant regulatory requirements in the insurance industry.
• Collaborate with compliance teams to design and implement training programs that address regulatory changes and mandates.

Benefits

• Alera Group offers comprehensive benefits to our colleagues, including medical, dental, life and disability insurance, 401k, generous paid time off and much more.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 251-500 employees