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Executive Technical Support Engineer Jobs in Chicago, IL

Flywire

Technical Support Engineer II

Chicago, IL · On-site

The Opportunity We are seeking a highly motivated and talented Technical Support Engineer II to work directly with customers and cross-functional teams on daily support and operational tasks. In this ...

Cyera

Senior Technical Support Engineer

Chicago, IL · On-site +1

$90K - $110K/yr

THE OPPORTUNITY The Senior Technical Support Engineer provides product-focused technical resolution for issues that require deep investigation. This role owns complex troubleshooting within defined ...

Zero Hash

Technical Support Engineer (AMER)

Chicago, IL · On-site +1

About the Job Join zerohash as a Technical Support Engineer and help drive the efficiency of our global value transfer infrastructure. This role is perfect for a detail-oriented professional with a ...

zerohash

Technical Support Engineer (AMER)

Chicago, IL · On-site +1

About the Job Join zerohash as a Technical Support Engineer and help drive the efficiency of our global value transfer infrastructure. This role is perfect for a detail-oriented professional with a ...

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All JobsTechnical Support Engineer JobsExecutive Technical Support Engineer JobsExecutive Technical Support Engineer Jobs in Chicago, IL

Executive Technical Support Engineer information

See Chicago, IL salary details

$38.6K

$81.4K

$123.1K

How much do executive technical support engineer jobs pay per year?

As of Sep 5, 2026, the average yearly pay for executive technical support engineer in Chicago, IL is $81,415.00, according to ZipRecruiter salary data. Most workers in this role earn between $59,700.00 and $101,500.00 per year, depending on experience, location, and employer.

What is an executive technical support engineer?

Executive Technical Support Engineers are specialized professionals who provide high-level technical assistance to key clients, often including executives or major business customers. They handle complex technical issues, ensure rapid resolution, and coordinate with internal teams to address critical problems. Their role often involves direct communication with senior stakeholders, delivering tailored solutions, and maintaining strong client relationships. These engineers typically possess deep technical expertise and excellent communication skills to navigate both technical and business challenges.

What are the key skills and qualifications needed to thrive as an executive technical support engineer?

To thrive as an Executive Technical Support Engineer, you need deep technical expertise in troubleshooting software and hardware issues, a relevant degree in IT or engineering, and experience with enterprise systems. Familiarity with ticketing platforms, remote support tools, and certifications like CompTIA, Microsoft, or Cisco are typically required. Exceptional problem-solving abilities, strong communication, and customer-centricity help build trust and resolve complex issues efficiently. These skills ensure high-quality support for executive clients, uphold service standards, and minimize business disruptions.

What are some common challenges faced by executive technical support engineers in resolving high-priority client issues?

Executive Technical Support Engineers often handle complex, high-impact technical issues for key clients. A common challenge is balancing the need for rapid response with thorough problem analysis, as these cases can require deep product knowledge and cross-team collaboration. Additionally, managing client expectations and communicating technical solutions to non-technical stakeholders can be demanding. Staying updated on evolving technologies and company products is essential for success in this fast-paced environment.

What does an executive technical support engineer do?

An executive technical support engineer provides high-level technical assistance to clients or internal teams, resolving complex issues related to hardware, software, or network systems. They often serve as a liaison between technical teams and executive stakeholders, utilizing troubleshooting skills and technical knowledge to ensure optimal system performance and customer satisfaction.

What are the most commonly searched types of Technical Support Engineer jobs in Chicago, IL?

The most popular types of Technical Support Engineer jobs in Chicago, IL are:

What are popular job titles related to Executive Technical Support Engineer jobs in Chicago, IL?

For Executive Technical Support Engineer jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Executive Technical Support Engineer jobs in Chicago, IL look for?

The top searched job categories for Executive Technical Support Engineer jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Executive Technical Support Engineer jobs?

Cities near Chicago, IL with the most Executive Technical Support Engineer job openings:

Executive Technical Support Engineer jobs near you
Infographic showing various Executive Technical Support Engineer job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 21% Part Time, and 4% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $81,415 per year, or $39.1 per hour.

Technical Support Engineer II

Flywire

Chicago, IL • On-site

Full-time

This job post has expired today. Applications are no longer accepted.

Key responsibilities

  • Manage and resolve customer and departmental support tickets to ensure timely and quality issue resolution.

  • Conduct research using web-based products and command-line tools to diagnose and isolate complex technical issues.

  • Communicate technical information clearly to customers and collaborate with product and engineering teams to address support needs.

