Senior Operations Manager, Career Coaching

Stepful Inc.

Job Overview

Location

New York City

Job Type

Full-time

Full Job Description

📋 Description

• Own the end-to-end career coaching and externship experience for direct-to-consumer (D2C) students at Stepful, scaling operations from 30,000 to 100,000+ active monthly students.
• Lead a growing team of coach managers and frontline career coaches, developing their skills, setting performance standards, and fostering a culture of accountability and excellence.
• Design and implement scalable operating infrastructure using AI tools like Claude to automate workflows, create playbooks, and build quality frameworks that enable high-quality placement outcomes without proportional headcount growth.
• Drive key placement metrics including placement rates, time-to-placement, employer satisfaction, and student career outcomes, identifying gaps and building data-driven action plans to close them.
• Experiment with new approaches to career coaching, externship matching, and employer engagement, using data to evaluate effectiveness and rapidly iterate on successful models.
• Collaborate cross-functionally with Product, Learning, and Engineering teams to translate coaching team insights into product improvements that enhance student career success.
• Build systems and processes that support consistent, high-quality outcomes as the organization scales rapidly in a fast-paced, ambiguous environment.
• Focus on leveraging technology and automation to increase efficiency and reduce operational friction while maintaining student-centered care and outcomes.
• Monitor and optimize the student journey from enrollment through job placement, ensuring alignment with employer needs and industry demands in allied healthcare.
• Act as a strategic partner to the Group Operations Manager, contributing to broader operational strategy and organizational growth initiatives.
• Maintain a deep commitment to Stepful’s core values: Care first, Learn quickly, Build together, and Own it, ensuring all operations prioritize student success and equity.
• Identify and implement best practices in workforce development and career coaching that can be replicated across growing student populations and new program verticals.
• Ensure coaching operations align with partnerships with major healthcare employers such as CVS, NY-Presbyterian, HCA, Providence, and Walgreens.
• Balance long-term strategic planning with hands-on execution, rolling up sleeves to solve urgent operational challenges while building sustainable systems for the future.
• Use data to inform decision-making, track progress against KPIs, and communicate results to leadership and cross-functional stakeholders.
• Foster a coaching culture that emphasizes continuous learning, feedback, and improvement across all levels of the career coaching team.

🎯 Requirements

• 3+ years of operations or consulting experience
• 2+ years in a D2C startup environment
• Experience managing managers, not just individual contributors
• Strong analytical skills and a track record of using data to improve outcomes at scale
• Ability to hold strategy and execution at the same time — you can set the direction and roll up your sleeves
• Comfort operating in a high-growth, fast-changing environment

🏖️ Benefits

• Opportunity to work at a #1 U.S. EdTech company named by TIME for 2025
• Backed by Y Combinator, Reach Capital, AlleyCorp, and Oak HC/FT with $55M Series C funding
• Mission-driven work improving access to healthcare careers for underserved populations
• Collaborative, fast-paced environment focused on innovation and impact

Skills & Technologies

Senior

Onsite

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Stepful Inc.

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About Stepful Inc.

Stepful offers online training programs that prepare people for entry-level healthcare jobs such as medical assistant, phlebotomy technician, and EKG technician in as little as four months. The company partners with healthcare employers to align curriculum with workforce needs and provides job placement support, including resume coaching and interview preparation. Students learn through live virtual classes, hands-on simulations, and clinical externships arranged in their local markets, aiming to increase diversity and upward mobility in the allied health sector.

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