Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full enterprise sales cycle across the Midwest, from prospecting and territory planning through negotiation and close. Build executive relationships, manage complex multi-stakeholder deals, align tax technology and enterprise software solutions to customer outcomes, and exceed revenue quotas. Use AI-enabled tools and data to improve pipeline development, forecasting, and sales productivity while collaborating with marketing, consulting, sales development, and customer success teams.

Supports customers by analyzing, troubleshooting, and resolving technical issues across enterprise applications, databases, APIs, web services, and cloud environments. Serves as a customer-facing technical resource during implementation and ongoing support, documents solutions, collaborates with internal teams, and participates in training, projects, and on-call rotations.

Leads strategy, execution, and the full lifecycle for tax technology products, from ideation through launch and optimization. Conducts market research, aligns cross-functional teams, drives roadmap and innovation decisions, and identifies integration opportunities across product lines. Uses customer, market, and performance data to guide direction, mentors team members, represents Vertex at industry events, and maintains awareness of competitors. Requires extensive product management experience, SaaS and cloud expertise, strong business acumen, and occasional travel.

Prepare and process 750+ monthly sales and use tax returns for complex clients. Onboard clients, reconcile tax data, resolve compliance issues, manage tax notices, and support electronic filings. Build process efficiencies using Excel, Microsoft 365, VITR, and automation tools. Lead improvement teams, document procedures, mentor junior staff, and communicate with clients while managing peak-period workloads.

Prepare more than 700 monthly sales and use tax returns for complex clients, resolve reporting issues, onboard clients and data files, investigate discrepancies, and support electronic filings and tax authority notices. Maintain compliance reports using Vertex Indirect Tax Returns, Excel, RPA, and Alteryx. Build client relationships, mentor junior staff, and contribute to process improvements while meeting peak-period deadlines.

Own complex enterprise software support cases from assignment through resolution, including executive escalations and critical incidents. Troubleshoot databases, APIs, cloud platforms, ERP and eCommerce integrations, authentication, networking, and infrastructure. Lead root cause investigations, mitigation, recovery, and cross-functional resolution efforts. Document knowledge and troubleshooting procedures, collaborate on defects and fixes, use AI-enabled support tools, mentor team members, and improve support processes while participating in on-call rotations.

Lead enterprise model-training strategy for Commercial AI products: fine-tune LLMs (QLoRA/LoRA/PEFT), train traditional ML models, design large-scale data pipelines, enforce data governance and PII handling, build reproducible experiment/training pipelines, optimize GPU/distributed training costs, and mentor teams to operationalize models into production.

Lead design and implementation of the enterprise AI orchestration and retrieval platform: build MCP servers, define tool-surface and multi-agent patterns, design RAG systems and chunking, implement routing/context/window management and observability, set evaluation and safety standards, onboard product teams, and mentor engineers to raise orchestration and retrieval maturity.

The Software Architect will lead AI quality evaluation, design evaluation frameworks, create risk controls, and ensure compliance, partnering with various teams on AI systems.