Weekend Software Support Engineer Jobs in Chicago, IL

Cooley is seeking a Product Support Engineer to join the Product team, which is part of the larger Innovation group at the firm.

About Cooley: Cooley is a global law firm with an expansive practice and more than 3,000 employees and partners worldwide. We value and celebrate diverse perspectives and strive to create a workplace where every individual can thrive. At the core of Cooley's success is the exceptional talent and unwavering spirit of our people. We embrace individuality while fostering a 'one-firm' culture where collaboration and creativity thrive. Our people are the foundation of our success and the driving force behind everything we do.

Hybrid Schedule: As part of the Cooley culture, we recognize and appreciate the value of being together, in person, to build comradery with others in the office and to be a contributing member of the Cooley office. However, we also appreciate the benefits and flexibility that come from remote working. As such, the default assumption for employees and partners is a hybrid schedule: some in-office presence and some work from home days absent certain essential in-office roles that require five (5) days/week in-office.

Position summary: As a leading technology law firm, Cooley is committed to becoming a leader in the digital practice of law. To support this mission, the Product Support Engineer plays a critical role within the support team by serving as the primary escalation point for complex and technically challenging product issues across Cooley's application portfolio. Under the direction of the Manager of Support and Training, and with guidance from the Associate Director of Product, the Product Support Engineer bridges support and engineering by triaging, analyzing, and investigating unresolved or recurring issues. This role focuses on identifying root causes, validating resolutions, and determining appropriate next steps before escalating issues to product and development teams for final resolution, helping to improve product stability, performance, and quality over time. Specific duties and responsibilities include, but are not limited to, the following:

Position responsibilities:

Advanced Support & Escalation

• Serve as the Level 2+ escalation owner for issues unsolved by product support specialists
• Perform structured triage, including replication, rootcause hypothesis, impact assessment, and recommended next step
• Resolve issues directly when feasible (configuration, small fixes, scripts, workflows)
• For issues requiring engineering intervention, create highquality development tickets with clear problem statements, logs, reproduction steps, and acceptance criteria
• Partner with engineering to validate fixes and support release readiness

Cross-Functional Collaboration

• Act as connective tissue between support, product, engineering, and training
• Communicate trends, recurring defects, and product gaps to product managers
• Participate in agile ceremonies when requested (backlog grooming, sprint planning, bug triage)

Quality, Stability & Readiness

• Identify patterns in escalations and proactively recommend improvements to documentation, training materials, support workflows, or product features
• Contribute to release readiness reviews by validating bug fixes and contributing acceptance notes
• Share knowledge with support specialists and participate in their skill development under guidance of the product support & training manager
• All other duties as assigned or required

Skills and experience:

Required:

• After orientation at Cooley LLP, exhibit proficiency in the Microsoft Office suite, iManage and other firm applications
• Ability to work extended and/or weekend hours, as required
• Ability to travel, as required
• 4+ years directly applicable experience (e.g., application support engineer, technical support engineer, product support engineer, or quality assurance engineer) - Senior level candidates considered with 5+ years' experience with proven ability to operate at an elevated level in terms of scope of responsibility, judgement and autonomy.
• Experience supporting SaaS, enterprise web applications, or custom internal tools
• Familiarity with software development practices, including agile/scrum, version control, and CI/CD awareness
• Strong diagnostic skills across APIs, web applications, authentication, data validation, and system integrations
• Hands-on experience with Azure DevOps, Jira, Confluence, or comparable systems
• Ability to read and understand code (e.g., basic familiarity with scripting languages, JSON, XML, SQL)

Preferred:

• Bachelor's degree
• Experience in Agile/Scrum environments
• Familiarity with cloud platforms (Azure preferred)
• Experience writing or maintaining internal troubleshooting documentation
• Background in QA, systems analysis, or light development
• Familiarity with user research methods, experiment design, and A/B testing
• Experience collaborating closely with product teams to launch new features or products
• Technical curiosity and ability to dive into application behavior, data structures, and systems
• Experience working in a legal services environment with preference to experience in AMLAW 200 law firm or in-house legal department with greater than 50 attorneys

Competencies:

• Excellent communication skills-able to translate technical concepts for nontechnical audiences
• Comfortable with technology and a willingness to learn more
• Highly organized with excellent time management and project management skills and the ability to work independently to meet objectives and deadlines
• Excellent communication skills with all levels of internal and external stakeholders
• Eager to create solutions in addition to identifying problems
• Takes initiative and drives things forward independently
• Deep care for user needs and experience
• Comfortable exploring data to guide recommendations
• Works effectively across teams to achieve shared outcomes
• Comfortable taking responsibility for outcomes and followthrough
• Entrepreneurial by nature
• Excellent attention to detail
• Exceptional interpersonal and communication skills with ability to facilitate and solve problems
• Ability to organize, prioritize and coordinate multiple activities often under tight timelines
• Ability to drive projects to completion and achieve goals
• Strong judgment
• Team-player with collaborative spirit
• Unwavering ability to handle and maintain confidentiality regarding firm information, projects,
• client data
• High level of professionalism at all times
• Proactive, analytical mindset
• Effective presentation skills

Cooley offers a competitive compensation and excellent benefits package and is committed to fair and equitable employment practices. EOE.

The expected annual pay range for this position with a full-time schedule is $120,000 - $175,000. Please note that final offer amount will be dependent on geographic location, applicable experience and skillset of the candidate. Senior level candidates may be considered for this position and would be eligible for a higher salary range based on experience.

We offer a full range of elective benefits including medical, health savings account (with applicable medical plan), dental, vision, health and/or dependent care flexible spending accounts, pre-tax commuter benefits, life insurance, AD&D, long-term care coverage, backup care for children and/or adults and other parental support benefits. In addition to elective benefit options, benefited employees receive firm-paid life insurance, AD&D, LTD, short term medical benefits as well as 21 days of Paid Time Off ("PTO") and 10 paid holidays each year. We provide generous parental leave and fertility benefits. New employees will attend a detailed benefit orientation to learn more about our many benefits and resources.