Lead, Support Operations

About Stepful:

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners—especially those from underserved communities—launch high-demand healthcare careers.

In addition to our direct-to-consumer training, Stepful partners with leading healthcare institutions to build talent pipelines and address the growing shortage of allied health workers. Our graduates, including Medical Assistants, Pharmacy Technicians and more, go on to work at major employers like CVS, NY-Presbyterian, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $31.5M Series B led by Oak HC/FT. Additionally, we were named the #1 EdTech company in the U.S. by TIME for 2025 and to GSV's 150 Most Transformational Growth Companies in Digital Learning.

We’re unlocking the full potential of the global workforce—improving access to quality healthcare for everyone, everywhere.

Our values:

We credit much of our success to our exceptional team. We’re looking for mission-driven individuals who thrive in fast-paced, sometimes ambiguous environments, and embody our four core values:

Care first: We do whatever it takes for our students to succeed.

Learn quickly: We test, learn with data, and iterate.

Build together: We win when we rely on each other.

Own it: We show up, take initiative, and show pride.

The opportunity:

Stepful is seeking a Lead, Support Operations to enhance our operational efficiency as we scale from 25,000 active students to over 100,000 active students. This is a pivotal moment for our organization and an opportunity to be a force-multiplier in streamlining our communications to students across various channels.

The Lead, Support Operations will build systems, identify tooling and leverage AI solutions to standardize how we communicate with students throughout their journey with Stepful: from admissions through to job placement and everywhere in-between.

This is a hybrid role (working three days/week from our office in NYC) reporting into our VP, Operations.

What you’ll do:

• Make Data-Driven Decisions: Create and maintain dashboards and forecasts that inform both resource planning and capacity management

• Frameworks: Build and lead escalation frameworks to address student concerns swiftly and effectively

• Optimization & Standardization: Identify operational gaps and implement solutions to standardize our student communications across various channels and programs

• Enhance Operational Efficiency: Leverage AI-driven solutions to reduce workload on support staff, allowing them to focus on more complex, high-touch tickets

• People Management: Lead a team of support specialists to provide an exceptional student experience

• Customer Advocacy: Act as the voice of the student within Stepful, ensuring their needs are represented and addressed appropriately

• Cross-Functional Collaboration: Work closely with various business partners to improve and optimize the student experience for superior retention, graduation and job placement rates

What you’ll bring:

• At least 8 years of experience in customer support, operations or a similar discipline, preferably within a B2B2C setting

• At least 2 years of people management experience

• Experience managing a complex, multi-faceted customer journey inclusive of various forms of support (i.e., sales support, technical support)

• A proven track record of both optimizing and standardizing support operations through technology and creative solutioning, at scale

• Familiarity with leveraging AI-enabled solutions to automate support

• Experience creating dashboards, tracking metrics and forecasting using tools such as Excel/Google Sheets and/or BI/data visualization tools (Looker, Tableau)

• Empathy for both our support team and our students

• Ability to influence and inspire cross-functional teams

Bonus points if:

• Experience in a high-growth, scaling startup environment

Interview Process:

• Introductory call with Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment

• Virtual Panel

• On-Site Panel Interview

Benefits and Compensation:

• Meaningful Equity Stake

• Subsidized Medical, Dental, and Vision insurance plan options

• 401(k)

• FSA, HSA and commuter benefits

• Open vacation policy, including:

  • Guidance of 15 days PTO annually

  • Stepful closed the last week of December

  • 15 work-from-anywhere days

  • 10 public holidays observed for 2025

The target base salary range for this opportunity is $160,000 - $180,000, and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, internal pay equity and other relevant business considerations.

Stepful is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic.