Director, IT

About Keystone AI:
Keystone AI 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, Keystone AI 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.
Keystone AI is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $55M Series C led by Oak HC/FT https://www.fiercehealthcare.com/health-tech/stepful-banks-55m-scale-ai-powered-infrastructure-tackles-healthcare-staffing-shortage. We were named the #1 EdTech company in the U.S. by TIME for 2025 https://www.stepful.com/post/stepful-named-1-edtech-company-in-us-top-10-globally-times-2025-list.
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:
We're hiring our first Director of IT to build Keystone AI's IT and security function from the ground up. You'll own our path to SOC 2 certification and everything that keeps a fast-growing company running securely — from identity and access management to the laptop that lands on every new hire's desk. This is a hands-on role to start: you'll operate as an individual contributor, set the strategy, and build out a team as the company scales.
This role reports directly to the SVP, Engineering and partners closely with Engineering, Finance, People, and our B2B teams across the organization.
This is a hybrid opportunity based out of our NYC office, requiring three days/week (Tuesday, Wednesday, Thursday) in office.
What you'll do:
– Security & Compliance: Own Keystone AI's security program end to end, leading our SOC 2 effort from readiness assessment through audit and ongoing compliance
– Define and enforce security policies, identity and access management, and least-privilege controls across the organization (SSO, MFA, access reviews)
– Support our B2B healthcare partnerships by owning security questionnaires, vendor assessments, and customer audit requests
– IT Operations: Own the full equipment lifecycle — procurement, MDM deployment, inventory, and seamless onboarding/offboarding for every employee
– Manage our SaaS application stack, including provisioning, access governance, vendor security reviews, and spend optimization
– Build scalable IT support processes and serve as the escalation point for day-to-day IT needs, rolling up your sleeves while the function is small
– Partner with Engineering on incident response, endpoint security, and infrastructure hardening
– Team Building: Define the long-term IT roadmap and build, hire, and lead the team as Keystone AI's needs grow
What you'll bring:
– 8+ years of IT experience, including experience leading IT or security functions at a high-growth startup
– Hands-on experience driving a SOC 2 certification (Type I and II) from readiness through audit
– Deep expertise with the modern IT stack: MDM (e.g., Kandji, Jamf), identity providers (e.g., Okta, Google Workspace), and endpoint security tooling
– Proven ability to operate as a strategic leader and a hands-on individual contributor at the same time
– Strong vendor management skills across hardware, software, and audit partners
– Exceptional communication skills with the ability to make security and compliance accessible to non-technical teams
– A builder's mindset — you're energized by creating processes and systems from scratch, not inheriting them
Bonus points if:
– You have experience with HIPAA or healthcare data compliance
– You've built an IT function from zero at a scaling company
– You've worked in EdTech, healthcare, or another mission-driven industry
Interview Process:
– Introductory call with Talent Acquisition team member
– Interview with Hiring Manager
– Take-Home Assignment and Presentation
– 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
– Open vacation policy, including:

– Guidance of 15 days PTO annually

– Keystone AI 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 $200,000 - $250,000, 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.
Keystone AI 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.