Enrollment Advisor & MTSS Specialist (Remote)

About Williamsburg Learning At Williamsburg Learning (WL), we aim to prepare promising students for meaningful lives as principled leaders. We partner with schools like Williamsburg Academy, Leadership Academy of Utah, and Williamsburg Academy of Colorado to deliver transformational learning experiences that spark curiosity, growth, and purpose. We live by our values—Growth, Right Action, and a Culture of Belonging. We believe work should be meaningful and fun. Our team is authentic, connected, and committed to doing the right thing for each other and the students we serve. To support our people, WL offers 100% paid health premiums for full-time employees (75% for families), a 100% 401(k) match up to 4%, PTO, plus many more perks! If our mission and culture resonate with you, we would love to have you on our team! Position Summary Note: This position is a dual role in which you would work from approximately April through August as an Enrollment Advisor, and from September through March as an MTSS Specialist. See below for a full description of both. The Enrollment Advisor is a vital member of the Admissions Department and the first point of contact for prospective families at the Williamsburg Family of Schools. Successful Enrollment Advisors use a unique set of sales, communication, writing, and organizational skills to help families determine if our program is the right fit and start the school year on a high note. The MTSS Specialist plays a crucial role within the Academics Department, providing extra layers of support to students in the Williamsburg program. A successful MTSS Specialist uses strong communication, problem-solving, and organizational skills to collaborate closely with families and mentors and build tailored plans to help students succeed. Essential Duties As an Enrollment Advisor: Conduct Enrollment Consultations with prospective parents, explain the benefits of our program, answer questions, and guide parents through our enrollment options. Assist parents with course selection, provide essential onboarding resources, and address pre-semester questions to help new students have a strong start. Keep track of parent information and interactions in HubSpot, set and complete follow-up tasks, and report on performance metrics. Stay informed about the Williamsburg curriculum, policies, and other updates to provide accurate, insightful guidance to families. Document new information and procedures in our team knowledge base, helping your teammates stay up-to-date. Share feedback from parents, collaborate with colleagues, and recommend process improvements to continually refine the enrollment process. Stay flexible and ready to adapt to evolving needs and priorities. As an MTSS Specialist: Support students who need extra help by creating personalized intervention plans through collaboration with families, mentors, and colleagues. Track and keep parents and mentors updated on student progress and share insights when a student may need additional services. Run student support labs by inviting at-risk students, keeping track of attendance and assignments, and offering tips to help them stay on track. Help mentors put effective classroom support strategies in place and attend training to stay up-to-date on implementation tips. Coach students through academic challenges by assisting with assignments, providing tutoring in specific subjects, and teaching time management and study skills. Join team meetings to report on and discuss student progress, share ideas, and set professional growth goals. Continually research and suggest new ways to better support students. Minimum Qualifications Two years of work experience in a conversational sales setting, and/or Two years experience in a school setting where you directly engaged with parents and students (i.e. admissions, tutoring, teaching, as a TA, or similar) Excellent interpersonal, organizational, and communication skills Ability to work independently and manage your own schedule, and willingness to alternate between different types of work throughout the year Preferred Qualifications Associate’s degree or higher Proficiency in HubSpot or similar CRM; HubSpot certifications are ideal Ability to collaborate with a team to build toward a shared vision Ability to empathize with and meet the needs of diverse students and families Quick learner with various technology systems and processes Required Equipment (You Provide) A computer with webcam (no older than two years) Headset or headphones with echo-canceling mic High-speed internet service – the faster the better (we recommend 5 Mbps or more) Compensation & Schedule Compensation: $58,656 annual salary Start date: ASAP Schedule: 40 hours per week, Monday through Friday Benefits After meeting the eligibility requirements, benefits are available, including Health, 401(k) Retirement, Paid Holidays, and Paid Time Off. Williamsburg Learning is an Equal Opportunity Employer