Head of Enrollment (Sales) - College Counseling

Overview

ESM Prep | College MatchPoint is a group of passionate educators dedicated to creating supportive and dynamic learning environments that foster growth and success for our students. Today, we are part of Guidewell Education, a mission-driven company representing a range of successful legacy brands in the education space. Together, our family of brands provides a wide range of support to students, including academic tutoring, college counseling, executive function coaching, and test preparation.

Our Culture & Values

As part of Guidewell Education’s family of Brands, we’re guided by values that shape how we support students and work together as colleagues — we are student-centered, empathetic, expert practitioners, and growth-oriented. These principles show up in every coaching relationship we build and every decision we make. You can read more about how our team lives these values at guidewelleducation.com/about.

Supervisor: VP of College Counseling Sales and Growth

Location: Remote (Residency in CA, CO, or TX strongly preferred; Pacific, Mountain, or Central Time Zones)

Hours: Full-time (40+ hours/week).

Job Summary

The Counseling Sales Manager serves as the "tip of the spear" for ESM Prep | College MatchPoint counseling sales. This is a high-performance sales role designed for a "Proactive Steward" who thrives in the high-stakes, high-emotion world of elite educational services. You are responsible for driving enrollment results by taking high-intent leads and converting them into long-term partnerships through expert consultation and meticulous pipeline management. While the marketing team generates the initial interest, you are the closer—responsible for articulating a premium value proposition to sophisticated families, identifying organic referral opportunities, and ensuring our brand remains the primary trusted advisor for families navigating their students' futures.

Duties/Expectations

• Facilitate the daily intake and sales process, conducting high-touch consultations that move families from inquiry to enrollment through a deep understanding of their needs and our specific service philosophy.
• Manage the prospective family pipeline with rigor, maintaining consistent, empathetic, and persistent follow-up to move opportunities through the enrollment funnel.
• Drive organic growth by reviewing current client rosters and "trailing sibling" data; proactively identify opportunities for holistic family support and long-term engagement.
• Serve as the primary architect of the client-counselor match: quickly master our roster of counselors to ensure every incoming family is paired with the practitioner best suited to their student’s goals, personality, and location.
• Collaborate with counselor managers to monitor team capacity, ensuring that sales commitments align with operational reality and maintaining a feedback loop on market trends and family needs.

About You

• You are a Master Closer: You view sales as a service and understand that a child’s future is a high-stakes investment that requires a confident, high-integrity closing style.
• You are a Quick Study: You don’t need to be a counselor, but you do need to be a "subject matter sponge." You have the intellectual curiosity to master the nuances of the US admissions landscape and speak with authority to demanding clients within weeks.
• You are Proactive, Not Reactive: You do not wait for the phone to ring. You view a quiet calendar as an opportunity to mine the existing ecosystem for siblings, renewals, or referral partnerships.
• You Navigate Luxury with Ease: You are comfortable and confident speaking with high-net-worth families. You understand the "white-glove" touch required to build trust with sophisticated, demanding stakeholders.

Requirements

• Sales Excellence: 5+ years of a proven track record in high-ticket sales, luxury services, or enrollment management. 
• Consultative Value Articulation: Exceptional ability to navigate complex conversations regarding cost and value, confidently guiding families to understand why an investment in ESM | CMP is the right strategic decision.
• Regional Market Presence: While this is a remote role, you ideally reside in the Western or Southwestern US (CA, CO, TX, etc.). You must be willing to learn the Texas educational market and be available for occasional travel to Austin for market immersion and team alignment.
• Pipeline Management: Proficiency in CRM tools to manage a complex, multi-touch sales cycle without letting leads go cold.
• Adaptable Expertise: A demonstrated ability to quickly achieve mastery in a new, technical industry. Experience in EdTech or premium educational services (test prep, tutoring) is a strong plus, but not a requirement.
• Public Presence: Exceptional presence for family-facing webinars and community presentations; you can simplify complex concepts into a compelling, persuasive narrative.
• Tool Belt: Proficiency in Google Suite, Notion, Zoom, and modern sales communication tools.

Compensation & Benefits

• Compensation: annual “on track” earnings of $120,000 - 130,000 through a combination of salary, sales commission, and bonus opportunities.

• Benefits:
  • Company-sponsored medical, dental, vision, and life insurance
  • Generous holidays and paid-time-off
  • 401-k with company match after one year with the company
  • Employee discount on services

Diversity and Inclusion:

We believe that diversity and inclusion enrich education and drive success. We are committed to ensuring that all people who interact with Guidewell Education--parents, students, staff, contractors, partners, vendors--are respected and valued holistically. We are committed to attracting and retaining students and staff from diverse cultures, backgrounds, and experiences because we believe that diversity fuels innovation and education to new heights.

The Legal Stuff:

Applicants will be considered for the position on the basis of their qualifications and ability to perform the job for which they are applying. Guidewell Education does not discriminate on the basis of race, color, genetics, religion, gender, gender identity or expression, sexual orientation, national origin, disability, age, or status as a special disabled or other veteran covered by the Vietnam Era Veterans Readjustment Act of 1974, as amended.

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