POSITION DESCRIPTION
We are seeking a Director of Educational Strategy to serve as the ultimate guardian of our service standards. This is a high-impact leadership role for a “practitioner-expert” who understands the nuances of elite college admissions as deeply as the mechanics of high-score test prep. You will bridge our Tutoring and Counseling departments, ensuring that every roadmap we architect is delivered with the precision and white-glove excellence our families expect.
This role requires regular afternoon, evening, and occasional weekend sessions to accommodate student availability across US time zones (particularly Pacific Time). To balance evening student-facing hours, enjoy significant autonomy and flexibility during standard business hours for administrative tasks, research, and strategy development. This is not a passive oversight role—this person will actively audit, coach, and refine both tutoring and counseling delivery to ensure our services consistently meet (and exceed) our premium positioning.
KEY RESPONSIBILITIES
Quality Assurance & Program Governance
- Establish and enforce curricula and session benchmarks across both Counseling and Tutoring to ensure a seamless, "high-narrative" student experience
- Design and lead the QA framework, serving as the final set of eyes on high-stakes student deliverables and the primary escalation point for complex or at-risk client cases
- Regularly audit sessions, student work, and family communications to ensure every touchpoint aligns with our premium brand standards
- Identify service delivery gaps and implement corrective action plans or calibration sessions to ensure consistency across all teams
- Act as a "coach to the coaches," auditing sessions, and providing the rigorous feedback necessary to keep our Lead Counselors and Tutors at the top of their game
- Address underperformance and create pathways to elevate top-tier talent
Strategic Operations & Client Experience
- Monitor client satisfaction and proactively intervene to stabilize outcomes and ensure a high-touch, "white-glove" experience for every family
- Build and manage scalable systems for tracking quality, outcomes, and team performance data
- Analyze cross-departmental trends to advise leadership on the evolution of service offerings, pricing, and delivery models
- Manage a small portfolio of ambitious students, making multi-year commitments to guide them through the entire admissions cycle with a focus on high-impact extracurricular recommendations, narrative building, and essay writing.
- Serve as an escalation point for families and staff, proactively resolving complex issues and assisting with case reassignment when necessary.
QUALIFICATIONS
Education & Experience
- Degree from a Top-50 institution required, advanced degree preferred
- Experience serving in a decision-making capacity on the admissions committee at a selective institution, with a deep understanding of holistic review and selective institutional priorities
- Experience managing teams and navigating high-pressure, high-expectation client environments
- Deep pedagogical knowledge of standardized testing (SAT/ACT) and academic curricula; ability to audit tutoring sessions for instructional efficacy
- Experience managing multi-disciplinary teams in a high-stakes, private educational environment
- Proven success working with a range of student engagement levels, from self-driven over-achievers to those requiring strategic re-engagement and motivational scaffolding
- Familiarity with direct-admit and/or specialized programs at a wide variety of institutions
Skills/Qualities
- Natural ability to connect with others and build trust and rapport quickly with both families and internal staff
- Able to synthesize nuanced information and deliver decisive, confident recommendations
- Genuine passion for helping students achieve their academic and personal potential
- Exceptional organizational mastery and the ability to simultaneously manage multiple complex student lifecycles with precision, particularly in fast-paced environments that require significant emotional intelligence and poise
- Ability to translate complex admissions data and trends into actionable counseling strategies
- Proficiency in using college counseling software, spreadsheets, and data management tools
- Dedicated, quiet workspace with reliable internet access for virtual sessions
COMPENSATION & ADDITIONAL DETAILS
- Salary: This is a full-time, salaried, exempt position with a base of $140,000-160,000 DOE.
- Bonuses: Eligible for incentive and retention bonus plans, as well as a profit-sharing plan.
- Benefits: 401(k) with company match, medical/dental/vision insurance, life insurance, and LTD coverage, technology stipend, paid time off, and more.
We are looking for people who would like to call Great Expectations home for years to come, so if this position piques your interest, please send us a cover letter that demonstrates your creativity, personality, and general writing skills – please be yourself and use this opportunity to show us the real you!
** NOTE: We are extremely dedicated to employee engagement and hiring for the long term. To that end, our recruiting process includes two virtual meetings, an essay editing assignment, a personality assessment, and reference checks. **