SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Salary: USD 111,000 - 160,000 / annual
Stepful is a workforce platform training healthcare workers for America's largest health systems. Since 2021, Stepful has trained over 32,000 practice-ready healthcare workers and partners with half of the top 10 US health systems. The company is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $55M Series C led by Oak HC/FT, and was named the #1 EdTech company in the U.S. by TIME for 2025.
You will own the end-to-end student engagement surface as a product. Students stall in predictable places—between signup and enrollment, before their first class, when momentum dips mid-program. Currently, the communications 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 manual intervention.
You'll work hands-on, building directly in tools like Customer.io rather than handing specs to someone else. The tools are the implementation detail; what's needed is someone who owns the outcome—students moving forward with clarity and confidence—and has the judgment to design the logic, measurement, and guardrails behind it. This is a builder-and-owner role with real decision authority over the student comms stack, reporting into Product.
You will 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 disconnected sends. You'll design 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. You'll build the measurement system: metrics, experiments, holdouts, and goals that prove a flow moves students forward, and the discipline to kill what doesn't. You'll establish guardrails that keep automated and AI-assisted communication clear, supportive, and human—scaled comms should feel like a great admissions advisor or coach, not a chatbot.
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'll cut redundant and competing sends that create noise, establish clear logic for what fires when, and ship one measurably better flow—for example, a redesigned activation or pre-class readiness sequence with a real success metric and holdout to prove 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.
REQUIREMENTS:
- At least 5+ years of experience building lifecycle, growth, or engagement systems that ran at scale without manual operation, with demonstrated outcomes (not just workflows shipped)
- Energized by replacing manual processes with systems; build directly in automation, CRM, or workflow tools rather than only writing briefs
- Ability to reason through full workflow end-to-end: triggers, context, logic, channel, escalation, and success measurement
- Understanding of student/user motivation to design communication that helps people act without feeling robotic, spammy, or confusing; ownership of outcomes, not just the build
- Practical and curious about AI as a way to improve workflow design, routing, personalization, QA, and scale (not just content generation)
Helpful background (not required): hands-on experience with lifecycle/automation platforms (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); experience in complex-user-journey domains like edtech, healthcare, marketplace, or consumer subscription.
