Training & Enablement Specialist

Ategrity Specialty Insurance Company; United States; On-site; USD 110,000 - 150,000; Full time

Benefits offered by this job

Competitive salary

Benefits package

401(k) match

Paid time off

Career growth

Job summary

Ategrity Specialty Insurance Company is seeking a Senior Learning & Readiness Specialist to design, deliver, and continuously improve the training strategy for AtegrityOne and future platform enhancements.

The role partners with Product, Underwriting, Operations, Distribution, Technology, Business Readiness, and Partner Support to ensure effective learner readiness and post‑launch improvements.

Qualifications

• 5+ years designing and delivering enterprise software training.
• Experience with instructional design methodologies.
• Experience supporting large-scale technology implementations.
• Strong presentation and facilitation skills.
• Excellent technical writing and documentation skills.
• Ability to work across business and technology organizations.

Responsibilities

• Own the end-to-end training strategy for AtegrityOne and future platform enhancements.
• Develop role-based curricula for Operations, Service Delivery, Distribution, UW, Finance and Partners.
• Create instructor-led training, virtual classes, recorded modules, eLearning, simulations, job aids, guides, and assessments.
• Lead Train-the-Trainer sessions and certify internal trainers.
• Partner with PMO and Business Readiness to align training with deployments.
• Support HyperCare by updating FAQs and materials after releases.
• Maintain all training materials through release cycles and version control.
• Develop knowledge articles and searchable content for Support and HyperCare.
• Build SOPs, process maps, call flows, and playbooks.
• Measure training effectiveness through surveys and metrics.

Skills

Instructional design

Enterprise software training

Large-scale tech implementations

Presentation skills

Technical writing

Cross-functional collaboration

Tools

LMS

SharePoint

Job description

Company Overview: Ategrity Specialty Insurance Company specializes in property and casualty insurance, with a strong emphasis on the excess and surplus (“E&S”) lines market, partnering with brokers and wholesale agents throughout the U.S. to provide insurance solutions for small and medium-sized enterprises (SMEs). Our aim is to establish ourselves as the premier E&S carrier, leveraging robust technical underwriting, intelligent operational efficiencies, sound risk management, and intensive specialization to excel in the marketplace. We are firmly on track to achieve this success.

Ategrity is a proactive organization, driven by data obsession, and guided by a culture of innovation. Our team is comprised of individuals who take action with unwavering determination and conviction to establish our “right to win” in the SME space. Ategrity’s underwriting strategy focused on becoming a leader in specific segments of E&S through efficient operationalization of technical underwriting practices and a strong value proposition.

Position Summary

This role is responsible for designing, developing, delivering, and continuously improving the learning and readiness strategy supporting AtegrityOne. The specialist partners with Product, Underwriting, Operations, Distribution, Technology, Business Readiness, and Partner Support to ensure employees and external partners are prepared for each release. The position owns curriculum development, train-the-trainer programs, operational documentation, knowledge management, rollout readiness, HyperCare enablement, and post-launch learning improvements.

Core Responsibilities

• Own the end-to-end training strategy for AtegrityOne and future platform enhancements.
• Develop role-based curricula for Operations, Service Delivery, Distribution, UW, Finance and Partners.
• Create instructor-led training, virtual classes, recorded modules, eLearning, simulations, job aids, quick reference guides, FAQs, facilitator guides, participant workbooks, and other training channels, and assessments.
• Lead Train-the-Trainer sessions and certify internal trainers before rollout.
• Partner with Business Readiness and PMO to align training with deployment milestones and phased rollouts.
• Support pilot programs by observing users, documenting gaps, and updating materials before production launch.
• Maintain all learning documentation through release cycles and version control.
• Develop knowledge articles and searchable content for Partner Support and HyperCare teams.
• Build operational documentation including SOPs, process maps, call flows, escalation guides, decision trees, work instructions, and support playbooks.
• Leverage AI tools as appropriate
• Partner with SMEs to document manual workarounds, post-issuance activities, API scenarios, known issues, and production support procedures.
• Support HyperCare by identifying recurring questions, updating FAQs, and recommending improvements to training content.
• Identify and raise gaps, user enhancements to the PMO team for prioritization
• Measure training effectiveness through surveys, knowledge assessments, adoption metrics, support trends, and call dispositions.
• Present readiness status and training progress to leadership.
• Establish and maintain learning governance standards, templates, and quality controls across all training deliverables

Day-to-Day Activities

• Attend project working sessions and sprint reviews.
• Translate business requirements into learning content.
• Update training decks as functionality changes.
• Coordinate classroom schedules and communications.
• Conduct live demonstrations and office hours.
• Maintain SharePoint or LMS learning libraries.
• Review production defects for training impacts.
• Partner with communications on rollout messaging.Coordinate and monitor external training initiatives to ensure consistency

Required Qualifications

• 5+ years of designing and delivering enterprise software training.
• Experience with instructional design methodologies.
• Experience supporting large-scale technology implementations.
• Strong presentation and facilitation skills.
• Excellent technical writing and documentation skills.
• Ability to work across business and technology organizations.

Preferred Qualifications

• Commercial insurance experience.
• Experience with policy administration platforms.
• Business Readiness or Organizational Change Management.
• Learning Management Systems (LMS)
• HyperCare or post-implementation support experience.

Success Measures

• 100% of required training delivered before each rollout phase.
• Training materials updated within agreed SLAs following functional changes.
• Reduction in Tier 1 support questions through effective education.
• Positive learner satisfaction scores.
• Improved user adoption and operational readiness.
• Accurate operational documentation maintained for every release.
• Train-the-Trainer Program
• Participant Guides
• Quick Reference Guides
• Knowledge Articles
• FAQs
• Support Playbooks
• HyperCare Documentation
• Process Maps
• Standard Operating Procedures
• Release Readiness Checklists
• Competitive salary commensurate with experience
• Comprehensive benefits package including medical, dental, and vision coverage
• 401(k) retirement savings plan with employer match
• Paid time off and company holidays
• Collaborative and inclusive work environment with opportunities for career growth and advancement

Ategrity Specialty Insurance Company is an equal opportunity employer and values diversity in the workplace. We encourage candidates from all backgrounds to apply.