Remote Underwriting Training Program Jobs in Wisconsin

Cayenta, a division of Harris; is seeking a Professional Services Trainer who will join our Professional Services team to support customer implementations, software adoption, and user readiness initiatives across utility and local government customers.

Are you passionate about helping customers successfully adopt new technology?

Do you enjoy facilitating training, building relationships, and helping organizations navigate change during software implementations?

Then this is the role for you.

This remote role welcomes candidates anywhere in Canada and the US. Travel is required as needed, approximately 25-50%. Candidates must hold a current, valid passport and be legally eligible to travel internationally. This includes either passport based visa exemption or possession of any required travel visas for entry into Canada, the United States, and the Caribbean.

Salary:

70K-80K

AI & Innovation Mindset

We are committed to leveraging emerging technologies to improve how we work, serve our customers, and drive business outcomes. The successful candidate will demonstrate curiosity and a willingness to actively adopt and leverage AI tools to improve workflows, solve problems, and increase efficiency. Candidates should be comfortable using AI enabled technologies, including copilots, chat based AI assistants, and automation tools, as part of their everyday work while maintaining appropriate judgment, security, and compliance standards.

What your impact will be:

• Deliver engaging instructor-led, virtual, and onsite training sessions for customers implementing Cayenta software solutions.
• Facilitate role-based training programs for end users, administrators, supervisors, and system champions.
• Lead train-the-trainer sessions to prepare customer resources to support ongoing knowledge transfer within their organizations.
• Partner with Project Managers, Consultants, and implementation teams to develop customer training schedules and readiness plans aligned with project timelines.
• Serve as the training lead throughout implementation projects, ensuring customers are prepared for system adoption and go-live activities.
• Support organizational change and user adoption efforts during implementations, upgrades, and major process changes.
• Deliver refresher training and post-go-live learning support as customers transition into production environments.
• Coordinate training logistics, schedules, attendee management, and session communications as part of implementation delivery.
• Gather participant feedback and training metrics to continuously improve the customer learning experience.
• Collaborate with Product Management, Development, Support, and Consulting teams to identify knowledge gaps and customer training opportunities.
• Maintain and update existing training materials, job aids, and user documentation to reflect product enhancements and customer requirements.
• Provide recommendations and best practices to improve training delivery and customer adoption outcomes.
• Travel to customer locations to deliver onsite training, support implementation activities, and facilitate user adoption initiatives as required.
• Support customers during critical implementation milestones, including testing, go-live preparation, and post-go-live stabilization activities.

What we are looking for:

• Experience delivering software or systems training in a customer-facing environment.
• Experience within Professional Services, software implementation, ERP consulting, Customer Success, or SaaS organizations.
• Demonstrated experience facilitating instructor-led classroom, virtual, and webinar-based training.
• Excellent presentation, facilitation, and communication skills.
• Ability to explain technical concepts and business processes in a clear and practical manner.
• Strong customer relationship and stakeholder management skills.
• Ability to adapt delivery style to technical and non-technical audiences.
• Ability to manage multiple customer projects and priorities simultaneously.
• Strong organizational and project coordination skills.
• Proficiency with Microsoft 365 applications including Teams, PowerPoint, Word, Excel, and Outlook.
• Experience using webinar platforms and virtual training technologies.
• Experience with utility billing, customer information systems, ERP software, municipal software, or local government operations is considered an asset.
• Comfortable traveling to customer sites throughout North America to support training delivery and implementation activities.
• Ability and willingness to travel up to 25-50% based on customer and project requirements.

What would make you stand out:

• Experience supporting enterprise software implementations.
• Experience delivering train-the-trainer programs.
• Familiarity with change management and user adoption practices.
• Experience working with utility, municipal, or public sector customers.
• Experience working with geographically dispersed customers and delivering both onsite and virtual training programs.
• Willingness and ability to travel throughout North America as required to support customer implementations and training delivery.

What we can offer:

• 3 weeks' vacation and 5 personal days
• Comprehensive Medical, Dental, and Vision benefits starting from your first day of employment
• Employee stock ownership and RRSP/401k matching programs
• Lifestyle rewards
• Remote work and more!

About Cayenta:

Cayenta is a leading provider of enterprise resource management solutions in the local government, utility and financial industries. Cayenta's products, services and customer relationships provide the foundation for continued innovation and growth.

About Harris:

Harris is a leading provider of mission critical software to the public sector in North America. As a wholly owned subsidiary of Constellation Software Inc. ("CSI", symbol CSU on the TSX), Harris has become the cornerstone for CSI's investment in utility, local government, school districts, public safety, and healthcare software verticals. Our success has been realized through investments in our proprietary software and market expertise. This focus, combined with acquiring businesses that build upon or complement our offerings, has helped drive our success. Harris will continue to growth through reinvestment - both in the people and products that we offer and making investments in acquiring new businesses.

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