Level 2 Support Engineer Jobs in Chicago, IL (NOW HIRING)

Company: ConnexPay
Location: Remote – U.S.-Based | Atlanta, GA | Dallas, TX
Job Type: Full-Time
Reports To: VP of IT Operations
About ConnexPay:
Founded in 2017, ConnexPay is a payments technology company transforming modern e-commerce by bringing PayIns and PayOuts together on a single global platform.
Our technology enables businesses to manage B2B payment needs—including payment acceptance, fraud management, and supplier payments—through one integrated solution. ConnexPay supports a wide range of industries and payment use cases, including global travel, ticketing, insurance and warranty claims, loyalty and rewards, media, and advertising.
At ConnexPay, our culture is built around employee engagement, customer satisfaction, collaboration, and open communication. We believe behaviors drive culture, and culture drives results. We work as one team with a shared commitment to our customers and each other.
 

About the Opportunity:
ConnexPay is seeking an experienced Enterprise Support Engineer II to provide advanced technical support across our enterprise environment.
This is a hands-on Level II support position for an experienced technical professional who can troubleshoot complex hardware, software, Microsoft 365, networking, operating system, and enterprise application issues while also serving as a resource and mentor to Level I support engineers.
The Enterprise Support Engineer II will help improve support processes, analyze ticket trends, manage technical equipment inventory, coordinate support coverage, train users, and collaborate with teams throughout the organization.
This position requires a combination of strong technical troubleshooting skills, excellent communication, independent problem-solving, and the ability to mentor less-experienced support team members.
 

Key Responsibilities:

• Provide Level II technical support for complex issues involving enterprise software, hardware, operating systems, networking, and business applications.
• Troubleshoot and resolve escalated support tickets while maintaining timely and professional communication with users.
• Provide technical guidance and mentorship to Level I Enterprise Support Engineers.
• Share technical knowledge and best practices related to ConnexPay systems and support procedures.
• Design, build, and maintain an effective technical equipment and hardware inventory system.
• Help coordinate support schedules to maintain appropriate coverage during peak periods and critical incidents.
• Develop, document, and implement technical support processes and best practices to improve response and resolution times.
• Analyze support tickets, recurring technical issues, and user feedback to identify trends and opportunities for improvement.
• Recommend and help implement solutions that reduce recurring issues and improve the overall support experience.
• Collaborate cross-functionally with Sales, Finance, Marketing, Development, and other teams to understand technical requirements and support business needs.
• Conduct one-on-one training sessions for employees and users on new systems, applications, processes, and updates.
• Develop reports and monitor key performance indicators (KPIs) related to support efficiency and effectiveness.
• Maintain accurate documentation of technical issues, solutions, procedures, and system information.
• Stay current on emerging technologies, enterprise IT practices, and industry trends.

Required Qualifications:

• Bachelor’s degree in Computer Science, Information Technology, or a related field.
• Minimum of 5 years of professional experience in technical support, systems engineering, enterprise IT support, or a closely related role.
• Hands-on Microsoft 365 experience and knowledge required.
• Demonstrated experience troubleshooting complex technical issues in an enterprise environment.
• Strong knowledge of networking concepts, operating systems, hardware, and enterprise applications.
• Experience working with technical support ticketing systems and remote support tools.
• Strong analytical, troubleshooting, and problem-solving skills.
• Excellent written and verbal communication skills.
• Ability to explain technical information clearly to both technical and non-technical users.
• Ability to work independently, prioritize multiple issues, and operate effectively in a fast-paced environment.
• Ability to collaborate effectively across departments and technical teams.
• Experience mentoring, assisting, or providing technical guidance to junior support professionals.

Preferred Qualifications:  

The following experience is a plus:

• Atlassian software suite
• Microsoft Azure services
• ITIL certification
• CompTIA certification
• Microsoft professional certifications
• Experience developing or improving enterprise IT support processes
• Experience tracking support KPIs and analyzing ticket trends

Benefits & Perks:  

ConnexPay offers a competitive compensation and benefits package, including:

• Unlimited PTO – Flexibility to take time away when needed without a predetermined number of PTO days.
• 401(k) with company match – Immediate eligibility to participate in the company retirement plan.
• Medical, dental, and vision insurance options
• Company-paid life and AD&D insurance
• Flexible work environment – Work remotely from a U.S.-based home or from our Atlanta or Dallas offices.
• Autonomy and ownership – Independence and responsibility within your role.
• Career growth opportunities – Opportunities to advance as ConnexPay continues to scale and grow.

Equal Employment Opportunity:  

ConnexPay is an Equal Opportunity Employer. Employment decisions are made without regard to race, color, sex, age, national origin, religion, sexual orientation, gender identity, veteran status, disability, or any other characteristic protected by applicable federal, state, or local law.