Top Tech Jobs & Startup Jobs in Chicago, IL

Build and maintain backend product features using Python, Django, and relational databases. Develop APIs, asynchronous jobs, integrations, internal tools, and data-processing workflows while using and critically reviewing AI-generated code. Investigate incidents, resolve customer-impacting issues, improve reliability and database performance, and protect data integrity, security, tenant isolation, and auditability. Own work through testing, deployment verification, documentation, and follow-up while collaborating closely on a small engineering team.

Own the end-to-end development of a secure SMS Adapter connecting retail and grocery store systems, beginning with BRdata, to Ottimate’s AP platform. Responsibilities include sync architecture, retries, conflict handling, local credential security, monitoring, testing, packaging, updates, installation, and deployment on Windows machines. The engineer will work directly with pilot customers to troubleshoot network, permissions, and data-access issues while evolving data models and integrations for additional store systems.

The Corporate Controller will lead accounting operations, month-end close, financial reporting, audits, tax compliance, payment reconciliations, internal controls, treasury, and exit-readiness activities. The role manages accounting systems, automation initiatives, vendor relationships, and accounting team development while partnering with FP&A, Payments, HR, and senior leadership. The position requires strong U.S. GAAP expertise, including ASC 606, audit leadership, AP operations experience, and familiarity with SaaS, payments, or FinTech environments.

Own the technical side of SaaS sales by conducting discovery, tailoring demos, scoping ERP integrations, testing APIs, building lightweight prototypes, reviewing customer data, and addressing technical objections. The role connects sales, onboarding, and product, supports expansions, documents implementation scope, provides customer feedback, and improves SE processes. It requires ERP integration experience, API and data fluency, accounting knowledge, AI tool usage, and strong communication with technical and executive buyers.

Own the strategy, roadmap, and growth of Ottimate’s new product initiatives across procurement, budgeting, spend planning, and contract management. Lead customer discovery, validation, MVP development, launches, and portfolio metrics. Manage product managers and designers, oversee Design and UX, and partner with engineering, data science, sales, marketing, and customer success to deliver coherent, market-ready products.

Develop and close new SaaS business, build sales pipelines, present product demonstrations, negotiate proposals and contracts, exceed quotas, and maintain accurate forecasts. The role targets finance leaders and CFOs, manages mid-market sales cycles, collaborates with internal teams and partners, provides product feedback, maintains Salesforce records, participates in industry events, and mentors SDRs and associate account executives.