About Stepful

Stepful is a workforce platform redefining how America's largest health systems build, train, and retain their talent. Since our founding in 2021, Stepful’s trained over 32,000 practice-ready healthcare workers.

Layering onto our successful direct-to-consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare career ladders for those who need them most.

Our students form the talent pipelines for major employers such as NY-Presbyterian, Mt. Sinai, HCA, Providence, CVS, and Walgreens. We have partnerships with half of the top 10 health systems in the US and are in process with many more.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $55M Series C led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.

Our Values

We credit much of our success to our exceptional team. We’re looking for mission-driven builders who thrive in fast-paced, 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.

About The Role

You will own the end-to-end student engagement surface as a product. Students stall in predictable places (e.g. between signup and enrollment, before their first class, when momentum dips mid-program). Right now, the comms that should catch them are scattered across teams and tools, with overlap in some places and gaps in others. Your job is to turn that into one coherent engagement engine: a system that understands where a student is, decides the right next action, and runs it reliably without someone manually pushing every step.

You'll do this hands-on, building directly in tools like Customer.io rather than handing specs to someone else. But the tools are the implementation detail. What we actually need is someone who owns the outcome—students moving forward with clarity and confidence—and has the judgment to design the logic, the measurement, and the guardrails behind it.

This is a builder-and-owner role with real decision authority over the student comms stack. It reports into Product. If you want a mature lifecycle function with established playbooks, this isn't it. If you want to build that function, it's yours.

What You'll Own

The end-to-end student comms surface. Every touchpoint from course enrollment through payment, onboarding, pre-class readiness, activation, and success milestones; owned as one coherent system rather than a set of disconnected sends.
The decisioning logic behind next-best-action. The triggers, segmentation, branching, routing, and escalation that decide what happens for a given student based on their behavior and context, including when to send, when to route a question, and when to hand off to a human.
The measurement system. How we know engagement is working: the metrics, experiments, holdouts, and goals that prove a flow moves students forward, and the discipline to kill what doesn't.
The guardrails. The standards that keep automated and AI-assisted communication clear, supportive, and human. Scaled comms feel like a great admissions advisor or coach, not a chatbot.

What Success Looks Like

In your first 90 days, you might:

Map the existing student lifecycle end-to-end and untangle where comms currently overlap, conflict, or leave gaps. You turn the current fragmented picture into a single source of truth.
Cut the redundant and competing sends that create noise across the student journey, and establish a clear logic for what fires when.
Ship one measurably better flow. For example, a redesigned activation or pre-class readiness sequence with a real success metric and a holdout to prove the lift.

Over time, you'll move Stepful from fragmented, team-by-team outreach to a coordinated engagement engine that scales with the business and helps every student take the next step with clarity and confidence.

You may be a fit if

You've built a lifecycle, growth, or engagement system that ran at scale without you manually operating every step and you can point to the outcome it drove, not just the workflows you shipped.
You're energized by replacing manual processes with systems, and you build directly in automation, CRM, or workflow tools rather than only writing briefs.
You can reason through a full workflow end-to-end: what triggers it, what context it needs, what logic powers it, what channel it uses, when it escalates, and how success is measured.
You understand student (or user) motivation well enough to design communication that helps people act without feeling robotic, spammy, or confusing and you care about owning the outcome, not just the build.
You're practical and curious about AI as a way to improve workflow design, routing, personalization, QA, and scale (not just to generate content).

Helpful background (not required): hands-on experience with a lifecycle/automation platform (Customer.io, Braze, Iterable, HubSpot, Klaviyo, or similar); AI agent or support-automation tools (e.g., Decagon); SQL, APIs, webhooks, or low-code tools (Retool, Zapier, Make, n8n); and a complex-user-journey domain like edtech, healthcare, marketplace, or consumer subscription.

This role is probably not for you if

You prefer managing campaign calendars over building systems.
Your experience is primarily top-of-funnel, brand, content, or creative marketing with limited automation or workflow-building.
You prefer writing strategy or briefs but don't want to build directly in tools.
You need a mature lifecycle function and fully defined processes already in place.
You're excited by AI mainly for content generation, rather than for solving practical workflow problems.
You're a pure technical builder who doesn't want to own messaging quality, student experience, or business outcomes.

Benefits And Compensation

Base compensation range: $111,000 - $160,000

Meaningful Equity Stake
Subsidized Medical, Dental, and Vision insurance plan options
401(k)
FSA, HSA and commuter benefits
Learning stipend
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 2026

Interview Process

Step 1: Intro Call with a Talent Acquisition Partner (30 mins)

Step 2: Interview with the Hiring Manager (45 mins)

Step 3: Case Study (45 mins)

Step 4: Onsite interview at Stepful HQ in SoHo, NYC (2 hours)

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.

Compensation Range: $110K - $160K

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