Director, Enterprise Demand Generation

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 Director of Enterprise Demand Generation you will define and lead Stepful’s B2B marketing strategy, setting the direction for how we scale from product-market fit with our pilot partners to the category-defining talent-pipeline solution for the US healthcare industry.

This role owns our employer-facing positioning, our promotional strategy across content, events, and more, and how we’ll translate our products, services, and insights into demand-generating programs that drive revenue. This is a hands-on, build-phase role for a senior marketer who enjoys setting strategy and is even more excited to execute.

This role reports into our SVP, Growth.

What you’ll do:

Functional Leadership

• Own the B2B marketing strategy, roadmap, and success metrics, with clear alignment to company-level commercial goals

• Make explicit prioritization and tradeoffs across initiatives, audiences, and channels, focusing resources on the highest-impact opportunities

• Act as a senior cross-functional partner to Sales, Product, Learning, Solutions Architecture, and Client Success, leveraging market insights to align stakeholders and priorities.

Positioning, Messaging, & Product Marketing

• Define and own Stepful’s B2B positioning, messaging frameworks, value propositions, and competitive differentiation

• Lead market and competitive research to surface insights that shape positioning, GTM roadmap, and sales enablement

• Develop and maintain core product marketing assets and frameworks (e.g., pitch narrative, ICPs and personas, competitive battlecards, objection handling) that equip sellers to clearly and confidently tell the Stepful story

• Lead launches for new products, programs, and features; own end-to-end rollout including targeting, positioning, and sales collateral in close partnership with Product, Learning, and Solution Architecture teams.

Demand Generation

• Lead B2B demand generation strategy, including account-based marketing, content-driven campaigns across channels, and events

• Position Stepful as a thought leader through compelling content marketing that builds trust in a risk-averse market

What you’ll bring:

• 10+ years of experience in B2B marketing, with a proven track record in product marketing and demand generation, with at least several years experience marketing to large healthcare employers

• Demonstrated delivery against ambitious goals including setting strategy, owning execution it – making decisions and tradeoff

• Excellent storytelling instincts with the ability to craft strong narratives, impactful positioning, and messaging instincts, with the ability to translate these ideas into compelling collateral and equip GTM teams to use them effectively.

• Experience partnering with senior stakeholders across the organization, including Sales, Product, Operations, and executive leadership, proactively collaborating and using insights to drive the business strategy

Bonus points if:

• You have experience marketing workforce or training solutions

Interview Process:

• Introductory call with Talent Acquisition team member

• Interview with Hiring Manager

• Virtual interviews with Sales, Client Success, and other Marketing leadership

• Take-Home Assignment

• Virtual Panel Interview

• On-Site Interview with Founder & SVP, Growth

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 $180,000 - $210,000, and is part of a competitive total rewards package including 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.