Job description

Company Description
Are you ready to trade your job for a journey? Become a FlyMate!
Passion, excitement & global collaboration are all core to what it means to be a FlyMate. At Flywire, we're on a mission to deliver the world's most important and complex payments. We use our Flywire Advantage - the combination of our next-gen payments platform, proprietary payment network and vertical specific software, to help our clients get paid, and help their customers pay with ease - no matter where they are in the world.
What more do we need to truly be unstoppable? Perhaps, that is you!
Who we are:
Flywire is a global payments enablement and software company, founded more than a decade ago to solve high-stakes, high-value payments in higher education. We've since scaled into new regions and industry verticals and expanded our product offerings to deliver meaningful value to our clients around the world.
Today we support more than 5,300 clients across the global education, healthcare, travel & B2B industries, with diverse payment methods across 240 countries & territories and more than 140 currencies.
With over 1,400+ global FlyMates, representing more than 40 nationalities, and in 15 offices world-wide, we're looking for FlyMates to join the next stage of our journey as we continue to grow.
Job Description
The Opportunity
We are seeking a highly motivated and talented Technical Support Engineer II to work directly with customers and cross-functional teams on daily support and operational tasks. In this role, you will support Flywire's Student Financial Services (SFS), eStore, and TPI products for our clients across the U.S. and Canada.
A unique and critical aspect of this role is proactively leveraging AI tools (such as Claude and Gemini) as a smart personal assistant to automate day-to-day TSE workflows, maintain internal repositories, assist with issue investigations, and streamline client communications.
Key Responsibilities:
Technical Support & Troubleshooting
  • Ticket Management: Manage and resolve customer and departmental tickets efficiently, ensuring the highest quality standards while strictly adhering to SLA requirements.
  • Deep Research: Work hands-on with web-based products and command-line tools to thoroughly research and isolate complex support issues.
  • Issue Resolution: Logically assess technical problems, propose accurate solutions to customers, and collaborate with development teams on long-term product enhancements.

Communication & Collaboration
  • Client Communication: Communicate clearly, concisely, and confidently with customers via email or phone, translating highly complex technical issues into easy-to-understand explanations based on the client's technical level.
  • Cross-Functional Liaison: Serve as a highly effective mediator and escalation bridge between customers and the product/engineering teams.
  • Business Alignment: Align technical support goals with Flywire's broader business domain, vision, mission, and strategy to deliver on both short- and long-term goals.

AI & Knowledge Management
  • AI Repository Maintenance: Manage and maintain the TSE team's AI Skills repository, TSE Project Repos, and internal knowledge base.
  • AI Automation: Utilize AI tools to automate routine maintenance tasks, investigate client issues, create bug/product enhancement requests for dev teams, and draft effective, professional client communications.

Qualifications
Here's What We're Looking For:
  • 3-5 years of experience in technical support engineering.
  • 3+ years of hands-on experience with MySQL, Regular Expressions (Regex), and SaaS-based web applications.
  • Proficiency in leveraging AI tools - specifically Claude - to optimize day-to-day tasks and boost operational efficiency.
  • B.S. degree in a science or engineering field.
  • Outstanding verbal and written communication skills.
  • Detail-oriented, highly organized multitasker with a strong eagerness to learn new technologies and a drive to go above and beyond to find root causes.

Preferred Qualifications:
  • A master's degree in a respective science or engineering field is a plus.
  • Experience in higher education, Student Financial Services (SFS), FinTech, or the payments industry.
  • Familiarity with industry-standard logging, analytics, and ticketing tooling.

Technologies & Tools We Use:
  • Core Technologies: MySQL, Java, SaaS Web Applications, HTTP/SFTP Protocols
  • AI Assistants: Claude Code, Google Gemini, Notebook LM
  • Operations & Tooling: Zendesk, Jira, Confluence, SumoLogic, Looker

Additional Information
Submit today and get started!
We are excited to get to know you! Throughout our process you can expect to meet different FlyMates including the Hiring Manager and other Flymates. Your Talent Acquisition Partner will walk you through the steps and be your "go-to" person for questions.
Flywire is an equal opportunity employer and follows a policy of administering all employment decisions and personnel actions without regard to race, color, religion, sex, pregnancy, gender identity, national origin, age, ancestry, physical or mental disability, sexual orientation, genetic disposition or carrier status, veteran status, or any other category protected under applicable national, federal, state or local law.
The US base salary range for this full-time position is $81,000 - $101,000 and benefits. Our salary ranges are determined by role, position level, and location. The range displayed on this job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and several other factors, including job-related skills, experience, relevant education and training.
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