The Head of Operations will serve as the operational and business leader across all Collegiate Storytellers entities and ventures, reporting to and partnering closely with the Founder. The Founder retains ownership of methodology, client relationships, content, and creative direction. The Head of Operations’ mandate is to build the infrastructure, team, revenue engine, and brand visibility that allows the Founder’s work to reach more families, more markets, and more stages—without diluting quality.

This is a ground-floor leadership opportunity in a company with strong client demand, a differentiated methodology, and significant room to scale.

To be considered, please submit your resume and a brief note (no more than one page) explaining why this role interests you and what experience you'd bring to a founder-led business. Send to info@collegiatestorytellers.com.

Core Responsibilities

Business Operations & Infrastructure

Oversee the day-to-day operations across Collegiate Storytellers and The Essay Academy, including workflow systems, scheduling, CRM, and client onboarding processes. Establish and refine operational procedures that support a high-touch, relationship-driven consulting model. Manage vendor relationships, technology platforms, and administrative functions.

Financial Management

Own the P&L. Develop and manage annual budgets, pricing strategy, and revenue forecasts. Track key business metrics—client acquisition cost, retention, revenue per client, capacity utilization—and report to the Founder regularly. Identify opportunities to improve margins without compromising the client experience.

Team Building & Management

Hire, manage, and develop staff across operations, client support, and editorial functions. Serve as the direct manager for operational and support team members. Build a team culture aligned with the firm’s values of intellectual rigor, honesty, and personalized attention.

Freelance Advisor Network

Source, recruit, and onboard freelance advisors who meet the firm’s quality and methodology standards. All advisor hires are subject to Founder approval. Manage freelance advisor contracts, compensation, workflow, and quality oversight. Build training and onboarding systems that allow advisors to deliver the Collegiate Storytellers methodology consistently.

Business Development & Growth

Develop and execute marketing and lead-generation strategies across digital, referral, partnership, and community channels. Represent the company in business contexts—networking, partnerships, local and industry events. Identify and evaluate potential new lines of business or service extensions, presenting opportunities to the Founder for strategic alignment review before execution.

Founder Brand & Thought Leadership

Manage the logistics and business development pipeline for the Founder’s speaking engagements, including booking, contracts, fees, and travel coordination. Oversee the business side of book development—agent and publisher outreach, proposal coordination, and timeline management (not the writing itself). Build and manage the infrastructure for a storytelling methodology product, whether that takes the form of a certification program, workshop series, digital course, or licensing model for other IECs. Identify and pursue strategic partnerships that elevate the Founder’s visibility as a thought leader in the admissions space.

Brand & Marketing Oversight

Oversee the execution of marketing initiatives, ensuring consistency with the firm’s voice and positioning. The Founder sets the voice; the Head of Operations ensures it is amplified. Manage the company’s digital presence, including website, social media strategy, and any paid marketing efforts.

What This Role Is Not

This person does not develop admissions strategy, write or edit essays, advise families on school selection, or make methodology decisions. The Founder is the firm’s intellectual and strategic authority. The Head of Operations’ job is to make the Founder’s work reachable by more families, delivered more smoothly, and supported by a team and infrastructure worthy of the product.

Requirements

• Experience running operations at a small to mid-size professional services, education, or consulting firm
• Proven P&L ownership (managed revenue, expenses, and margin directly)
• Experience building and managing small teams (3 to 15 people)
• Marketing and business development experience in relationship-driven or local markets
• Comfort working in a founder-led company where creative and strategic authority stays with the Founder
• Strong written and verbal communication skills

Preferred but not required

• Familiarity with the college admissions landscape
• Experience managing freelance or contract workers
• Experience supporting a founder's brand expansion (speaking, publishing, partnerships)