Training Manager Jobs in Romeoville, IL (NOW HIRING)

Cooley is seeking a Product Support and Training Manager to join the Product Team, which is part of the larger Innovation group at the firm.

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. The Product Support & Training Manager is responsible for ensuring that internal teams and end users can successfully adopt, use, and advocate for Cooley's product portfolio. This role provides strategic leadership across product support, training, and enablement, combining deep product expertise, advanced support oversight, and structured learning programs to drive readiness, consistency, and overall product effectiveness across the organization. Serving as a key bridge between product, support, knowledge management, engineering, and customer success, this role delivers a unified experience across the product lifecycle. Responsibilities include overseeing complex issue resolution and escalation processes, establishing effective feedback loops, and designing proactive training and enablement initiatives that support crossfunctional alignment and organizational preparedness. Specific duties and responsibilities include, but are not limited to, the following:

Position responsibilities:

Product Support Leadership:

• Oversee Level 1-3 support workflows, ensuring consistent, highquality responses and escalations across the support team, aligning with similar responsibilities in internal support teams
• Develop onboarding and adoption plans (training, office hours, job aids, communications) for new product launches, major releases, and key customer groups
• Serve as primary escalation owner for complex or highvisibility issues, coordinating with product, engineering, and external vendors when needed
• Monitor support trends, recurring issues, and product gaps; deliver structured feedback to product management and engineering
• Maintain and evolve documentation, troubleshooting guides, workflows, and standard operating procedures
• Establish and report on experience and service metrics (e.g., CSAT, time-to-first-response, time-to-resolution, training completion, adoption/usage signals) and drive continuous improvement

Training & Enablement:

• Own development and delivery of all product-related training programs for internal teams, high-value customers, and business stakeholders
• Conduct regular live and asynchronous training sessions, workshops, and onboarding programs
• Partner with product management to ensure new features are launched with clear adoption guidance, release notes, job aids, demos, and internal communications
• Create role-specific learning paths and certification-style programs to ensure consistent product proficiency across the organization
• Evaluate training effectiveness through feedback and usage metrics; iterate content and delivery to improve outcomes

Product Adoption & Readiness:

• Support demo needs by maintaining demo environments, demo scripts, and standardized talk tracks for key products and features
• Collaborate closely with product management to understand roadmap, feature goals, and success criteria
• Define and execute "product readiness" processes-including training, documentation, messaging, and success measurement
• Track adoption metrics and usage signals; identify and address gaps between intended and actual use
• Partner with the product team to streamline the end-to-end product experience and remove friction points

Cross-Functional Collaboration:

• Act as the connective tissue between product, support, engineering, and business and legal teams
• Serve as a trusted product expert in both internal and external conversations
• Advocate for user needs by synthesizing support data, user feedback, and training insights
• Ensure consistent product messaging across documentation, training, communications, and stakeholder interactions

Knowledge, Documentation & Process Improvement:

• Maintain an authoritative knowledge base: product guides, FAQs, troubleshooting flows, SOPs
• Continuously refine support processes, SLAs, training assets, and enablement frameworks
• Own and optimize documentation for new and existing products, ensuring accuracy, clarity, and alignment with product intent

Team Professional Development:

• Serve as direct supervisor and mentor to direct reports
• Provide day-to-day supervision of direct reports, ensure compliance with assigned work hours and monitor for compliance with all firm and department policies. Manage staffing coverage, review and process time logs/time off requests
• Support business professional development and continued educational opportunities
• In collaboration with immediate supervisor and central HR, participate in hiring, performance appraisals, counseling, termination and other employee lifecycle events
• 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
• 5+ years applicable experience in the field (e.g., web-based applications support, applications training and management of knowledge bases and help content)
• Experience supporting SaaS, enterprise web applications, or custom internal tools
• Familiarity with software development practices, including agile/scrum, version control, and CI/CD awareness
• Experience in Agile/Scrum environments
• Experience writing or maintaining internal troubleshooting documentation

Preferred:

• Bachelor's degree
• Supervisory experience
• 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)
• Familiarity with cloud platforms such as Azure
• 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:

• A builder mindset which thrives on observing processes, products, software applications, etc., with the ability to find ways to improve processes and applications
• Strong organizational skills and attention to detail
• Analytical mindset with a passion for problemsolving and continuous improvement
• Empathydriven approach to customer engagement with strong customeradvocacy instincts
• Ability to mentor peers and model highquality support behaviors
• Entrepreneurial by nature
• Exceptional interpersonal and communication skills
• 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
• Demonstrated ability to lead through influence and develop talent
• 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. Senior level candidates may be considered for this position and would be eligible for a higher salary range based on experience. Please note that final offer amount will be dependent on geographic location, applicable experience and skillset of the candidate.

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.