Top Tech Jobs & Startup Jobs in Chicago, IL

Interim VP, Client Success provides executive leadership during a 3-6 month transition to ensure client retention, operational continuity, and team performance. Responsibilities include executive escalation, portfolio health oversight, cross-functional alignment, driving operational improvements, and delivering a transition roadmap for the incoming VP. The role partners with Sales, Product, Legal, Finance, and Executive Leadership to protect revenue and stabilize client-facing operations.

Lead full enterprise sales cycles selling AI-driven supply chain solutions to mid-market and enterprise manufacturers and distributors. Qualify inbound and outbound opportunities, run discovery, technical validation, procurement and close deals. Build repeatable GTM playbook, manage 3–12 month pipelines with accurate forecasting, collaborate with engineers for solution configuration, and relay market feedback to product.

Design, build, and operate production-grade AI systems using ML, LLMs, RAG, and agentic workflows. Define evaluation strategies, implement data/retrieval/orchestration layers, apply MLOps/LLMOps, and partner with stakeholders to prioritize, monitor, troubleshoot, and improve AI solutions balancing quality, latency, cost, reliability, and maintainability.

Own end-to-end release cadences for open-source and managed cloud products. Coordinate engineering, product, QA, DevOps, docs, and customer success. Define quality gates, build release automation and runbooks, mitigate release risks, serve as release contact, and run retrospectives to drive continuous improvement.

Perform day-to-day accounting operations including AP/AR, general ledger, month-end journal entries and reconciliations, support audits, maintain records, and help improve workflows for a growing SaaS company.

Lead cryptocurrency investigations by analyzing on-chain/off-chain data, conducting blockchain tracing, performing OSINT research, reviewing legal process documents, liaising with law enforcement, and training internal teams to detect and remediate illicit activity.

Review, draft, and help negotiate commercial contracts; verify quotes in Salesforce; support RFPs and vendor requests; collaborate with Sales, Finance, Customer Success, and Services; learn Percona product offerings; progressively take on more complex deals and deal‑desk responsibilities under mentorship.

Serve as technical lead for strategic customers: onboard, train, troubleshoot, and optimize Tailscale deployments. Drive adoption via QBRs, provide configuration and integration support, escalate product feedback to engineering, create documentation, and collaborate with sales/product/support to expand usage and ensure long-term customer success.

Lead design, build, and operate enterprise-scale AI/MLOps platform infrastructure. Implement Kubernetes-native systems and infrastructure-as-code, ensure production reliability, security, and cost efficiency, create developer tooling and abstractions, collaborate with customers, mentor engineers, and drive platform architecture and priorities.

Lead and build the company's federal compliance function end-to-end. Drive CMMC, FedRAMP, DoD SRG, and DFARS compliance efforts, define CUI boundaries, author System Security Plans, coordinate engineering/operations to implement controls, manage audits, and maintain continuous monitoring using GRC and security tooling.