Job Details

Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers.

Orchid Insurance, an Arrowhead Intermediaries company is seeking a Learning & Development Manager to join our growing office in eitherTampa or Vero Beach, FL.

The Learning & Development Manager is responsible for building and scaling high-quality learning programs that support operational excellence across the organization. This role focuses on understanding operational workflows, systems, and business processes, and converting them into targeted learning solutions that improve accuracy, efficiency, and teammate performance. Working in a highly collaborative environment, the L&D Manager designs, delivers, and evaluates learning programs that strengthen capability within Operations teams including underwriting support, service operations, production support, specialty teams, and related business functions.

This role includes program design, instructional development, facilitation, LMS coordination, measurement and analytics, vendor management, and continuous improvement of learning processes.

How You Will Contribute:

The Learning & Development Manager:

• Designs, develops, and implements learning programs, job aids, and performance support tools that support operational workflows, systems training, and business processes.
• Performs needs assessments in partnership with operational leaders to identify knowledge gaps, skill gaps, or process gaps that impact performance or customer experience.
• Translates complex operational content into structured learning experiences including curricula, documentation, guides, simulations, and reference materials.
• Partners with SMEs, Process Owners, QA/Audit, and Operations leadership to define learning requirements and validate content accuracy.
• Coordinates with LMS administrators and external vendors to ensure content distribution, accessibility, tracking, and reporting.
• Monitors feedback, evaluates effectiveness, and measures learning outcomes using performance, quality, and operational metrics.
• Continuously optimizes learning processes and assets to reduce rework, improve time-to-competency, and enhance user experience.
• Conducts research and benchmarking on learning trends, learning technologies, and workflow enablement tools.
• Supports audits, compliance updates, rollout communications, change management, and documentation related to new products, system releases, and operational changes.
• Leads small-to-medium scale L&D projects and contributes to cross-functional initiatives that improve operational training maturity.
• Prepares written and verbal summaries, training plans, and recommendations for senior stakeholders.

Skills and Experience to Be Successful:

Requirements:

• Ability to design and develop training content, curricula, job aids, and system training materials.
• Facilitate engaging learning sessions both virtually and in person.
• Work with SMEs to gather requirements and validate technical accuracy.
• Ability with project planning, scheduling, prioritization, and stakeholder communication.
• Use data to assess learning effectiveness and inform improvements.
• Have strong written communication, documentation, and instructional writing.
• Build learning measurement strategies and feedback loops.
• Advanced proficiency in PowerPoint, Word, Excel, and process documentation tools (e.g., Visio, Lucidchart, Miro, etc.).
• Attention to detail, follow-through, and ability to deliver with high quality.
• Learning & development practices, instructional design models, and adult learning theory.
• Operational training methods include SOP development, workflow mapping, systems training, and performance support tools.
• Business process improvement methodologies and continuous improvement concepts.
• Data-driven performance measurement and training impact analysis.
• LMS platforms, learning technologies, and digital enablement tools.
• Strong business acumen with the capacity to quickly grasp organizational operations and industry nuances to inform learning strategy and content development.

Optional Skills:

• Four plus years of experience in Learning & Development, Instructional Design, Operational Training, or similar function.
• Prior Property & Casualty insurance experience
• Experience supporting Operations, shared services, underwriting, service center, financial services, or other process-driven environments preferred.
• Translate operational complexities into structured, consumable learning.
• Collaborate effectively with cross-functional teams and SMEs at all levels.
• Manage multiple projects concurrently in a fast-moving environment.
• Create clarity and structure where process maturity is evolving or ambiguous.
• Think analytically, connecting training outcomes to performance results.
• Problem-solve and make informed recommendations when requirements are not fully defined.
• Work independently while maintaining strong stakeholder engagement.
• Maintain a learner-centric approach while supporting business priorities.

Teammate Benefits & Total Well-Being

We go beyond standard benefits, focusing on the total well-being of our teammates, including:

• Health Benefits: Medical/Rx, Dental, Vision, Life Insurance, Disability Insurance
• Financial Benefits: ESPP; 401k; Student Loan Assistance; Tuition Reimbursement
• Mental Health & Wellness: Free Mental Health & Enhanced Advocacy Services
• Beyond Benefits: Paid Time Off, Holidays, Preferred Partner Discounts and more.

Not reflective of all benefits. Enrollment waiting periods or eligibility criteria may apply to certain benefits. Benefit details and offerings may vary for subsidiary entities or in specific geographic locations.

The Power To Be Yourself

As an Equal Opportunity Employer, we are committed to fostering an inclusive environment comprised of people from all backgrounds, with a variety of experiences and perspectives, guided by our Diversity, Inclusion & Belonging (DIB) motto, "The Power to Be Yourself".