Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large bank while staying true to the relationship-focused, personalized service of our community banking roots. We serve clients in all 50 states with more than 200 branch banking locations in Illinois, southwestern Florida, northwestern Indiana, west Michigan and southern Wisconsin and commercial banking offices in Chicago, Denver, Milwaukee, Grand Rapids, Mich., and in key branch banking locations throughout Illinois. Our people are the heart of our business and we are proud to rank consistently as a top place to work. Wintrust is a $66 billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol “WTFC.” Why join us? - An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 11 years) and Employee Recommended award by the Globe & Mail (past 6 years) - Competitive pay and discretionary or incentive bonus eligible - Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few - Promote from within culture Why join this team? - This position has the opportunity to interface with and have a positive impact on multiple areas of Wintrust's business - We hold ourselves accountable to high standards, share wins, operate ethically, and have fun Position Overview The Support Analyst provides support, remotely, over the phone, onsite, or via email. They provide technical guidance to customers in response to service requests and accurately document technical issues to facilitate diagnostics and prompt solution. They also manage tickets in the support queue to ensure customers are kept up-to-date and tickets are escalated appropriately. What You’ll Do - Respond to service request queue items and resolve daily service and support requests - Adheres to established service level agreements - Thoroughly documents work performed in ticketing system - Installs, configures, troubleshoots, and repairs desktop and laptop computer systems, peripheral equipment and mobile devices - Follows process documentation and checklists to ensure standardization of work; proactively recommends documentations changes if necessary - Completes project tasks as assigned; meets project dates; schedules installations/upgrades and provides system maintenance in accordance with IT procedures; works on site specific department projects and/or sub-projects Qualifications - Associate’s Degree or equivalent work experience - 0-3 years of desktop support or related work experience - Basic experience working in an Active Directory environment - Proficiency with use of handheld wireless/cellular devices - Basic understanding of Microsoft and Apple PC operating systems also comfortable with contacting third parties for support Benefits Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long-term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance Compensation The estimated salary range for this role is $42.000.00 - $55,000.00, along with eligibility to earn an annual bonus. Actual salaries may vary based on several factors, such as a candidate’s qualifications, skills and experience. #LI-JB1 #LI-Hybrid From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.

Role Description Our client is seeking an experienced Senior Partner Support Engineer to provide advanced technical support to high‑value integration partners and API developers. In this role, you will: - Troubleshoot complex API and platform issues. - Manage high‑priority incidents under SLA. - Serve as the technical liaison between partners and internal engineering teams. - Play a critical role in ensuring smooth integrations and exceptional partner experience. Qualifications - Bachelor's degree in Computer Science, Software Engineering, or equivalent hands‑on experience. - 5+ years supporting customers or partners in a complex SaaS or platform environment. - Experience acting as the primary technical contact for high‑value or embedded partners. - Proficiency debugging in at least two modern languages (e.g., Java, JavaScript/Node.js, Python, C#, Kotlin, Swift). - Strong experience with REST APIs, JSON, XML, SSO (SAML/OAuth/OIDC), and web service protocols. - Demonstrated ability to manage high‑priority incidents under SLA and participate in on‑call rotations. - Proven track record driving bug fixes from initial debug through engineering delivery. - Experience coordinating technical projects across multiple teams or organizations. - Excellent analytical, troubleshooting, and written communication skills for both technical and non‑technical audiences. Requirements - Provide senior‑level technical support to embedded partners across multiple communication channels (support queue, meetings, phone, in‑app, status pages). - Troubleshoot and debug REST APIs, SSO/identity flows, MDM integrations, and platform‑to‑platform data exchanges. - Reproduce issues, analyze logs, triage defects, and drive bug fixes through engineering teams using agile processes. - Manage high‑priority incidents within SLA, including participation in an on‑call rotation. - Support API developers building integrations with the platform, offering guidance on best practices and implementation patterns. - Coordinate cross‑functional technical projects involving Engineering, Product, Customer Success, and Partner Management. - Deliver clear partner‑facing communication, including status updates, rollout plans, and post‑incident summaries. - Contribute to process improvements, documentation, and scalable support practices for partner integrations. Benefits - No Visa Sponsorship. - Contract Duration: 6 months | W2. - Location: Remote (U.S. Based). - Work Schedule: 5AM–2PM PT with one-week 24/7 on call per month.

Role Description We are looking for a Senior Talkdesk Administrator to manage, optimize, and troubleshoot our Talkdesk environment, with a strong focus on its integration with HubSpot. This role is critical in ensuring seamless communication workflows, accurate data synchronization, and overall system reliability for our customer-facing teams. - Manage and maintain Talkdesk configurations, integrations, and system performance - Troubleshoot Talkdesk ↔ HubSpot integration issues, including OAuth authorization failures and token management - Ensure accurate call logging, data syncing, and activity tracking between systems - Diagnose and resolve issues with call recordings not attaching or syncing properly - Support and stabilize embedded dialer functionality and resolve WebRTC/browser-related issues - Fix click-to-call inconsistencies and ensure proper calling provider configurations - Identify and prevent duplicate activities caused by workflows or system conflicts - Monitor system health, API limits, and retry behaviors to ensure platform stability - Collaborate with internal teams to optimize workflows and improve overall efficiency Qualifications - Proven experience administering Talkdesk in a production environment - Strong experience working with HubSpot integrations and APIs - Solid understanding of OAuth, webhooks, and system integrations - Experience troubleshooting VoIP/WebRTC and browser-based dialers (Chrome/Edge) - Strong problem-solving skills with the ability to work independently - Excellent attention to detail and system debugging capabilities Requirements - Experience with CRM workflow automation and optimization in HubSpot (Nice to Have) - Familiarity with API rate limits, retry logic, and integration monitoring (Nice to Have) - Experience working in fast-paced, remote environments (Nice to Have) Project Scope - Immediate focus on stabilizing and optimizing the Talkdesk ↔ HubSpot integration - Ongoing responsibility for maintaining system performance and scaling improvements - Opportunity to expand into broader contact center and CRM optimization initiatives Benefits - Work on a high-impact role supporting critical communication systems - Opportunity to own and improve a key integration within the business - Potential for long-term engagement and growth within a global team

• Provide technical support for JIRA, GitLab, and other IT management tools • Troubleshoot software issues and resolve user access problems • Assist users with cloud-based applications and tools • Respond to tickets and maintain timely issue resolution • Provide training and guidance to end users on system functionality • Document support cases, solutions, and best practices • Escalate complex issues to senior technical staff when needed • Support incident response and system maintenance activities