Top Tech Jobs & Startup Jobs in Chicago, IL

Own client discovery, workflow mapping, AI solution design, implementation, testing, UAT, go-live, and post-launch value delivery for retail, e-commerce, hospitality, and restaurant clients. Translate operational needs into product specifications, coordinate engineering and solution teams, define success metrics, manage compliance requirements, travel to client sites, and influence the AI product roadmap through field insights.

Leads and scales a Financial Services and Insurance solution engineering team. Responsibilities include coaching, recruiting, building repeatable pre-sales processes, partnering with Sales, Product, Engineering, Customer Success, and Professional Services, managing KPIs and forecasts, supporting complex enterprise deals, and navigating executive customer relationships, escalations, compliance requirements, and AI-powered SaaS solutions.

Design and implement complex software solutions for clients, leading discovery and scoping sessions, creating statements of work, and translating business requirements into technical solutions. Partner with sales, product, implementation, and engineering teams to address gaps, prioritize roadmap features, improve methodologies, and deliver enterprise IT projects. Provide technical guidance and communicate effectively with stakeholders across technical skill levels.

Own and improve the marketing technology ecosystem, including CRM and marketing automation integrations, ABM orchestration, data enrichment, routing, and workflow automation. Build production AI and API-driven workflows for lead scoring and prioritization, maintain data integrity, troubleshoot sync issues, and document system changes. Enable marketers through self-service dashboards, reporting, and training while partnering closely with Sales and RevOps to improve pipeline efficiency.

Leads enterprise-wide People transformation by designing an integrated operating model across People Operations, Programs, PMO, and Total Rewards. Owns process redesign, AI and automation adoption, workforce planning, governance, systems, data, service delivery, and execution discipline. Builds a scalable global People function, reduces transactional work, improves employee experience, and aligns investments and capacity with business priorities.

Provides senior-level technical support for complex telephony and SaaS issues, leading escalations, troubleshooting integrations, advising developers, and coordinating with Engineering, Product, and Professional Services. Develops JavaScript tools and process improvements, advocates for customer needs, consults with client leadership, demonstrates features, and supports risk mitigation. Requires SIP/telephony expertise, strong communication, customer service, prioritization, and 2–4 years of SaaS support or IT project management experience.

Provides first-line technical support for Talkdesk platform issues, including incident intake, triage, severity classification, troubleshooting, escalation, SLA tracking, ticket management, and customer communication. Supports reporting, workforce management, and quality management applications, including configuration, access control, data verification, recording issues, system monitoring, and integrations. Maintains knowledge-base content and supports government and education customers.

Leads and grows a Commercial Solutions Engineering team responsible for presales strategy, customer-facing solution demonstrations, technical consulting, and solution architecture. Coaches SEs, supports opportunity qualification, partners with Sales, Product, Engineering, and other teams, and drives go-to-market strategy, market penetration, revenue growth, and customer adoption. The role also oversees hiring, organizational development, process improvement, and stakeholder alignment across the global solutions organization.

The General Counsel will provide legal advice on employment law, manage litigation, oversee employee agreements, and ensure compliance with labor regulations. They will also support HR operations and train internal teams.

Lead strategic implementations of Talkdesk CXA and CCaaS solutions, providing technical guidance, integrations, customer adoption support, and post-implementation strategy. Collaborate with customers, partners, Product, and Support teams to ensure project success, resolve issues, and develop deployment playbooks. Serve as a trusted advisor to executive stakeholders while applying expertise in AI, automation, SaaS, APIs, and software integrations.