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.
The opportunity:
We're hiring a Revenue Operations Analyst, with a keen eye towards leveraging AI, to manage and improve the blossoming data infrastructure and reporting systems that power Stepful's B2B commercial growth.
This is a high-impact role for someone who is passionate and knowledgeable about AI, analytically rigorous, scrappy, and excited to build something from the ground up. You'll report to the Director of Revenue Operations and work closely with our commercial and finance teams.
This hybrid role is based out of our lower Manhattan office (in-office T/W/Th).
What you'll do:
AI-focus
Build and deploy automated workflows across Claude, HubSpot, Slack, and our GTM stack to eliminate manual handoffs and reduce AE, CSM, and SA administrative burden
Identify high-friction processes across the pipeline and replace them with scalable automation (e.g., lead routing, renewal triggers, health score alerts, onboarding sequences)
Experiment with and build within AI tools (Clay, ChatGPT, Claude, etc.) to enrich data, generate insights, and accelerate commercial team workflows
CRM & Data Infrastructure
Leveraging AI, serve as a key admin and steward of HubSpot, ensuring data quality, pipeline hygiene, and process adherence across commercial teams
Design and maintain scalable CRM workflows, properties, and stages that reflect how the business operates
Identify and resolve data gaps or inconsistencies before they impact reporting or forecasting through building AI-automated data quality checks and enrichment workflows so inconsistencies are caught before humans notice them
Own our GTM tech stack evaluation and integration (e.g., you decide what connects, how, and why)
Process & GTM Support
Partner with Sales, Client Success (CS), and Solution Architecture (SA) to document, optimize, and operationalize GTM processes from lead routing and handoff to renewal and expansion motions
Support territory planning, account segmentation, and capacity modeling as we scale the commercial team
Identify friction points in the pipeline funnel and propose data-backed solutions to remove them
Be a go-to analytical resource for Sales, CS, SA, and leadership
Reporting & Analytics
Leveraging AI, build and maintain dashboards and reports tracking pipeline health, bookings and revenue attainment, sales velocity, client health, and client retention across our B2B business
Develop and manage cohort analyses, forecasting models, and ad hoc analyses that help leadership make fast, informed decisions and support routine board and All Hands meetings
Own our core commercial metrics (bookings, bookings retention, time-to-close, activation rates, client health scores) and ensure consistent definitions and usage across teams
Partner with Finance on bookings and revenue reporting
What you'll bring:
2–4 years of experience in Revenue Operations, Sales Operations, Business Operations, or a related analytical role
Strong proficiency in Excel and/or Google Sheets, including pivot tables, XLOOKUP, SUMIFS, AVERAGEIFS, and array formulas
Hands-on experience with HubSpot (or a comparable CRM) with a strong grasp of pipeline management and data hygiene
Experience building dashboards and reports—whether in a BI tool (Looker, Tableau, etc.) or directly in HubSpot
Analytically rigorous and detail-oriented: you catch data inconsistencies before others do and you care about getting the numbers right
Proven experience using AI to improve the commercial teams’ efficiency via data and reporting analysis and building automation & workflows
Strong communicator who can translate complex analyses into clear narratives for non-technical stakeholders
Comfortable operating in ambiguity and excited to build processes where none exist yet
Mission-driven and energized by the idea of bringing data clarity to a team doing meaningful work
Required Technical Skills
Workflow automation: We care just as much about what you've automated as what you've manually built. If you've replaced a spreadsheet with a workflow, tell us about it!
Excel/Sheets Skills:
Build and manipulate pivot tables and charts
Use XLOOKUP, VLOOKUP, SUMIF, COUNTIF, AVERAGEIFS, and nested IF formulas
Write array formulas including BYROW, LAMBDA, FILTER, and UNIQUE
Apply conditional formatting and data validation
Bonus: INDEX + MATCH, query functions, and Google Apps Script or Excel macros
Bonus points if:
You have EdTech and/or healthcare experience
You've worked in a B2B2C setting
You have experience with Gong, HubSpot, or other GTM tooling
Interview Process
Introductory call with Talent Acquisition team member
Interview with Hiring Manager
Take-Home Assignment
Virtual Panel Interview
On-Site Panel Interview
Benefits & 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 $100,000 - $120,000, 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.
Please note we do not have a bonus structure at this time so all cash compensation will come in the form of base salary. The total compensation package will also include our benefits package and an equity (ISOs) package.
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.