Director of Enrollment

Overview of the Role
As the Director of Enrollment, you are the hands-on operational leader responsible for dramatically improving tour conversion across Guidepost’s U.S. campuses. You build capability in real time, not through static playbooks but by being physically present in schools, modeling world-class parent tours, coaching school leaders and Regional Managers (RMs) side-by-side, and establishing the standards, behaviors, and systems that drive enrollment excellence. 

You will serve as the tip of the spear in building a scalable enrollment model that guilds a sustainable business partner approach where we create the conditions in which regional and school teams deeply understand the field, coach others and intervene when the work requires skill-building or high-touch support. You will report directly to the CEO, US and significant travel alongside SVP People during onboarding to shape a deeply aligned operating model.

This is a do first, build second role and ideal for a leader who changes outcomes by changing behavior in the field. 

Your Key Areas of Focus
Tour Conversion Excellence:

• Personally model high-impact tours and family follow-up practices at priority campuses 

• Observe, coach, and provide immediate feedback to school leaders and RMs to raise conversion quality 

• Build clarity around the signals, standards, and habits that predict conversion success 

Capability Building & Coaching:

• Develop school leaders and RMs through direct modeling, live coaching, and repeated high-touch cycles 

• Establish a clear, behavior-based playbook for tour execution, follow-up, and enrollment discipline 

• Serve as a trusted partner who builds confidence while holding a high bar for performance 
   

Early Model Building (Enrollment Partner Blueprint):

• Begin laying the foundation for a long-term enrollment business partner structure 

• Document what works in the field and translate it into a repeatable, scalable system 

• Inform future design of parent onboarding and retention roles as the model evolves 
   

Cross-Functional Alignment & Impact 

• Partner with School Success and Growth teams to align on prioritization, targets, and interventions 

• Serve as an insight engine — surfacing enrollment blockers, sentiment, and best practices to leadership 

• Help shape the long-term parent lifecycle strategy rooted in firsthand field intelligence 

 

What You Bring

• Track record of driving measurable enrollment, sales, or conversion results in a multi-site setting 

• Deep knowledge and experience effectively selling our Guidepost early childhood programs and enrolling families that stay long-term 

• Experience coaching leaders through live modeling — not only through frameworks or training decks 

• High EQ — able to build trust quickly, read nuance, and deliver direct feedback that sticks 

• Operational rigor and entrepreneurial instinct — comfortable building while moving fast 

• Deep commitment to excellence in the family experience and to Montessori as a mission-driven model 

 

Your Path Forward

In this role, you will help create the foundation for Guidepost’s future enrollment model not only improving conversion now but charting the path toward a fully integrated parent experience function that spans onboarding through retention. As the organization grows, so will your opportunity to shape that broader vision and lead at a national level. We’re looking for someone who leads from the field and changes outcomes by changing what happens in the room.