System Engineer
Confirmed on the employer's own hiring board on Oct 30, 2026. First seen by Alion on Oct 23, 2026.
We're rebuilding Headway Inc's IT Infrastructure team, and we're looking for a System Engineer to help move it from ad-hoc requests to stable systems and automation. You'll take ownership of key projects in device management, access and software licenses, and see them through from start to finish. This role suits someone who wants real autonomy and visible impact.
About Headway Inc
Headway Inc is a global tech company building products that help people grow. Our apps have reached 170M+ downloads worldwide, and TIME ranked Headway Inc #4 among the World's Top EdTech Companies.
Our achievements start with our people and the values we share. At Headway Inc, we believe in building strong teams around our SELECT values.
Behind every product we ship are around 500 people who need their devices, access and tools to simply work. IT Infrastructure makes that happen: the right setup on day one, no friction in daily work, and offices that keeps running even through blackouts.
What you'll do
Device management: Lead the rollout of device management for our Mac fleet, so every laptop is secure and ready to use from day one.
Software licenses: Build one clear process for all SaaS and AI tools, from requests to renewals and cost control.
Access and collaboration platforms: Administer our core workplace tools and make access to them simple and secure.
Office infrastructure: Keep our office network, servers and backups reliable, including through blackouts.
Employee lifecycle and automation: Make onboarding and offboarding smooth and automate repetitive IT work.
Helpdesk and knowledge: Support colleagues together with the team and turn what you know into documentation everyone can use.
You'll report to Inna Selivon, our Administrative Manager, and work closely with your IT Infra teammates and with teams across the company, from people operations and project management to engineering and security.
What success looks like
Key infrastructure projects, starting with device management, have a clear owner and are brought to completion.
Every Mac is managed and secure, and new laptops are ready to use from the first login.
Software licenses are transparent: every tool has an owner, requests go through one flow, and unused seats are regularly cleaned up.
Access to core apps is centralized and secure, and onboarding and offboarding run smoothly with minimal manual work.
Critical systems are documented, and the team can operate each of them confidently.
The team spends more of its time on projects and automation. Depending on your results and interests, you can grow towards a Senior role or take the lead on technical areas as the team grows.
You'd be a great fit if you
Have experience in system engineering or corporate IT.
Have hands-on experience rolling out an MDM for macOS (ideally Jamf) and setting up SSO and MFA.
Administer Google Workspace and manage software licenses and subscriptions.
Are confident with office networks, VPN, servers, backups and DNS.
Automate routine work with scripts and Jira, and use AI tools every day.
Take ownership of projects and close them end to end: plan the stages, spot risks early and keep stakeholders informed.
Enjoy building processes, treat helpdesk as part of the job, explain technical things simply and document what you know.
Speak English at B2+ level, since you'll work with vendors, documentation and licensing terms.
Align with our team values, SELECT, and put them into practice in the way you work, make decisions and collaborate with others.
It would be a plus if you also have:
Mentoring or informal tech-lead experience.
What we offer
Two week-long paid corporate holidays each year and 20 vacation days.
Medical insurance, full sick leave compensation and access to a corporate doctor.
A personal development plan, professional communities and a knowledge base.
Compensation for English-language learning, external training and courses.
An office with a reliable shelter, generators, satellite internet, and other amenities.
Sports activities, including running, yoga, boxing and more.
Supporting initiatives that help Ukraine. Find out more about our projects here.
We've created a Talent Guide to help you navigate our hiring process with clarity and confidence - and get the most out of each stage. Take a look here.