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.

Backround

As Stepful has grown, student communications have expanded across multiple Product squads and Operations teams. This has enabled teams to move quickly and support students at many points in their journey, but it has also created an opportunity to bring greater consistency, visibility, and shared standards to how we communicate.

Today, student-facing messaging is shared across many teams: Growth, Student Experience, Careers, Partner Experience, and Operations. We want to establish a clearer end-to-end view of what students receive between enrollment and graduation, understand which communications are most effective, and create a sustainable operating model for how teams build and manage student outreach going forward.

The Role

We are looking for a contract Student Engagement Manager to help bring greater structure and consistency to Stepful’s student communications: what we send, when we send it, how it reads, and how multiple teams contribute to the experience.

This is a hands-on role. You will work directly in Customer.io to audit and improve existing campaigns and workflows, partner with Product and Operations to map the current student journey, and create clear processes and standards that teams can continue using after the engagement ends.

We are intentionally scoping this as a 1099 contract role (remote - NYC) because the immediate opportunity is well defined: establish the foundation, simplify the existing communication ecosystem, and leave behind systems and standards that the broader team can maintain.

Scope of Work

1. Map the student communications journey

Timing: Weeks 1–4

• Create an end-to-end view of student communications from enrollment through graduation.

• Document messages by channel, trigger, timing, and owner.

• Identify areas of overlap, gaps, or opportunities to improve clarity and effectiveness.

• Develop a prioritized list of communications opportunities tied to student retention, engagement, and graduation.

2. Optimize and organize Customer.io

Timing: Weeks 3–8

• Audit active campaigns, segments, triggers, and templates.

• Retire outdated or duplicative workflows where appropriate.

• Establish clear naming, tagging, and organizational conventions.

• Document active workflows and ownership so teams can navigate and maintain the platform confidently.

3. Build a multi-squad communications operating model

Timing: Weeks 6–10

• Create a lightweight process for proposing, reviewing, launching, and retiring student communications.

• Establish intake, QA, and review standards.

• Create shared visibility into upcoming sends and potential communication conflicts.

• Define practical ownership and decision-making guidelines across teams.

4. Establish communications strategy and style guidelines

Timing: Weeks 8–12

• Document voice and tone principles for student communications.

• Define recommended structures and standards for email and SMS.

• Establish guidance for channel selection, including when to use email, SMS, or in-product messaging.

• Create guidelines that Product Managers and operators can apply independently.

Out of Scope

• Owning Stepful’s broader student engagement strategy or Product roadmap.

• Acquisition and top-of-funnel marketing communications.

• B2B or partner-facing communications.

• People management or squad leadership.

• Building new product surfaces that require engineering work.

If the engagement identifies product or engineering opportunities, those will be documented and handed off to the appropriate squad.

What Success Looks Like

At the end of the engagement:

• Stepful has a single, up-to-date view of the student communications journey, with clear ownership across touchpoints.

• Customer.io is organized, documented, and easier for teams to navigate and maintain.

• Product and Operations teams have a clear process for proposing, reviewing, launching, and retiring communications.

• Shared voice, structure, and channel standards are documented and reflected in student messaging.

• The team has a prioritized, evidence-informed set of opportunities to improve student retention, engagement, and graduation through communications.

Engagement Details

• Shape: Approximately 3-month contract engagement, with a midpoint check-in to assess progress and future needs.

• Commitment: Approximately 20–30 hours per week.

• Reports to: Director of Product.

• Day-to-day partnership: Student Experience Product team.

• Key collaborators: Product Managers, Operations, Design, and Data.

• Potential future opportunity: Based on business needs and the outcomes of the engagement, Stepful may evaluate whether student engagement warrants a permanent owner.

Who Fits

We are looking for a lifecycle, CRM, or student/customer engagement professional who has personally improved and organized an existing marketing automation environment.

Strong candidates will bring:

• Hands-on experience with Customer.io, Braze, Iterable, or a similar lifecycle automation platform.

• Experience auditing, reorganizing, and improving existing campaigns, workflows, segments, and triggers.

• Experience with lifecycle communications tied to retention, engagement, completion, or similar outcomes— especially for products with long usage periods, where retention is key.

• Strong writing judgment and the ability to create voice and messaging standards that others can follow.

• Comfort introducing structure and shared processes across cross-functional teams without formal authority.

• The ability to operate independently, make practical decisions, and leave behind documentation and systems that others can maintain.

Experience in education, healthcare training, subscription, community, or another business with a complex user journey is a plus.

The hourly rate range for this opportunity is $60.00/hour - $90.00/hour. 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.