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Salary
$120k – $150k per year
Location
In office (Chicago)
Seniority
Senior · 7+ years exp
Visa
No sponsorship (stated in the posting)
Employment
Full-Time

Confirmed on the employer's own hiring board on Nov 8, 2026. First seen by Alion on Oct 26, 2026.

Overview
Company
Impact
Profile match
Argo Group is an underwriter of specialty insurance products in the property and casualty market.

Company

Shared Services

Argo and Farm Family are specialty property and casualty insurance brands whose underwriting companies are wholly-owned subsidiaries of Clearbrook Holdings Inc. Argo and Farm Family partner with agents and brokers to provide insurance solutions that enable businesses to manage risks with confidence.

Job Description

The Learning and Development Specialist will implement and support enterprise-wide learning and development (L&D) programs with a key focus on cohesive and integrated learning processes for a high-performance and inclusive culture. Collaborate with business leaders, HR business partners, subject matter experts and colleagues to identify needs and skills gaps, explore options, design planning and execute effective learning solutions to support the business to achieve strategic goals. This position will manage large-scale projects and deliver engaging, creative, and impactful virtual, in-person, and blended programs to improve individual and organizational performance and development.

This is a 100% in-office position. Candidates must be able to work on-site at a designated company office during standard business hours.

Essential Responsibilities:

  • Establish a strategic roadmap for L&D programs, including manager/leadership development, interpersonal and values-based skills development, and applicable compliance training programs.
  • Lead design, development, implementation, communication and sustainability of centralized learning programs consistent with industry best practices.
  • Build and implement strategies focused on change management and application of the new skills, behaviors or habits.
  • Determine training content for key compliance training needs and ensure the L&D roadmap aligns with state, local, or audit requirements and policies.
  • Assess organizational and functional needs, co-create solutions, and ensure alignment with organizational priorities.
  • Write, edit, and coordinate development of course catalogs, promotional materials, training manuals, reference guides, visuals/handouts, and/or training presentations, as appropriate to the program.
  • Establish and manage a robust succession planning framework for key roles across the organization. Partner with HR Business Partners and Senior Leadership to regularly review and update succession plans to ensure readiness for future leadership transitions.
  • Develop metrics to evaluate and measure program performance, learner outcomes, productivity and satisfaction of learning solutions; leverage data to drive, modify and create future learning offerings.
  • Evaluate program effectiveness utilizing data and gathering feedback and apply insights to improve experiences, outcomes, and business value.
  • Manage end-to-end program delivery from content development to vendor management to budget oversight.
  • Provide support for various strategic and special projects as needed, including performance and talent management initiatives.

Qualifications / Experience Required:

  • Bachelor’s degree with a concentration in Human Resources Management or related field.
  • 7+ years of experience in financial services.
  • Facilitation and training experience.
  • Knowledge of learning needs analysis; instructional/program design, development and evaluation; adult learning concepts and learning methodologies.
  • Project management of multiple and complex HR projects.
  • Experience in implementing leadership and talent management capability review and development initiatives, competency frameworks, performance management, change management, career development, talent management and succession processes.
  • Ability to execute high-impact learning strategies that enhance people and business performance.
  • Results focused; a consultative leadership style that builds high-performing teams across multi-disciplined projects that consistently meet targets and realize organizational benefits.
  • Ability to collaborate with all levels throughout an organization.
  • Excellent interpersonal, organizational and influencing skills and ability to facilitate across all levels of business.
  • Strong written and verbal communication skills.
  • Strong presentation skills.
  • Experience with e-learning systems.
  • Experience with vendor management.
  • Occasional travel required.

Preferred Qualifications:

  • Advanced degree in HR, Organizational Development or Education, a plus.
  • Specialty insurance, a plus.
  • Workday experience a plus
  • Certification(s) in various training programs, a plus.

Chicago Pay Range: $120,000 - $150,000

PLEASE NOTE:

Applicants must be legally authorized to work in the United States. At this time, we are not able to sponsor or assume sponsorship of employment visas.

If you have a disability under the Americans with Disabilities Act or similar state or local law and you wish to discuss potential reasonable accommodations related to applying for employment with us, please contact our Benefits Department at 210-321-8400.

Benefits and Compensation

We offer a competitive compensation package, performance-based incentives, and a comprehensive benefits program-including health, dental, vision, 401(k) with company match, paid time off, and professional development opportunities.

Core Values

At Clearbrook our Core Values are Integrity, Collaboration, Pursuit of Excellence and Forward Thinking. These values reflect who we are today and who we aspire to be - guiding how we work, how we lead and how we succeed.

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