Support Agent (AI & Automation)

Headway Inc; United States; Hybrid; USD 42,000 - 65,000; Full time

Benefits offered by this job

Medical insurance

Sick leave compensation

Hybrid work option

Corporate holidays

Job summary

Headway Inc is a global tech company focused on lifelong learning, serving 170 million users. We’re building an AI-powered support framework and are looking for a Support Agent to help customers, investigate complex tickets, and contribute to product decisions.

In this full-time, hybrid role, you’ll collaborate with Product, Engineering, and Payments to deliver thoughtful help. You’ll grow into automation, analytics, and a knowledge base while maintaining a strong focus on outcomes and user

Qualifications

• Experience in customer support or a user-facing role.
• Excellent written and spoken English communication.
• Ability to work with AI-powered tools and adapt to evolving processes.

Responsibilities

• Handle complex user cases requiring empathy and product understanding.
• Work with AI tools to monitor quality and improve automation.
• Audit and improve support processes for scalability.
• Act as a bridge between users and product team to surface insights.
• Proactively detect anomalies or spikes in user requests.

Skills

Customer support

English proficiency

Analytical thinking

Collaboration

Job description

Headway Inc is a global tech company, revolutionizing lifelong learning by creating digital products for over 170 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.

We believe in people and shared values SELECT. That’s why, together with Alona Sharai, Head of Support at Headway Inc, we’re looking for a Support Agent to help build scalable AI-powered support while influencing product decisions.

The team you'll be working with

Support works with almost every product at Headway Inc, in close contact with Product, Engineering, and Payments. Automation handles the routine. What reaches you is what it couldn't: tickets where the right call isn't obvious, users who've already had an answer and still don't have a solution.

How you grow here

Once your work on tickets is stable, you start taking on more alongside it – automations, analytics, knowledge base, the hardest cases – and eventually go deep in whichever direction fits you. The opportunities are there. Which ones you take, and when, is your call.

Why this is exciting

• Support here is being rebuilt, not maintained. Automation is already in production and carrying live volume. You'll be working with that system, and on it, as the agent role keeps shifting toward quality and analysis.

• Room to build instead of repeat. When volume allows, that time goes to learning and projects.

• A team that values proactivity, systemic thinking, and openness to feedback.

This role is your calling if you

• Take a problem to the end instead of handing it over, even when the end is three teams away.

• Ask why a flow exists, and notice when the answer doesn't hold up.

• Talk in outcomes: what you changed, why it mattered, how you know it worked.

• Pick up new tools fast and are comfortable around technology, AI included.

• Keep working well when priorities and processes move under you.

• Want feedback and aren't afraid to challenge the status quo.

• See support as a business function.

• Have some experience in support or another user-facing role. Mindset counts more than years.

• Communicate confidently in English (Upper-Intermediate and higher).

What you'll do

• Handle complex user cases that require empathy and deep product understanding rather than templated responses.

• Work in synergy with AI tools: monitor response quality and continuously improve automation.

• Audit and improve support processes: identify inefficiencies and initiate scalable solutions.

• Act as a bridge between users and the product team by surfacing insights and recurring issues.

• Proactively detect anomalies or spikes in user requests and help mitigate risks early.

• Grow into the work behind the tickets – automations, analytics, and the knowledge base other agents rely on

What to know going in

• Day-to-day, this is agent work. User requests are the core of the job, and the automation and process side grows out of that rather than replacing it.

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.

• Supporting initiatives that help Ukraine. Find out more about our projects here.

Working schedule

This is a full-time position with a hybrid remote option. It means that you can decide for yourself: whether you want to work from the office, remotely, or combine these options.

Support works in shifts: 8 hours a day, either Sunday to Thursday or Tuesday to Saturday.