About Stepful:

Stepful is reimagining allied healthcare training by offering affordable, online, instructor-led, and AI-supported programs that help learners—regardless of background or circumstance—launch high-demand healthcare careers.

In addition to our direct-to-consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. Our graduates, including Medical Assistants, Pharmacy Technicians, Nurses, and more, form the talent pipelines at major employers like CVS, NY-Presbyterian, HCA, Providence, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $31.5M Series B led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.

We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare careers for those who need them most

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.

The opportunity:

As a Senior Engagement Manager on Stepful’s Workforce Solutions team, you’ll be at the forefront of helping healthcare employers tackle one of their most pressing challenges: building the workforce of the future. You’ll work directly with leaders at major health systems to design and configure Stepful programs—tailoring them to each partner’s needs while ensuring solutions are practical, scalable, and set up for measurable success.

This is a strategic, cross-functional role. You’ll partner with Sales to shape deal strategy, collaborate with Learning, Operations, and Client Success to de-risk delivery, and act as a thought partner to clients—sharing best practices from across the industry. Beyond individual deals, you’ll help shape Stepful’s go-to-market motion and strengthen our position as a trusted partner to healthcare employers nationwide.

What you’ll do:

In this role, you can expect to:

• Lead program design conversations during the sales process, facilitating client discovery to uncover client goals, operational realities, and implementation risks

• Drive alignment with employer partners to configure Stepful programs to fit client needs

• Lead internal cross-functional alignment, surfacing program design and delivery considerations and driving alignment across internal teams are ready for launch

• Accelerate deal cycles by clarifying dependencies and enabling decision-making for clients and internal stakeholders

• Join and lead early and critical client meetings to present solution options, share best practices, and position Stepful as a thought partner

• Serve as the implementation lead, ensuring the solution for each client is set for launch and understood by post-sales teams

• Act as a subject matter expert on Stepful’s programs, delivery models, and workforce development trends

What you’ll bring:

• You have experience managing senior client relationships at large, complex organizations—building trust, navigating difficult conversations, and influencing decisions

• You have very strong project management skills, able to drive complex, multi-stakeholder program design and implementation planning

• You bring commercial acumen – a knack for understanding opportunities to better serve a client, and the ability to influence toward deepening a partnership

• You love operating both at both the “big picture” and “detailed” altitudes – you can think strategically, and execute to bring that vision to life

• You excel at influencing without direct authority, structuring and facilitating effective conversations that surface issues and generate actions on decisions from cross-functional owners

• You are data- and outcomes-driven, using metrics to refine solutions and ensure success

• You thrive in fast-paced, evolving environments and are excited to help build processes for scale

Bonus points if:

• Experience in solution consulting, management consulting, or a B2B go-to-market role (sales, client success, partnerships)

• Background in education, healthcare, workforce development, or tech-enabled services

• Excitement to build a new function—codifying playbooks, tools, and best practices for scale

Interview Process:

• Introductory call with Talent Acquisition team member

• Interview with Hiring Manager

• Take-Home Assignment

• Virtual Panel Interview

• 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

• 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

The target base salary range for this opportunity is $145,000 - $165,000, and is part of a competitive total rewards package including a performance-based cash bonus, 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.

Compensation Range: $145K - $165K