Remote Training Specialist (Wisconsin)

Xello is looking for a Training Specialist (Wisconsin)

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Who are you?

You are an enthusiastic, mission-driven educator-at-heart who loves empowering others. You're an energetic communicator with exceptional presentation skills and a passion for helping schools create meaningful future-readiness experiences for every student. You have a strong understanding of Wisconsin’s K–12 landscape and are excited to support districts as they strengthen and refine their Academic and Career Planning (ACP) process.

You enjoy translating complex policy and statewide initiatives into clear, relevant, and actionable learning experiences. You're a strong collaborator, highly organized, and comfortable delivering engaging training in both virtual and in-person environments. You’re deeply attuned to the voice of the customer, gathering real-world insights to help educators overcome barriers and amplify best practices. Above all, you are committed to educational equity and to helping educators maximize their impact on students.

What you’ll do…

Training & Technical Assistance

• Work closely with DPI’s Academic & Career Planning Consultant to empower educators to deliver strong ACP experiences for all students.
• Create and deliver synchronous and asynchronous training that integrates the ACP process and the Xello platform.
• Facilitate online, hybrid, and in-person professional learning for administrators, teachers, counselors, data coordinators, and communications staff.
• Develop and maintain ACP professional development materials, such as training modules, guides, and videos.
• Create a student- and family-friendly guide to help Wisconsinites understand available career readiness programs and pathways.
• Support school staff in using Xello platform data to take targeted action and boost student engagement.

Collaboration & Support

• Partner with district leaders, CESAs, and Wisconsin stakeholders to strengthen ACP implementation and drive adoption of best practices.
• Participate in planning and strategy sessions with schools to support continuous improvement aligned with DPI priorities.
• Collaborate with Xello’s cross-functional teams, including Success, Onboarding, and Training to ensure Wisconsin districts fully adopt and maximize Xello.
• Represent Xello and Wisconsin’s ACP initiatives at regional events, conferences, and statewide convenings.
• Participate in meetings, site visits, and other events to build awareness of Xello and develop relationships with ACP stakeholders across the state.
• Serve as a field researcher, gathering authentic user stories, understanding barriers, and identifying best practices to share with internal teams.

Evaluation, Research & Best Practices

• Identify and share model ACP practices that demonstrate positive impact on student outcomes (attendance, graduation, dual enrollment, work-based learning engagement, etc.).
• Use data to inform recommendations, refine training materials, and support statewide improvement efforts.
• Stay current on Xello product updates, Wisconsin E4E/ACP requirements, career pathways initiatives, and dual enrollment changes, and incorporate these updates into training and support.

What we’re looking for…

• Deep understanding of Wisconsin Education for Employment (E4E) and ACP statutory requirements
• Familiarity with Wisconsin Career Readiness Standards and regional K–12 career pathway development
• Knowledge of Wisconsin’s dual enrollment programs (ECCP and Start College Now)
• High competency in analyzing educational data to evaluate ACP practices and student outcomes
• Experience implementing ACP or similar future-readiness initiatives in K–12 settings
• Experience and comfort with CRM systems (e.g. Salesforce) and Google Suite
• Experience working with SaaS or the education technology industry (nice to have)
• Driver’s license required
• Ability and willingness to travel across Wisconsin, with occasional out-of-state travel

The compensation for this role offers an OTE ranging from $65,000 to $75,000 USD base with a $5,000 USD incentive. The final offer will be determined based on the candidate's experience and expertise, as assessed during the interview process. The start date for this role is flexible.

We’re Xello - Join us!

We are Xello (CASCAID in the UK), the leading developer of future readiness programs in North America and the UK and soon the world! Our mission is to help anyone, anywhere in the world to create a successful future through self-knowledge, exploration, and planning.

We believe that by bringing our best selves to our work and collaborating with one another, we can change the world. We are a very diverse group of individuals who work hard, laugh often and share in each other’s lives. We are an inclusive, equal opportunity employer.

Embracing agile practices, an innovative mindset, and keeping our users at the heart of what we do, are just a few of the keys to our success.

In addition to working with leading technologies, we are committed to continuous learning and growth through internal/external training and mentoring, which includes a PD budget for every employee.

For our Canadian based staff, we also offer:

• Flexible work arrangements including hybrid and remote


• 4 weeks of vacation


• Employer-paid health and dental benefits


• 4-month top-up for parental leave


• Group RRSP with 3% matching

For our US based staff, we also offer:

• Remote work environment


• 4 weeks of vacation


• 80% employer-paid health benefits


• 4-month top-up for parental leave


• 401(k) with 3% matching

For our UK based staff, we also offer:

• Remote work environment


• 28 days annual leave (inc. 3 days at Christmas) + bank holidays. With additional annual leave days added to reward long service

Like what you hear? Apply Now!