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Head of Operations

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: Vintti
Full Time position
Listed on 2026-10-30
Job specializations:
  • Education / Teaching
    Tutoring
Salary/Wage Range or Industry Benchmark: 95000 - 130000 USD Yearly USD 95000.00 130000.00 YEAR
Job Description & How to Apply Below

We are looking for an Operations & Tutor Success Lead to drive the end-to-end supply chain, scheduling logistics, capacity planning, and overall performance of our tutor network across Latin America. This is an operations-first role designed for a "mini-founder" who thrives in high-complexity environments: someone who can optimize supply and demand, streamline scheduling workflows, manage unit economics, and build scalable operational playbooks.

Think of this person as our "Head of Fleet Operations" (Uber / Rappi marketplace style) for tutors: a supply chain and operations operator who masters capacity planning to protect gross margins, eliminates operational friction, and keeps our tutor community highly engaged, active, and performing. A tutor's operational efficiency directly impacts session quality, overall retention, and unit profitability.

Today, this is a hands-on, individual-contributor role owning supply operations, capacity logistics, and tutor engagement. As volume grows, this role will scale into leading the broader Tutor Operations and Supply division.

Responsibilities
Tutor Experience, Retention & Community (Uber-Style Driver Success)
  • Own the Day-to-Day Tutor Journey: Keep tutors motivated, supported, and engaged. Act as the primary point of contact for tutor concerns, payment questions, and scheduling issues.
  • Gamification &

    Incentives:

    Design and implement tutor incentive schemes (completion bonuses, performance perks, gamification) to boost punctuality, session quality, and retention.
  • Referral & Community Building: Launch tutor referral programs and build a strong tutor community to create an ongoing pipeline of top talent.
Supply Operations, Logistics & Capacity Planning
  • Capacity & Demand Planning: Work closely with operations to build long-range capacity plans, ensuring we have the exact bench of bilingual tutors needed for upcoming student "waves."
  • Logistics & Scheduling Optimization: Optimize tutor shift allocation (back-to-back scheduling) to maximize tutor utilization while avoiding no-shows or late arrivals.
  • Unit Economics & Margin Target: Monitor supply costs and operational efficiencies to help safeguard our target Gross Profit Margin / COGS (maintaining a 70%+ margin).
Recruiting & University Partnerships
  • Targeted Recruiting: Lead tutor acquisition across Lat Am, prioritizing high-quality bilingual talent (specifically strong in Math/Algebra and History).
  • University Partnerships: Build relationships with universities across Lat Am to establish a reliable pipeline of student tutors.
  • Career Path Model: Position tutoring as a career on-ramp, connecting top-performing tutors to future career growth opportunities within the company.
Requirements
Must-Haves:
  • Experience: 4+ years of combined experience in Recruiting, HR, Talent Acquisition, Operations, or Client Success
    .
  • Soft Skills & Relationship Management: Strong empathy, interpersonal skills, and ability to build trust and high engagement within the tutor community.
  • Numerical & Business Acumen: Comfort working with operational metrics, unit economics, and margin tracking (understanding EBITDA, Gross Margin, and capacity utilization).
  • Technical Toolkit:

    Google Sheets / Excel (Advanced):
    Ability to build and maintain custom operational sheets, schedules, and capacity projections.
  • Vibe Coding / AI Prompting: Proficiency or strong familiarity using AI tools (ChatGPT, Claude, prompting) to quickly automate workflows, scripts, or operational tasks.
  • Languages: Fluent/Professional English and Spanish (written and verbal).
  • Ownership Mindset: Entrepreneurial spirit, proactive attitude, and ability to thrive in a fast-paced environment.
Nice-to-Haves:
  • Marketplace / Logistics Background: Previous experience at high-growth marketplaces or mobility platforms (
    Uber, Rappi, Pedidos Ya
    , etc.) managing driver/rider supply or operations.
  • Internal HR: Willingness to support basic internal HR/people tasks as the team scales (
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