Top Remote Senior Level Jobs in Chicago, IL

Build and productionize AI agents for customer support, voice interactions, and carrier onboarding. Develop primarily backend applications in Python and Java or Go, design databases and APIs, integrate frontend components, troubleshoot production workflows, conduct code reviews, and deploy services with Kubernetes. Collaborate with product, engineering, DevOps, US teams, and customers to deliver supply chain platform capabilities.

Leads sales, business development, strategic client management, and project initiatives for key payments merchants in hospitality and entertainment. Builds executive relationships, drives transaction volume and market share, analyzes merchant and industry data, develops client presentations and strategic roadmaps, implements products and marketing initiatives, ensures operational and compliance execution, and manages customer-impacting risks. Requires domestic travel of up to 15%.

Senior Data Scientist responsible for partnering with business leaders to frame ambiguous problems, deliver statistical and machine learning solutions, communicate insights, and drive measurable adoption. The role includes end-to-end analytical ownership, stakeholder influence, executive communication, Agile backlog management, cross-functional collaboration with engineering and technology teams, mentorship, governance, and improving analytics maturity.

Own end-to-end product design for major SaaS features and new offerings, from strategy through launch and iteration. Translate complex AI capabilities into intuitive, trustworthy experiences for accounting professionals. Collaborate with Product, Engineering, and leadership, conduct user research and analytics, create high-fidelity prototypes and specifications in Figma, uphold design-system quality, and mentor junior designers.

Designs, administers, maintains, and supports hybrid cloud infrastructure across Azure, VMware, networks, operating systems, databases, and security appliances. Builds CI/CD pipelines and Infrastructure-as-Code deployments using Terraform or ARM templates, supports Kubernetes and AKS environments, configures Istio and Helm, and develops disaster recovery solutions. Troubleshoots infrastructure and SQL Server issues, improves reliability and cloud costs, maintains operational documentation, mentors engineers, supports tickets and critical incidents, and collaborates with development, client service, and business teams.

Own the company’s full accounting function, including general ledger, monthly close, accounts receivable, accounts payable, payroll, tax compliance, internal controls, and audit coordination. Prepare financial statements, manage SaaS revenue recognition and multi-state compliance, maintain accounting processes, and work directly with the CFO/COO, auditors, tax advisors, vendors, and payroll providers.

Serve as the strategic compensation partner for Sales, advising senior leaders on offers, equity, leveling, promotions, retention, benchmarking, and compensation cycles. Analyze market and internal data, support incentive-plan governance and modeling, lead competitive intelligence, improve compensation programs, manage strategic projects, and develop manager enablement materials. Partner closely with Finance, Sales Operations, Recruiting, Legal, and HR while presenting recommendations to executive stakeholders.

Leads a strategic insights team analyzing product development productivity, operating models, workflows, and AI adoption. Frames hypotheses, conducts quantitative analysis and experiments, evaluates delivery and business outcomes, and translates findings into executive recommendations. Partners with Product Operations, Technology, Product, and Finance to implement actions, track adoption, and measure results. Establishes analytical standards, communicates with senior leaders, and develops a high-performing analytics team.

Owns mid-market merchant sales opportunities from prospecting through contracting, launch, and handoff for Cash App Pay and Afterpay. Responsibilities include account planning, outbound pipeline generation, discovery, business-case development, commercial negotiation, cross-functional deal coordination, Salesforce forecasting, and meeting revenue targets. The role requires consultative selling to senior commerce, marketing, finance, and technology stakeholders, plus market insight sharing and occasional travel.

Serve as a trusted technical advisor to telecommunications carriers and enterprise customers. Design carrier-grade messaging, voice, identity, and fraud-prevention solutions; translate customer needs into scalable architectures and product enhancements; lead technical workshops and architecture reviews; support RFI/RFP responses; and collaborate with Product, Engineering, Sales, Business Development, and Customer Success teams to drive adoption and successful implementations.