About Keystone 

Keystone is a rapidly growing insurance brokerage platform partnering with independent agencies across the United States. Keystone provides strategic resources, capital investment, and operational support to drive sustainable growth, empowering agencies to maintain their identity while accessing best-in-class tools in finance, HR, sales, and M&A integration. The leadership team brings over a century of combined industry expertise, fostering collaboration, innovation, and long-term value. For more information please visit: https://mykeystone.com/. 

Operations Training Manager

Position Overview:

The Operations Training Manager will play a critical role in enabling transformation – designing, delivering, and optimizing training programs that support agencies through change, ensure successful adoption of new systems, and build ongoing capabilities across our growing organization. This role combines strategic vision, operational excellence, and people leadership. The Training Manager will oversee a team responsible for delivering role‑based and line‑of‑business‑specific training across core workflows, tools, and resources that shape the client experience.

Key Responsibilities:

People Leadership & Team Management

• Lead, coach, and develop a team of trainers focused on role‑based and line‑of‑business workflows, tools, and client‑service processes.
• Ensure consistent, high‑quality training delivery across all programs and channels.
• Set clear priorities, manage capacity, and support professional development within the team.
• Create a culture of continuous improvement, collaboration, and learner‑centric design.

Transformation & Unified Tech Stack Training

• Design and implement the end‑to‑end training strategy that supports the transition of all agencies to the unified technology platform (AMS, CRM, quoting, servicing, workflow tools, etc.).
• Build training programs that integrate operational workflows with technology utilization, so agencies understand both process and system expectations.
• Deliver virtual and in-person training sessions, demos, and reinforcement activities.
• Produce supporting materials including job aids, guides, eLearning, micro-learning, videos, and playbooks.
• Align training delivery to broader change plans, communications, and field readiness strategies.
• Lead ongoing reinforcement training, optimization sessions, and focused workshops to strengthen proficiency.
• Use adoption data and agency performance metrics to identify opportunities for training improvements.
• Act as an internal expert on the unified tech stack and workflow standards.

M&A Conversion Training

• Develop and deliver tailored training programs that support newly acquired agencies through system conversion and process integration.
• Work closely with integration teams to ensure new acquisitions receive clear, consistent, and supportive training experiences.
• Customize training plans based on agency readiness, size, and complexity.

Collaboration & Cross‑Functional Alignment

• Collaborate cross‑functionally with Line of Business Product Owners, the Director of Agency Systems & Solutions, and Field Support Groups to ensure training aligns with workflows, tools, system enhancements, and rollout needs. 
• Serve as a key partner during system implementations, product enhancements, and enterprise solution updates.
• Gather feedback and insights from stakeholders to continuously refine programs.

Workforce Development & Onboarding Programs

• Build and own scalable onboarding programs for: 
  • New-to-industry hires (insurance fundamentals, workflows, systems, servicing standards)
  • Experienced service employees (advanced tools, carrier processes, role-based workflows)
• Establish learning paths for CSRs, account managers, and other non-production agency roles.
• Ensure all learning experiences reflect industry best practices, adult learning principles, and organizational standards.

Required Qualifications:

• 5+ years of experience in training, learning & development, instructional design, or enablement
• Experience in the insurance industry (Property & Casualty and Employee Benefits, Life, and Health)
• Prior leadership experience – managing trainers, facilitators, or instructional designers
• Strong facilitation skills with experience training diverse operational teams
• Proven ability to create learning content across multiple formats
• Experience supporting change, technology rollouts, or workflow redesign
• Excellent communication, project management, and stakeholder management skills
• Willingness to travel approximately 50-75%
• Ability to pass a criminal background check, as permitted by law

Preferred Qualifications:

• Insurance licensing or industry certifications (e.g., P&C License, CISR, CIC)
• Experience with agency management technology, with preferred experience in Applied Epic
• Familiarity with M&A integration or system conversion
• Knowledge of adult learning methodologies and evaluation frameworks

Remote/Hybrid Work Environment: Preference given to candidates in Eastern or Central U.S. time zones

Salary Transparency Statement: In accordance with state and local pay transparency laws, we will provide the applicable salary range upon request to candidates who reside in jurisdictions where such disclosure is required. 

Benefits: 

• Competitive Salary 
• Health Insurance Plans (PPO, HSA, Copay Options) 
• Dental Insurance 
• Vision Insurance 
• Company Paid Disability Insurance 
• Supplemental Insurance including Critical Illness, Accident, Legal, Pet Insurance 
• 401(k) with Safe Harbor Match 
• Paid Time Off
• Paid Holidays 

No Solicitation Notification to Agencies: Please note that Keystone and our Partner Agencies do not accept unsolicited resumes or calls from third-party recruiters or employment agencies. In the absence of a signed Master Service Agreement and approval from HR to submit resumes for a specific requisition, Keystone will not consider or approve payment to any third parties for hires made.