Top Tech Jobs & Startup Jobs in Chicago, IL

The Head of Sales will be Modern’s first dedicated seller, responsible for defining and proving its go-to-market motion. This player-coach will generate pipeline, sell across self-serve, mid-market, enterprise, agency, and partner channels, run technical demos, provide pricing and product feedback, and build a repeatable sales playbook. After validating the motion, they will hire and lead a sales team. The role requires strong B2B SaaS sales experience, technical fluency, AI and commerce knowledge, and comfort operating in ambiguity.

Architect and refine scalable cloud infrastructure software for enterprise and internet-scale environments. Responsibilities include developing robust software, designing systems supporting 1,000+ nodes, optimizing performance, and collaborating with distributed technical teams in agile environments.

Supports revenue marketing, brand awareness, and client acquisition through email campaigns, nurture sequences, newsletters, webinars, social media, SEO content, visual design, video editing, reporting, and market research. Collaborates with Marketing and Sales teams to generate qualified interest and improve campaign performance.

Provides high-level administrative and executive support to assigned clients, including inbox and calendar management, scheduling, correspondence, research, data entry, social media management, expense reporting, meeting coordination, and project organization. Serves as the primary client contact, maintains proactive communication, tracks billable hours, manages recurring tasks, and supports timely project completion. The role requires autonomous work, strong organization, responsiveness, and availability during client business hours.

Designs, builds, deploys, and supports full-stack enterprise applications using Databricks and Azure. Develops user interfaces, backend logic, APIs, workflows, secure write-back, reporting, forecasting, planning, and operational tools. Integrates enterprise platforms including SAP, Salesforce, and Power BI. Partners with business, data, and analytics teams, supports production applications, and establishes delivery standards while coordinating offshore development resources.

Leads large-scale HRMS modernization and implementation programs from planning through stabilization. Manages PMO governance, schedules, budgets, resources, risks, stakeholders, vendors, HR system integration, data migration, testing, go-live, change management, training, and adoption. Ensures alignment with business objectives, federal regulations, privacy requirements, FedRAMP, and cybersecurity standards while coordinating HR, payroll, IT, executives, and implementation partners.

Designs and evolves scalable, secure distributed systems and cloud-native microservices architectures. Responsibilities include event-driven architecture with Kafka, GraphQL and mobile/backend integration, Docker and Kubernetes deployment, AWS infrastructure, Infrastructure as Code, security, observability, HIPAA compliance, architecture reviews, threat modeling, documentation, prototyping, and technical enablement. The role partners with engineering, product, and business stakeholders to guide platform strategy and architectural standards.

Lead the global renewals organization and own retention strategy, renewal operations, forecasting, churn reduction, and commercial performance. Develop scalable renewal processes, playbooks, and governance; manage complex enterprise negotiations; improve GRR, renewal rates, uplift, and forecast accuracy; and lead global teams through cross-functional partnerships with Sales, Customer Success, Finance, Legal, Pricing, Product, and Operations. Drive automation, process transformation, executive reporting, and predictable recurring revenue growth.

Own product areas for an autonomous banking platform, translating backend capabilities (APIs, async workflows, ML) into user-facing features. Conduct customer discovery, define technical requirements and acceptance criteria, prioritize backlog, partner with engineering on scoping and de-risking, and validate outcomes using feedback loops and analytics.

The role involves designing, developing, and maintaining software applications. Collaboration with cross-functional teams is expected, alongside optimizing existing systems.