Stepful
What It's Like to Work at Stepful
Frequently Asked Questions
Stepful supports employee job satisfaction through a combination of comprehensive benefits and a mission-driven culture.
Our benefits include (but are not limited to):
- Hybrid work model: most FTEs work out of our open concept NYC office on Tuesdays, Wednesdays and Thursdays. We believe that in-person collaboration fosters innovation, strengthens culture, and accelerates decision-making.
- Uncapped PTO policy: allows employees the flexibility to take time off as needed while ensuring business continuity.
- To maintain a healthy balance, employees are encouraged to take 15 days of PTO annually.
- 15 Work From Anywhere (WFA) days annually: to provide employees with additional flexibility while maintaining business continuity
- Subsidized Medical, Dental, and Vision insurance plan options
- FSA, HSA and commuter benefits
- The option to participate in a 401(k) plan
- Annual Learning & Development Stipend: providing financial support for employees to pursue professional learning opportunities that enhance skills and knowledge relevant to their role or career path at Stepful
- Social connection:
- Quarterly team-building activities to foster collaboration and engagement amongst our team
- Monthly happy hours
- Biweekly company-wide all-hands meetings
Additionally, we place a heavy emphasis on our mission: to help underserved individuals launch healthcare careers. This is emphasized through our four core values: ‘care first,’ ‘learn quickly,’ ‘build together’ and ‘own it.’
Given Stepful is a Series B startup, there is a level of fluidity inherent in most positions at the company. Roles are not always highly structured and, as a result of changing business needs, there is an expectation that employees will occasionally find themselves navigating ambiguous situations without a defined playbook.
That being said, in 2025 Stepful launched a formal career and leveling framework in concert with twice-annual performance reviews to address concerns about career progression.
Stepful Employee Perspectives
What is your role, and what attracted you to Stepful? Describe the moment when you knew you’d found the right fit.
I originally joined Stepful as the first engineer. Back then, Our Chief Product Officer Tressia, our Chief Technology Officer Edo and I were a three-person product team building the first version of our online school. I was hooked almost immediately on our sole focus: building a rebellious online learning experience for adults entering the healthcare field. Traditional online learning often involves lengthy videos and passive content, but we deliberately broke away from this by building our own learning management system, emphasizing bite-sized, interactive lessons and personalized coaching.
We’ve since scaled to having tens of thousands of monthly active students on our platform and built out our engineering team to over a dozen incredibly talented engineers. I’ve been able to continue to embrace the spirit of continuous growth and have taken on an engineering manager role on our “learning experience” team.
What’s your favorite part about working at Stepful?
The one thing that continues to impress me is the caliber of each person here. We all come from wildly different backgrounds, yet you can trust anyone at the office to take a task and own it from start to finish. Working at a startup means we have to break our assumptions often and learn new skills, and it’s great to be able to trust anyone with discovering what it will take to make something happen.
I saw this scrappiness in action during our latest companywide hackathon. Several new employees, only two weeks into their roles, created end-to-end solutions addressing key pain points for students and staff. For instance, Uttara, our new operations manager, quickly identified that manually personalizing outreach messages was slowing us down. Within a few hours, she had built a functional Chrome extension using large language models, significantly increasing the tone and consistency of our outreach.
What advice would you give to job seekers looking to join your growing team?
Two core values we deeply care about at Stepful are “Care first” and “Own it.” Every day, our goal is ensuring our students not only pass their certification exams but also successfully land jobs. When hiring, I look for people who’ve built user-centric products or experiences. Demonstrating side projects, previous edtech experience or even just a clear passion for outcomes-driven environments goes a long way.
