Head of Training

The Position

We're looking for a strategic and hands-on Head of Training to lead our training team and elevate how we support schools across their entire journey with jmc. This role owns the vision, strategy, and execution of training programs that help educators and administrators gain confidence and proficiency with jmc—from new school onboarding through ongoing feature adoption and advanced skill development.

You'll lead a team of training specialists and work closely with Client Services, Product, Marketing, and Technical Support to ensure our training programs are high-impact, scalable, and aligned with how schools actually work. This is an opportunity to shape the training experience for 1,000+ schools and build programs that directly contribute to customer success, retention, and growth.

This is a player/coach role in the near term, with an opportunity to evolve into a more strategic leadership position as programs and team capacity scale.

Qualifications

• 7–10+ years of experience in training, professional development, or learning & development roles, with at least 3–5 years in a leadership capacity
• Proven ability to design, implement, and scale training programs across multiple formats (webinars, on-site workshops, self-paced learning, 1:1 coaching)
• Strong strategic thinking and planning skills with demonstrated ability to translate business goals into actionable training initiatives
• Experience managing and developing training teams; comfortable coaching, delegating, and holding team members accountable
• Deep understanding of adult learning principles and instructional design best practices
• Excellent communication and presentation skills; confident leading sessions for diverse audiences
• Experience with K–12 education, SIS platforms, or EdTech strongly preferred
• Proficiency with training platforms (webinar tools, LMS, Help Centers) and ability to evaluate and implement new technologies
• Comfortable with data: can define success metrics, track performance, and use insights to improve programs
• Self-directed, organized, and results-oriented; able to manage multiple priorities and adapt quickly to changing needs
• Experience leading change initiatives or large-scale program rollouts in a customer-facing environment

Responsibilities

Training Strategy & Program Leadership

• Own the overall training strategy and roadmap, ensuring alignment with company goals, customer needs, and product evolution
• Design and implement comprehensive training programs that support the full customer lifecycle: new school onboarding (NSO), feature adoption, ongoing education, and advanced proficiency development
• Lead year-round training initiatives including monthly feature webinars, weekly office hours, state reporting readiness training, and regional workshops
• Partner with Product and Marketing to ensure timely training support for new features, product launches, and strategic campaigns (e.g., Differentiators Campaign, portal modernization)
• Continuously assess and improve training effectiveness based on customer feedback, support ticket trends, and adoption metrics
• Evaluate emerging training technologies and methodologies to keep programs innovative and efficient

Team Management & Development

• Lead, mentor, and develop a team of training specialists, providing clear direction, feedback, and growth opportunities
• Establish team workflows, standards, and best practices to ensure consistency and quality across all training deliverables
• Allocate team capacity strategically across competing priorities (scheduled trainings, ad-hoc requests, content development, school visits)
• Foster a collaborative, customer-focused team culture that values continuous improvement and knowledge sharing
• Manage part-time training contractors as needed to handle seasonal demand (e.g., NSO periods)

Training Delivery & Execution

• Deliver high-impact training sessions across formats: webinars, on-site workshops, virtual 1:1 sessions, and conference presentations
• Personally deliver select high-impact or strategic training sessions while ensuring the broader training calendar is owned and executed by the team
• Ensure training content is clear, engaging, role-based, and aligned with real-world school workflows
• Develop and maintain training materials including presentations, guides, videos, job aids, and Help Center articles
• Coordinate closely with Client Services Specialists on site visits, check-in calls, and proactive customer touchpoints to reinforce training and drive adoption
• Support new school onboarding by leading training sessions, creating onboarding resources, and ensuring customers are confident and successful on Day 1

Cross-Functional Collaboration

• Partner with Product and Development teams to stay ahead of product updates, provide user feedback, and inform feature prioritization
• Work with Marketing to align training programs with campaign messaging, customer communications, and content creation
• Collaborate with Technical Support to identify common user challenges, reduce support tickets through proactive training, and improve Help Center resources
• Provide training insights and customer feedback to leadership to inform product roadmap, customer success initiatives, and strategic planning

Metrics, Reporting & Continuous Improvement

• Define and track key training metrics: attendance rates, completion rates, user satisfaction scores, feature adoption, support ticket reduction, and customer confidence levels
• Analyze training performance data and customer feedback to identify gaps, trends, and opportunities for improvement
• Report regularly to leadership on training outcomes, team performance, and strategic recommendations
• Stay current on K–12 trends, SIS industry developments, and best practices in training and customer education

Who You Are

• A strategic thinker who can see the big picture while also rolling up your sleeves to execute and deliver excellent training experiences
• A confident leader who empowers your team, sets clear expectations, and holds people accountable with empathy and respect
• Passionate about education and committed to helping schools succeed through better technology adoption
• Highly organized and able to manage competing priorities without losing sight of quality or customer impact
• A strong communicator who can present to large groups, facilitate tough conversations, and build trust with stakeholders at all levels
• Customer-obsessed: you genuinely care about user success and are motivated by seeing schools thrive with jmc
• Comfortable operating in a growing, evolving company where you'll need to build, iterate, and adapt as needs change

Success in This Role Looks Like

• Training programs are strategically aligned with business goals and consistently drive measurable improvements in customer confidence, feature adoption, and retention
• The training team operates efficiently and collaboratively, with clear workflows, high morale, and strong performance
• New schools complete onboarding with high satisfaction scores (90%+) and feel fully prepared to use jmc on Day 1
• Support tickets related to "how-to" questions decrease as proactive training and Help Center resources improve
• Training attendance and engagement metrics meet or exceed targets; customers actively participate in ongoing learning opportunities
• Cross-functional partners (Product, Marketing, Client Services, Support) view Training as a trusted, strategic partner
• You're recognized as a thought leader internally and externally, representing jmc's commitment to customer success

Location

This position is remote (jmc, Inc. is based in Lake City, Minnesota).

To Apply

Send your resume and a brief letter of introduction to hr@jmcinc.com‍