Guidewire Master Trainer

Role: Guidewire Master Trainer

Location: New Berlin, NY

Type: Contract

Job description:

In this role, you will act as the Master Trainer for the Guidewire end-user training program, delivering instructor-led classroom training to the client’s business users at their US office. You will own delivery on the ground — running full-day sessions across Guidewire ClaimCenter and PolicyCenter, fielding live Guidewire questions from users who are seeing the tool for the first time, and adjusting pace and depth to the room in front of you. The curriculum, facilitator decks, quick reference guides and simulations are already built by the program team; your job is to bring them to life in the classroom. This is a short-term contract, individual contributor role — you will deliver independently, with no co-facilitator onsite.

Responsibilities

· Deliver instructor-led (ILT) end-user training onsite at the client location over a continuous two-week window at the end of October/ beginning of Nov, covering Guidewire ClaimCenter, Digital Portal (for Agents) and PolicyCenter.

· Facilitate full-day classroom sessions for mixed business audiences — claims adjusters, underwriters, and operations staff — the majority of whom will be using Guidewire for the first time.

· Run each session end to end and independently: room and environment setup, session opening, live system demonstrations, guided hands-on exercises, knowledge checks, and wrap-up.

· Answer live questions on Guidewire navigation, screens, workflows and configuration, and connect them back to day-to-day insurance process — FNOL, claim assignment and

adjudication, reserves, payments, submission, quote, bind, issue, endorsements, renewals and cancellations.

· Walk learners through end-to-end business scenarios and use cases across the client’s lines of business, and explain clearly how each process changes versus the legacy policy and claims systems being retired.

· Absorb the approved curriculum, ILT decks, QRGs, web-based training and simulations supplied by the project team, and deliver faithfully against them without redesigning content.

· Rehearse and dry-run every module ahead of delivery; validate the training environment, sample data, user logins and system readiness before each session.

· Track attendance and participation, capture questions that cannot be resolved in the room, and log content gaps, data issues and system defects for the program team on a daily basis.

· Provide daily delivery feedback to the Training Lead and PMO on learner readiness, adoption risks, and individuals or teams needing follow-up reinforcement.

· Provide at-elbow support and floor-walking reinforcement between formal sessions where scheduled.

· Represent the program professionally in front of client business users and leadership throughout the onsite engagement.

Qualifications Minimum qualifications

· Bachelor’s degree or equivalent practical experience.

· Based in the United States and able to travel to the client site for a continuous two-week onsite engagement at the end of October. Candidates based outside the US will be considered only where they can commit to the full two-week onsite window and hold valid work authorization and travel documentation for the US.

· Deep, hands-on Guidewire expertise — end-to-end command of ClaimCenter, Digital Portal (for Agents) and PolicyCenter functionality, screens, workflows, roles and permissions, and configuration behavior, at a level that allows unscripted questions to be answered with confidence.

· Strong P&C insurance domain knowledge across personal and commercial lines of business, with the ability to explain Guidewire process in the language of underwriters, adjusters and operations staff rather than in system terms.

· Demonstrated experience delivering instructor-led end-user training on Guidewire to business audiences (not developer or technical bootcamp training), ideally in the run-up to a go-live.

· Clear, neutral US English delivery. The audience is US-based business users and the trainer must be immediately and comfortably understood across consecutive full days in the classroom.

· Proven ability to run training fully independently as an individual contributor — owning preparation, delivery, logistics and issue escalation without day-to-day supervision.

· Confidence handling a live room: managing challenge and skepticism from experienced insurance professionals, improvising when the system or data does not behave as expected, and keeping a session on track.

· Professional presence and the stamina to deliver back-to-back full-day sessions for two weeks.

Preferred qualifications

· Guidewire certification — ClaimCenter and/or PolicyCenter (Associate level or above), or Guidewire Cloud certification.

· Prior experience on a Guidewire InsuranceSuite go-live at a US regional or mutual P&C carrier.

· Experience training users migrating from a legacy policy or claims administration platform to Guidewire.

· Train-the-trainer, super-user or change-champion enablement experience.

· Familiarity with WhatFix or comparable digital adoption platforms, and with blended curricula combining WBT, ILT, QRGs and simulations.

· Working knowledge of Guidewire Jutro / digital portals.

· Formal facilitation credentials (e.g. ATD / CPTD).