System Engineer

Headway Inc is a global tech company, revolutionizing lifelong learning by creating digital products for over 150 million users worldwide. Our mission is to help people grow. We’re proud to be ranked 4th among the World’s Top EdTech Сompanies by TIME magazine. We believe lifelong learning should be accessible, personalized, and impactful to each individual. That’s how we change the world and why we bring together exceptional minds.
 

The core of our achievements is our team. We believe in people and shared values SELECT. That’s why, together with Oleksandr Kushchynskyi, our Product Manager, we’re looking for a System Engineer to join our team of superstars transforming the EdTech industry.

What team will you be a part of?

Infrastructure Squad ensures smooth operations and scalable growth for the business. The team designs and implements solutions to enhance the daily experience of everyone at Headway Inc.
 

This job is perfect for you if you:

— Want to own and scale corporate IT infrastructure end-to-end, not just “support tickets.”
— Are an A-player who takes initiative, prioritizes well, and thrives in a high-volume, fast-paced environment.
— Enjoy communicating with business stakeholders, translating needs into secure, scalable solutions, and documenting them clearly.
 

What will you do:

— Own and scale on-prem IT infrastructure and network architecture (WiFi, LAN/WAN, VPN, DNS), including backup systems (UPS, hardware backups).
— Administer the corporate SaaS ecosystem end-to-end (Google Workspace, Slack, Notion) and optimize how teams use it.
— Implement and manage security foundations: IAM (Google Workspace, Okta), device management (Jamf), and security policies across all corporate devices.
— Design and build IT process automations to eliminate manual work and improve efficiency.
— Manage IT assets and software licenses lifecycle, maintaining accurate inventory and operational readiness.
— Lead the Jira ITSM environment and maintain a high-standard Internal Knowledge Base.
— Optimize IT operations to a level where they can be smoothly managed by a team (and help shape what that team should look like).
 

What do you need to join us:

— 4+ years of experience in System Administration / IT Operations (or similar roles).
— Strong networking knowledge and hands-on experience managing corporate networks (protocols, VPN, DNS, WiFi).
— Advanced administration of Google Workspace, Slack, and Jira (including ITSM practices).
— Security mindset and experience with MDM (Jamf) and IAM configuration (Google Workspace, Okta).
— Ability to script or use low-code/no-code tools to automate IT workflows and reduce manual operations.
— A strong documentation culture: you enjoy creating clean, structured, and useful docs.
— High ownership, ability to prioritize business needs, and motivation to build/lead a team in the future.
— Alignment with the values of our team (SELECT).
 

What do we offer:

— Work within an ambitious team on a socially impactful education product.
— An office with a reliable shelter, generators, satellite internet, and other amenities.
— Access to our corporate knowledge base and professional communities.
— Personal development plan.
— Compensation for English language learning, external training, and courses.
— Medical insurance and full sick leave compensation.
— Sports activities: running, yoga, boxing, and more.
— Corporate holidays: we go on a week-paid holiday to rest and recharge twice a year. Besides that, we provide 20 paid vacation days per year.
— Supporting initiatives that help Ukraine. Find out more about our projects here.
 

Working schedule:

This is a full-time position. During the 3-month probation period, we ask you to work full-time from our office to get fully onboarded, build strong cross-team collaboration, and dive deep into our IT environment.

After probation, you’ll switch to a hybrid format — you’ll mainly work from the office, with the option to work from home occasionally when needed.
 

Are you interested?
Send your CV!